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Lieutenant Thomas Conrad was standing in a control room in Nashville’s new central jail when he noticed something off with one of the key rings hanging on the wall. It was midday on December 30, 2019, and in two weeks the still empty jail would take in about seven hundred inmates. While contractors were finishing their work, Conrad, a senior correctional officer with the Davidson County Sheriff’s Office, was organizing equipment: handheld radios, handcuffs, and keys. Conrad had been an infantryman in Iraq, where he’d learned to spot slight inconsistencies in the landscape. Looking more closely at the key ring, he realized what was wrong: it was circular. All the others were horseshoe-shaped.

The key rings were fastened with hard plastic locks. The lock on the circular ring, Conrad saw, was cracked. On each key ring was a disk stamped with the number of keys that should be in the set. The disk on the circular ring was stamped “18.” Conrad counted the keys three times: there were only sixteen. He phoned Lieutenant Timothy Dial, the jail’s key-control officer, and said, “I’m going to need you to come down here.”

Dial arrived. “We don’t use rings like this,” he told Conrad.

“It’s got to be maintenance,” Conrad said. Speculating that a cleaner had somehow broken the original key ring, he radioed the maintenance crew.

The plastic lock on the mysterious key set was yellow, signifying “restricted,” because it held a general-movement key that could open almost any door in the jail. Dial consulted a key-inventory spreadsheet; the general-movement key was one of the two that were missing.

A maintenance crewman arrived. “It wasn’t us,” he said.

The Downtown Detention Center, as the new jail was called, had been under construction for more than three years. Once open, it would house every arrestee in Nashville. The building occupied a block near the state capitol, on a plot of land where Nashville’s old central jail had stood for thirty-five years. That jail, notoriously violent and corrupt, had symbolized the good-ol’-boy era of Nashville law enforcement, and the Downtown Detention Center was replacing it both physically and symbolically. The new jail had tablet computers for inmates and a behavioral-care center for mentally ill arrestees—the first of its kind in an American jail. The facility reflected changing attitudes toward criminal justice in Nashville, which in recent decades has become a tourism and business destination and a progressive bastion in a state sometimes called “the buckle of the Bible Belt.”

At 2 P.M., Conrad and Dial met with Brian Beazley, the jail’s electronic-security officer, who managed its surveillance cameras. Beazley pulled up footage from the control room that housed the keys, zoomed in on the hook where Conrad had found the circular key ring, and pressed Rewind. The footage showed nothing unusual until December 27th at 12:54 P.M.—three days earlier—when the circular ring suddenly disappeared from its hook. Beazley rewound another few seconds. A purple hand appeared in the frame. “What the hell?” he said.

They pulled up the same moment as recorded by another camera, which showed a wider view. The purple hand was attached to a man they didn’t recognize. He appeared to be a laborer, wearing a hard hat, a reflective vest, and purple nitrile gloves. Laborers weren’t allowed in the key-control room.

They rewound to 10:44 A.M., pressed Play, and watched as the laborer walked in. Short and of slight build, he carried a bucket. His face was obscured by glasses and a dust mask. This was strange: the pandemic was still months away, and most of the construction tasks requiring a mask—plastering, insulation—were finished. Conrad and Beazley watched as the man grabbed a key set and tried, unsuccessfully, to pry open the lock with a screwdriver. At 10:57 A.M., he pocketed another set, with a yellow lock on its horseshoe ring, and left the room. At 12:54 P.M., he returned and replaced it. The lock was still yellow, but now the ring was circular.

Tony Wilkes, the chief of corrections at the Davidson County Sheriff’s Office, was overseeing the jail’s construction. He got word of the incident to the sheriff himself, Daron Hall, who was in Florida for the holidays. Hall had worked in the sheriff’s office since the eighties. As a case manager at the old jail, he’d known of beatings, murders, suicides, sadistic officers. After he was elected sheriff, in 2002, he began envisioning a more humane jail. Hall believes that incarceration can provide inmates with “better opportunities.” He dislikes the word “rehabilitation.” He told me, “Rehabilitation assumes there was habilitation. A lot of these people had no chance to make it.” The new jail, a hundred-and-seventy-five-million-dollar project, was the culmination of Hall’s career. He was staking that career, along with any future he might have in state politics, on the jail’s success. Some Nashvillians had begun calling it Hall’s “baby.”

Beazley continued reviewing footage, and noticed that the infiltrator’s reflective vest bore the insignia of the security firm that had installed the cameras. Beazley showed a still image of the man to a firm supervisor. He didn’t recognize him. Nobody did. Wilkes briefed Hall, who said, “We have to find him.” Conrad and Dial showed still images to the others at the jail, and devised a plan of capture should the man return.

Hall waited for five days, thinking—at times hoping—that he might never hear of the infiltrator again. But, on January 4, 2020, someone appeared outside the jail’s lobby. The officer on duty, Cory Witkus, recognized him with a jolt. The man was wearing a dust mask and carrying an Igloo cooler. Witkus, having been warned that the infiltrator might be armed, kept in mind the Glock on his utility belt as he buzzed him in.

“Hey, what do you have going on today?” Witkus said, casually.

“I’m here to work,” the man in the mask said, in a soft, cordial voice.

Witkus offered to show him to where other laborers were working, and the man thanked him. Witkus led him to a passageway whose windowed doors, on either end, could be locked remotely. He instructed the man to proceed to the far door. Once the man was inside, Witkus slipped back out and radioed officers in the master control room, telling them to keep the doors locked, then radioed Dial and Conrad. The police were called as Conrad raced to the passageway, arriving as the man was trying to open the far door.

The man smacked the window. “Let me out!” he yelled. “I’m here to work!”

He rushed back to the first door and, finding it locked, began pacing. After ten minutes, he came to a sudden halt. He pulled a piece of paper from his pocket, lowered his dust mask, stuffed the paper in his mouth, and chewed. He pulled another piece of paper from his wallet and chewed that, spitting the wad into a trash bin.

He had been locked inside for forty-five minutes when police entered the passageway, followed by Conrad, Wilkes, and Dial.

The police asked the man his name. He didn’t respond.

Conrad told him to remove the mask. He didn’t move.

“Man, take that mask off,” Wilkes said angrily.

Conrad pulled down the mask. The man gazed at Wilkes, whose expression went from exasperation to shock.

“That’s Alex Friedmann,” Wilkes said.

The man silently looked at the floor.

Wilkes phoned Hall’s chief of staff. “You’re not going to believe this,” he said. “We got Alex freaking Friedmann.”

When news of the arrest got out, people who knew Friedmann were similarly shocked. So were those who only knew of him. Friedmann was one of the most respected prison-reform activists in America. He was the associate director of the Human Rights Defense Center, a prisoners’-rights organization, and the president of the Private Corrections Institute, a watchdog group that monitors the for-profit-prison industry. He was the managing editor of Prison Legal News, a newspaper written by and for inmates. He often addressed the Tennessee legislature and had testified before Congress. He’d spoken at A.C.L.U. and N.A.A.C.P. conferences, lectured at law schools, and consulted on prison legislation for Bernie Sanders.

Friedmann was the sort of activist that people who normally can’t abide activists could appreciate. He seemed more like a professor, maintaining a neat white goatee, and wearing button-down shirts, ties, and rimless glasses. Allies and critics alike described him as brilliant and single-mindedly devoted to his cause, yet also as so rational and eloquent that he won over law-and-order conservatives and recalcitrant public officials. He could be vain, but he was better known for his gentleness.

John Ray Clemmons, a legislator in the Tennessee House of Representatives, described him to me as “someone who just cared very deeply.” Janet Wolf, a fellow-activist in Nashville and a close friend of Friedmann’s, mentioned “how incredibly wise he was in trying to help other people understand” the plight of prisoners. Demetria Kalodimos, a former news anchor on Nashville’s NBC station, told me that Friedmann was one of her best contacts for criminal-justice stories; she valued him both as a source and as an on-camera expert, because he “spoke the language of a lawyer,” not of a social-justice warrior. Friedmann, a member of Mensa who taught himself civil case law, could write like a lawyer, too, in briefs and legal articles. He could also write like an author. He was a guest columnist at the Tennessean and had won a PEN America award for playwriting.

People especially trusted Friedmann’s expertise because they knew he’d earned it through experience. When he was eighteen, he had been charged with armed robbery and attempted murder, and he had been imprisoned for nearly a decade.

Prison-reform activists tend not to call incarcerated people “prisoners” or “inmates,” preferring the term “insider,” with its more flattering connotations of hard-won knowledge. Friedmann was the insider’s insider. His condemnation of the American penal system came out of his time in brutal detention facilities, including Nashville’s old jail. Through pertinacity and patience, he’d penetrated the corridors of power.

But prison hadn’t turned Friedmann into an abolitionist. He objected not to the existence of prisons but to their conditions. Jeannie Alexander, another Nashville activist and friend, who is an abolitionist, told me that she couldn’t interest Friedmann in sit-ins that she organized. “He was never going to start a riot,” she said. “He always worked with the system.” Friedmann had improved the lives of countless American prisoners through the courts, the legislative process, and the press. Like Hall, he believed that penitentiaries, if managed humanely, could better inmates; he was living proof.

Nobody was more surprised by Friedmann’s turn back to crime than Hall. The two had first met a year and a half before Friedmann’s arrest at the jail, but they’d known each other by reputation long before that. Hall had worked as a case manager at Nashville’s old jail while Friedmann was locked up there. Later, Hall worked for Corrections Corporation of America, which operated another prison where Friedmann was incarcerated. When Friedmann got out and became an activist and a journalist, he often consulted with Hall’s staff. In 2018, the sheriff’s office invited Friedmann to join a group of outside advisers on jail reform, and in the months before Friedmann’s arrest Hall had met with him many times. He appreciated Friedmann’s seriousness, and the feeling was mutual. Friedmann lauded Hall in the Tennessean. When he learned of the arrest, Hall said, he “couldn’t believe it.”

Hall’s chief deputy at the time, John Ford, told me that the arrest “was a holy shit moment,” adding, “He’s been in and out of our jails, he’s been in meetings with us, and he’s doing this—right behind our backs?” Ford didn’t know what Friedmann had been up to in the jail, but sensed that he “was getting ready” to commit an awful crime.

On the afternoon of his arrest, Friedmann phoned his wife, Alice. He didn’t sound like a man with a sinister plan. His affect was dainty, and his voice was as soft as it had been when he’d greeted Witkus in the lobby. “Hello, dear,” he said on the call, which was recorded. “I have been arrested. Do not get terribly concerned.” He asked Alice to fetch a pencil and paper. After she retrieved them, he said, cheerily, “Good deal.” She asked why he’d been arrested. “They’re charging me with burglary and destruction of evidence, which sounds rather far-fetched,” he said. When she suggested raising cash for a bail bond, Friedmann offered the only hint that he was in deep trouble. The problem with a cash bond was that “they don’t return it until the entire case is disposed of—which might take a good long while.” Nevertheless, Alice put a five-thousand-dollar down payment on a bond, and Friedmann was released that night. His lawyer handed over the missing jail keys.

Friedmann was charged with attempted burglary, possession of burglary tools, and evidence tampering. In his cooler, police had found a horseshoe-shaped key ring and a bolt cutter. From the trash bin in the passageway, they retrieved the papers Friedmann had chewed. The markings on one were still legible: it was a hand-drawn schematic of the jail.

Most county-sheriff offices function much the way police departments do—investigating crimes, making arrests, and jailing people. The Davidson County Sheriff’s Office, which presides over the Nashville area, only does the last: a few officers serve warrants and provide security, but fully half of the office’s staff of twelve hundred look after inmates.

Daron Hall is the antithesis of the stereotypical Southern sheriff: he doesn’t like guns and it’s nearly impossible to find a photograph of him in uniform. He prefers to present his six-foot-four frame—he was a kicker on his college football team—in well-tailored suits. With his open, often smiling face, white goatee, receding hairline, and glasses, Hall looks more like a politician than a sheriff. Now sixty-one, he has been in the position longer than anyone else in Davidson County history, and he inspires fierce loyalty in his staff, many of whom have been with him since his first election. They trust Hall for the same reason that Friedmann’s admirers trusted Friedmann—Hall is devoted to his work and very good at it. Back when his reëlection was not guaranteed, he campaigned on the slogan “It’s what I do.” Like Friedmann, Hall can be self-important: the website of the sheriff’s office lists every predecessor of his since 1783. The vanity is tempered by compassion. Even Nashville conservatives don’t mind that Hall is a reform-minded Democrat who opposes the death penalty. (“I don’t think it’s the right thing until they execute rich people,” he told me.)

The Nashville police assigned a veteran detective, Robert Anderson, to the Friedmann case. In the second week of January, 2020, he sat down with Beazley, the electronic-security officer, who was still combing through footage from the jail’s cameras.

He was startled to find that Friedmann had been infiltrating the jail for months. His image popped up everywhere. Sometimes he was dressed as a supervisor, carrying a clipboard and wearing a dress shirt and khakis. Other times he impersonated a laborer, in a Hard Rock Café T-shirt and jeans, carrying a bucket. He wore an assortment of hard hats and reflective vests. One feature never changed: the dust mask. Video from cameras on the jail’s exterior showed him walking to and from the jail in the mask. He could even be seen wearing it in a brief clip in which he was driving by the jail. Beazley marvelled at his discipline.

At the same time, Friedmann was brazen. He occasionally climbed a ladder to cover a camera. Otherwise, he let himself be recorded, as though he wanted his ingenuity documented. He painted and used a drill and a grinder, but it wasn’t clear from the videos just what he was working on.

After reviewing video for nearly a month, Anderson went into the jail with an investigator from the Nashville Police’s Crime Scene Investigation Section. In a recreation room where Friedmann had been recorded working on a cinder-block wall, they noticed that the mortar between certain blocks was crooked. The blemishes were subtle enough to escape the notice of anyone not looking for it. They found similar blemishes around the jail.

They met with Conrad in the visitation room. In ten booths, separated by cinder-block partitions, inmates could chat with visitors through glass while seated at metal counters. Friedmann had been recorded kneeling for long periods below the counter in booth No. 2. The investigator got on her knees and noticed that the white paint on one cinder block in the partition was less glossy than the paint on the others. She hit the block with a hammer. It crumbled easily. She pulled a plastic package out of the resulting hollow. Inside were a razor blade, three handcuff keys, and a security bit, a device used to fasten fixtures. Also in the hollow were a fully loaded revolver and ten spare cartridges.

Everyone fell silent. Even when Conrad had served in Iraq, the sight of a gun hadn’t been so jarring. “When we found that first gun, things changed,” he told me.

Conrad, Anderson, and the investigator proceeded to a holding cell where Friedmann had been recorded cutting around a metal mirror on a wall. The investigator pulled off the mirror, revealing a false wall and, behind that, another package. This one contained a razor blade, three handcuff keys, and a fully loaded pistol, with eight spare cartridges. Behind a metal mirror in a bathroom: another fully loaded revolver and eleven cartridges.

The police notified Friedmann’s lawyer, and on February 18th Friedmann surrendered to officers at his home. At a press conference announcing the arrest, it was clear that any respect Hall had once felt for Friedmann was gone. His anger and sense of betrayal were obvious as he told reporters, “It was discovered that Mr. Friedmann, over many months, had developed and implemented an extremely deliberate—and, in my opinion, evil—plan.” He added, “I’m not confident that we have found everything.”

In fact, he knew they hadn’t. Friedmann had “worked” in all of the jail’s fourteen cellblocks. Hall didn’t have the equipment to properly search behind walls; the police didn’t, either. The F.B.I. did, and Hall asked for its help, but when Matt Foster, an agent in the Bureau’s Nashville office, visited the jail, the challenge posed by Friedmann’s scheme left him dumbstruck. “This is nuts,” Foster said to himself. He had seen jailbreak cases, but he’d never heard of a case of someone breaking into a jail, much less into one that was four hundred thousand square feet, to deftly plant guns in its infrastructure. “Nobody had—I searched our files,” he told me, referring to the F.B.I.’s case-file corpus, which dates back to 1908.

Foster didn’t see how the jail could be secured without tearing it apart. Nor did Hall, who feared that his “baby” would have to be demolished before it had opened.

A judge set Friedmann’s bail at two and a half million dollars. Given his proven ability to sneak in and out of the sheriff’s newest maximum-security jail, Hall didn’t want to risk housing him in any county facility, so he was sent to Riverbend Maximum Security Institution, a state prison in Nashville. He was put in solitary confinement. (His wife and his lawyer could visit.) Friedmann, who was about to turn fifty-one, sat on the wall-mounted bunk, thinking about how he’d ended up there.

Alexander is the only child of Toni Jo Friedmann, a Tennessean, and Victor Friedmann, who grew up in Denver, where his parents, Croatian Jews, landed after fleeing the Nazis. Victor attended Harvard and was completing a master’s in the Department of Aeronautics and Astronautics at M.I.T. when Alexander was born, in 1969. The family moved to Saudi Arabia, where Victor worked as a geophysicist at Aramco. They lived in the company’s gated community in Dhahran.

Yearbook photos from the community’s grade school show a smiling, demure young Friedmann. He kept to himself, reading and drawing. The one classmate I found whom he befriended, Craig Proctor, told me that, to the few people he let in, Friedmann was kind and generous, though never exactly warm. He dressed in button-downs, like an adult, and had a manner that was courtly beyond his years, as well as a keen sense of injustice. He defended kids who were bullied, though his anger was always “very controlled,” Proctor said. Small for his age, Friedmann didn’t fight the bullies; he taunted them with his superior vocabulary—he’d “bludgeon with words,” Proctor told me, adding that Friedmann “thought he was smarter than other people.” Proctor sensed a severe tension between Friedmann and his father but didn’t know its origin.

There was no high school in Dhahran, so Friedmann’s parents sent him to Mercersburg Academy, a boarding school in Pennsylvania, where he became depressed. Proctor, who also attended the school, found one thing that could animate his friend: playing Dungeons & Dragons. Friedmann talked compulsively about one of his avatars, a thief rogue. It seemed to Proctor that Friedmann wanted to live in the game. Friedmann’s time at Mercersburg ended during his second year, when he attempted suicide by drinking chemicals. He was committed to a series of psychiatric hospitals.

In a court-ordered examination later conducted by a psychologist in Nashville, Friedmann traced his decline to his father, saying that he was strict and intellectual and never saw his son as a real person. He reënacted for the psychologist a scene of Victor forcing him to sit at the piano while commanding, “Practice, practice.” The psychologist concluded that Friedmann was “a rather sad man,” aloof and distrustful but also prone to “an upsurge of disruptive ideas.” She added, “An intellectual assessment was not done because it has already been determined that Alex has ability well above average.”

Friedmann and his mother moved to Nashville in 1986, when Friedmann was seventeen. Toni Jo’s mother lived there, and Victor was still working in Saudi Arabia. Friedmann’s inner turmoil turned outward. He began behaving erratically, holing himself up in his room. Toni Jo, fearing that he intended to harm her, called the police. Officers discovered a cache of handguns. Friedmann claimed that he’d found them. He wasn’t arrested, but Toni Jo was frightened enough to relinquish custody of him and return to Saudi Arabia.

Friedmann, still a minor, became a ward of the State of Tennessee. Lawyers at Davidson County’s juvenile court found the presence of this bright, courteous young man puzzling. He began attending the Tennessee Preparatory School, a state-run residential school for delinquent and neglected children, which had a forbidding reputation. Administrators shaved the heads of boys who tried to run away. Before Friedmann arrived, two students killed themselves. A student sued the school, alleging that he was being kept there against his will, and the Tennessean reported that it was run “like a correctional institution.”

In 1987, on the day after Thanksgiving, Friedmann appeared at the locked glass door of the Coin Purse, a numismatic shop in Nashville. He wore a wig and a false mustache, and carried a duffelbag containing a pistol. When the store’s manager, Mike Gambill, buzzed him in, he noticed the wig and felt a pang of pity, assuming that Friedmann was a cancer patient.

Man looks up at angry woman wearing dress covered in text that reads “No honey that dress does not make your shoulders...

Friedmann asked Gambill to show him some gold coins in a display case. Gambill reached down to retrieve them. When he looked up, Friedmann was holding the pistol inches from Gambill’s forehead. “Clasp your hands behind your neck and face the wall,” Gambill recalls him saying. Gambill had fended off inept robbers, but he sensed that Friedmann, despite his amateurish disguise, was not inept. “The way he was instructing me on what to do,” Gambill said, suggested that he “knew exactly what he was doing.”

As Friedmann stuffed coins into the duffelbag, he asked Gambill where he hid cash. Gambill said that the only cash was in the register.

“Lie to me and I’m going to kill you,” Friedmann said.

Twice more, Gambill recalls, Friedmann threatened to kill him. “I had to make a decision,” the manager told me. “Am I going to die with a bullet in the back of my head or one in the front?” He had a revolver tucked into his waistband, hidden by his blazer.

Two customers, a father and his adult son, appeared outside the door. Friedmann waved them off. They moved away but, sensing that something was amiss, didn’t leave. When Friedmann turned back around, Gambill was pointing his revolver at him. Gambill fired, and a shootout ensued, shattering the glass cases and filling the shop with smoke. Gambill hit Friedmann’s left hand. Running outside, Friedmann, who had not emptied his gun of rounds, fired at the customers, missing both.

In a parking lot, Friedmann was cornered by police. One officer, Rob Forrest, aimed a revolver at Friedmann, who raised his hands in surrender. His wig had flown off, but the fake mustache dangled from his lip. Forrest told me that, though Friedmann looked ridiculous, he behaved like a seasoned criminal, refusing to say his name or answer questions.

Forrest searched Friedmann and found a push dagger embedded in his belt buckle. In his breast pocket were what looked like two pens. Forrest removed the cap of one and found a switchblade. Under the other cap was an aerosol button. Forrest pushed it and winced as tear gas sprayed.

“He was like James Bond,” Forrest told me. “I’ve never seen anybody anywhere close to this type of preparation for a struggle.”

Forrest brought Friedmann to a hospital, where his wounded hand was treated. Eventually, Friedmann identified himself and confessed. “He didn’t have any emotion in his voice,” Forrest recalled. “It just seemed like he was unfazed by the events going on around him.”

Friedmann, who was charged with armed robbery and three counts of attempted murder, was sent to Nashville’s old central jail.

The jail had been a blight on the city for more than a century. In 1883, after an inmate wrote in to the Nashville Banner to ask whether “the people of my own dear county have an idea” of their “loathesome” jail, the state board of health found that the facility was dangerously overcrowded, with prisoners packed into the basement. Tennessee had one of the worst penal systems in America, and the problems continued well into the twentieth century. In 1983, riots swept through the state prisons. After inmates sued over the dismal conditions, the Tennessee Department of Correction came under federal oversight.

By the time Friedmann was locked up, the central jail had been rebuilt and rechristened the Criminal Justice Center—a name whose ironies were well known to Nashvillians. Designed for six hundred inmates, it sometimes held twice that many. Some slept on mattresses on the floor of a tunnel. Tennessee state law doesn’t require much of jails, stipulating that they be “properly heated and ventilated, and have sufficient sewerage,” but the jail couldn’t manage even that. Sweltering in the summer, freezing in the winter, it routinely flooded with raw sewage. Hall described it to me as “a mess.”

When Tony Wilkes, who would become Hall’s chief of corrections, started as an officer, around the time that Friedmann was jailed, he received no training. The most sadistic of his colleagues formed a group, known as the Goon Squad, which beat inmates. The torture took place on an elevator that had a habit of getting stuck. When the doors finally opened, Wilkes recalled, victims “would literally crawl off the elevator.” NBC News aired footage from the jail showing a mentally ill man being hosed with chemical spray, tackled, stripped nude, and put into restraints.

Friedmann went inside on November 30, 1987. He was barely out of boyhood, myopic, five feet seven, and pencil-thin. Friedmann, with whom I have corresponded by mail, described the jail, with his typical wryness, as “a fairly squalid and brutal place.”

It was worse than that. Friedmann tried to kill himself again. He was classified as a “special needs” inmate and assigned a sympathetic case manager, Constance Taite, who told me that she, too, was appalled by the jail’s conditions. After she saw officers beating a shackled inmate, she said, “I would get ready for work and I would start crying.” Of the thousands of inmates she interacted with, Friedmann stands out in her memory. Like the lawyers who’d met him in juvenile court, she found his presence in the jail incongruous.

They shared a love of reading. Taite was going through a Dean Koontz phase at the time. When she finished a thriller, she’d give it to Friedmann. He would read it in a night and want to discuss it the next day. Taite enjoyed their conversations, but she noticed that Friedmann never brought up the fact that he’d almost killed three people, or that he’d been shot and nearly killed himself. He seemed as unfazed as he’d been when he was arrested.

Like other states around the country, Tennessee was closing its public psychiatric hospitals, and mentally ill people who acted out were simply being jailed. Though Friedmann didn’t seem deranged to Taite, she felt that he must be troubled in some way. “Here’s this quiet, intelligent, articulate young man, who gets his ass thrown in jail for bizarre behavior,” she said. “He wasn’t manifesting symptoms of mental unwellness, but you thought there must be something going on.”

Hall began working in the jail a few months after Friedmann arrived. They didn’t meet at the time, but their lives intersected in other ways. Like Friedmann, Hall had a difficult relationship with his emotionally distant father, a salesman and a Nashville city councilman. And, like Friedmann, he liked a good crime thriller. He’d been inspired to go into law enforcement after reading Vincent Bugliosi’s “Helter Skelter: The True Story of the Manson Murders.” He reread it many times, always coming away fascinated and frustrated. “I kept thinking, If I keep reading this, it’s going to say, ‘And he was born with twelve toes,’ ” Hall recalled. “I really thought there was going to be an answer to why he did it.” But Manson was inscrutable. Hall couldn’t accept that. He kept asking why. Why do people end up in jail? Why do they so often return to it? He took girls on dates to the Nashville night court. Hall told me, “The ‘Why?’ is who I am.”

While studying criminology at Western Kentucky University, Hall worked for the Kentucky court system, travelling to small-town jails to determine if arrestees should be granted pretrial release. He interviewed them for hours, learning about their lives. He had expected, even hoped, to meet career criminals. Instead, he met many poor people, mentally unwell people, desperate addicts, and ordinary people who had just made the biggest mistake of their lives. “I saw people who didn’t have horns,” he said. “I saw me.”

The arrestees were often respected members of their communities. They were treated with dignity by local sheriffs, who allowed some of them to be temporarily released at Christmas. Hall’s ideas about incarceration changed. A jail didn’t have to be the worst place in town. “Jails are supposed to be a microcosm of your community,” he said, like a school or a church. If run properly, jails could even be a way to give people failed by those other institutions a new start. Hall learned that his job required, as much as anything, the capacity to forgive.

He was using his field work as the basis for a master’s thesis when, in 1988, he took the job at the Criminal Justice Center, which was offering no one a new start. At the time, Nashville was known to the outside world as a harmlessly boisterous place with good music. But in its political culture the corruption was inescapable, and, like the city itself, carnivalesque. A former governor, Ray Blanton, had gone to federal prison for selling liquor licenses. A onetime majority leader of the Tennessee House of Representatives, who had won reëlection from a jail cell, would soon be imprisoned for his role in a criminal ring that traded in illicit bingo licenses. The beau ideal of local graft was Hall’s boss, Fate Thomas, the Davidson County sheriff. Thomas so thoroughly embodied the city’s official venality that Nashvillians took to calling him Boss Hogg, for the character in the “Dukes of Hazzard” TV show. For years, he was investigated by the F.B.I. for diverting public funds to pay for personal expenses and for using county employees to staff, among other things, his private barbecues. Locals revelled in his notoriety. A cover of Nashville magazine showed Thomas holding a cowboy hat and a cigar, a six-shooter on his belt, with the headline “Why Do the Feds Want to Lock Him Away in His Own Slammer?”

Thomas’s corruption might have been more entertaining if it hadn’t resulted in so much suffering and criminality in his jail. Recidivism was chronic—the same people reappeared in Hall’s caseload year after year. He told me that it was like “picking up sand with a fork.” He wasn’t surprised when one of the inmates he worked with successfully sued the sheriff’s office over the jail’s conditions. The office came under federal oversight in 1990. The same year, Thomas was convicted of misusing his office for private gain and sentenced to five years in federal prison.

After the shootout at the Coin Purse, Friedmann was in the Criminal Justice Center for about two weeks, until his grandmother secured his release with a bail bond. He went to live with her in Antioch, the Nashville suburb where Hall had grown up. But, when she found a reservation for a one-way ticket to Australia in his room, she realized that he meant to flee the country and leave her on the hook for the bond. She called the bondsman, who returned Friedmann to jail, where he tried to kill himself a third time, with pills.

A judge ordered a psychiatric evaluation. A psychologist concluded that Friedmann suffered from dysthymia, today known as persistent depressive disorder, and schizoid personality disorder, writing that he showed “indifference to social relationships and a restricted range of emotional experience and expression.” He also had a tendency to “blur fantasy with reality.”

Friedmann was convicted of armed robbery and attempted murder, which would normally bring extended prison time in Tennessee. But the judge, perhaps taking pity on him, sentenced him to twenty years of supervised probation. He moved back in with his grandmother, took a vocational course in word processing, and worked as a clerk and an industrial packer. The psychologist who’d evaluated him gave him weekly counselling for depression, and he attended group therapy. He seemed to be improving.

However, in 1991, Friedmann, now twenty-two, robbed a comic-book store and then tried to steal trading cards from a Kroger supermarket. When a security guard confronted him, he brandished a pistol, ran outside, and drove off. Police followed him, and he crashed. The arresting officer recovered the pistol, then discovered a razor blade made to resemble a business card in Friedmann’s wallet. In his shirt pocket, the officer found a pen that was actually a stabbing pick. A knife was tucked in his shoe and handcuff keys were hidden on his belt and under a shoe sole. He had a portable cassette player with a hidden compartment for a gun. When the officer asked Friedmann how he’d stashed the weapons so cunningly, he said that he’d learned to do it while jailed in the Criminal Justice Center.

He came before the same judge who’d let him off with probation. Friedmann said of the latest incident, “I see it less as an aggravated robbery, more as an ‘armed escape’ after being caught, motivated by fear and guilt.” He confessed, “I have deep compulsive problems that I do not understand.”

The prosecutor in the case, Dan Hamm, found Friedmann’s presence in the courtroom just as perplexing as Constance Taite and the lawyers in juvenile court had. “He was unique,” Hamm told me. “It saddened me.”

The judge ordered Friedmann’s psychologist to evaluate him again. He arrived for the interview in a placid mood, carrying two books. This time, he was more candid with her, confiding that his criminal career had started before the attempted robbery at the Coin Purse. He’d been shoplifting since he was a child, he said, and saw himself as a “manipulator” and a “thrillseeker, viewing illegal activity as a challenge.”

A new personality test showed that he now barely met the threshold for schizoid personality disorder. Still, the psychologist said, “Alex is pathologically very ill,” though she didn’t specify how. She concluded, “There does not, in this examiner’s opinion, appear to be any reason to give Alex any further breaks. As a matter of fact, he would probably view this with disdain, since during the entire interview there was little indication of guilt or remorse or a sense of obligation to society.”

The judge ordered Friedmann to serve out the remainder of his probation in prison. He was transferred to a private facility in Clifton, Tennessee, operated by Corrections Corporation of America (C.C.A.). The company, which had been founded in Nashville in 1983, claimed that it could make detention facilities better for prisoners and more cost-effective for taxpayers, while enriching shareholders. The Clifton facility belied these claims. Its poorly trained officers were so terrified that they effectively ceded control to the prisoners, who were brutalizing one another.

Amid the chaos, Friedmann found a pocket of calm. An inmate named Karim Abdullah had created a study group that researched socioeconomic disparities in criminal sentencing. One day, Friedmann attended a group meeting. Abdullah recalls, “I saw this little dude, weighing about a hundred and forty-five pounds, looks like a real little nerd.” As soon as Friedmann started talking, however, Abdullah took a shine to him, and they became friends. “He was just a good, mild-mannered human being,” Abdullah told me. “Very intelligent.” Abdullah was a leader in the prison’s Muslim contingent. The group recognized Friedmann as a kindred spirit. Knowing that his small size made him easy prey, they gave him protection and included him at their table in the dining hall. Abdullah was so impressed with Friedmann’s eloquence that he enlisted him to copy-edit the study group’s newsletter.

Friedmann grew more sociable and discovered a boundless work ethic. When he wasn’t working on the newsletter, he helped put out the prison’s newspaper, and he launched his own investigative bulletin about the private-prison industry. Declining to have a TV in his cell, he read everything he could get his hands on. He especially relished Victor Frankl’s “Man’s Search for Meaning” and Aleksandr Solzhenitsyn’s “One Day in the Life of Ivan Denisovich.” (In a letter to me, Friedmann quoted “Denisovich”: “How can you expect a man who’s warm to understand a man who’s cold?”)

Surveillance footage of Friedmann shows him stashing tools and weapons throughout the jail. Video by Sam Wolson / Source videos courtesy Davidson County Sheriff’s Office

In 1994, Friedmann successfully applied to Mensa, whose members must present an I.Q. score that is at least in the ninety- eighth percentile, and he began publishing letters in that group’s newsletter. Soon he was approaching bigger publications, eager to challenge ignorant portrayals of prisoners in the press. In a letter to the Tennessean, he corrected the syndicated columnist Mike Royko’s reporting about Mumia Abu-Jamal, an activist who had been convicted, perhaps unfairly, of murdering a police officer. The Tennessean would go on to publish dozens of Friedmann’s letters. One commented on the Rwandan genocide; another argued that individuals didn’t actually have a constitutional right to bear arms. In those letters, he took a progressive tone. But in 1995, when he wrote to Science News to object to an article pondering “why lawbreakers often brandish low I.Q.s,” he sounded conservative. “Criminality is a conscious choice,” he asserted. “If not for the element of conscious choice, how could researchers explain why I—a member of Mensa with an upper-middle-class background—am serving a 20-year sentence for committing an armed robbery?”

The most introspective letter of his that I’ve read was never published. I found it in the archives of the Davidson County Criminal Court Clerk’s office. Friedmann had sent it to the judge who’d sentenced him. He thanked her for granting him probation after his first crime and for sending him to prison after the second. “Had I not been incarcerated,” he wrote, “I would have never been exposed to the lessons that I most needed to learn.”

He began writing poetry and plays. Through his writing, he appeared to develop the social conscience that his psychologist had thought he lacked. In 2021, I asked Friedmann, who was then awaiting trial for his plot at the Nashville jail, how he’d arrived at writing while incarcerated. “It’s more that writing arrived at me, as a matter of necessity,” he wrote. He had to expose the wrongs he saw around him. “I write primarily to inform, under the quaint notion that facts and accuracy matter, and to persuade. I often fail.” Nevertheless, writing gave him purpose, and, as he told me, “I’ve found that people remain hopeful so long as they have purpose.” It was also a way to control his anger. “We must all live with our faults, mistakes, poor decisions, cruelties great and small,” he wrote. “Those of us who can’t, ultimately don’t”—a reference to his suicide attempts. “I eventually came to terms with my own heart of darkness, and learned to live with it. The human condition is inherently dark, I think; to live is to suffer, due both to our actions and our inactions. Not to be too maudlin about it, though—without suffering, how would we know joy?”

Friedmann wrote a letter of apology to Mike Gambill, the manager of the Coin Purse. Friedmann told me, “If I could alter my past to avoid that traumatic and life-altering encounter with Mr. Gambill, I would. He did not deserve to be an unwilling participant in that part of my reality.” But, he added, “without that part of my past—that reality—I wouldn’t have gone on to do the things I’ve since done, learned the things I’ve learned.”

In prison, Friedmann studied civil-law casebooks, and in 1995 he sued the commissioner of the Tennessee Department of Correction in federal court, claiming that the department had violated his free speech by suppressing his correspondence with prisoner newspapers at other facilities. He investigated C.C.A. while he was in its prison in Clifton, obtaining documents and calling executives at the company’s Nashville headquarters. He eventually sued the warden and several company employees for “a continuous pattern of retaliation” for exercising his “First Amendment rights.” Friedmann was learning, as he told me, that “it’s just how the legal game is played, like chess.”

The warden Friedmann sued, Kevin Myers, told me that he found Friedmann to be “an arrogant nuisance” with no interest in perspectives other than his own. But Myers developed a grudging respect for his opponent’s tenacity: “He was very adamant about his beliefs, which I appreciate.”

In 1999, PEN America awarded Friedmann a first-place prize in its Prison Writing Contest, for his play “The Row,” about prisoners condemned to death. The same year, a few months after his thirtieth birthday, he was granted parole.

“He entered the penitentiary a lamb,” Karim Abdullah told me. “He left a lion.”

On the other side of the bars from Friedmann, Hall was asking similar questions about the cruelties of incarceration. People who work in corrections often speak of their talents as lying in one of two directions. You’re either a “security person,” most concerned with controlling inmates, or you’re a “programming person,” interested in helping them occupy their minds, perhaps to learn and grow. As a case manager in the Criminal Justice Center, Hall realized that he was a programming person. But such work was an afterthought there, so in 1991 he left to be the program director at a C.C.A. jail, in Davidson County, that was comparatively well managed. He created educational and community-interaction programs for the inmates.

Nashvillians, meanwhile, had tired of the city’s style of law enforcement. Al Gore, a liberal resident, had just become Vice-President, and the Criminal Justice Center was now seen as an embarrassing relic. In 1994, Nashville elected a new sheriff: Gayle Ray, a former English professor with no background in law enforcement. She saw inmates as citizens first, she told me, adding, “It matters to the community what condition they come out in.”

Ray credited many of her ideas to Hall, whom she hired away from C.C.A. to be her deputy. Together, they improved the Criminal Justice Center, cleaning its squalid cellblocks and firing abusive officers. In 2002, the sheriff’s office was finally released from federal oversight. Ray left the job that year, and Hall ran to replace her. At thirty-eight, he became the youngest sheriff in Davidson County history.

From his first days in office, Hall talked about replacing the jail, but he knew that it would take years to accumulate the political power to do it. He continued to improve the facility, introducing treatment programs and cutting down on overcrowding, thereby earning the praise of Nashvillians—among them Friedmann, now out of jail. He’d moved back to Nashville to become an activist and journalist. “If you want to effect change you have to do it yourself,” he told me. In a 2003 letter to the Tennessean, Friedmann wrote that “Hall should be commended for taking steps to ensure a safe and humane environment at the jail.”

Friedmann wrote as a guest columnist at the Tennessean, pushing for criminal-justice reform. State legislators invited him to testify before committee hearings, where he made for a captivating expert witness: a former prisoner so well versed in the law that his arguments had to be taken seriously.

Friedmann had begun writing for Prison Legal News while incarcerated. By the mid-two-thousands, he’d worked his way up the masthead to managing editor. He was a lifeline to writers behind bars. One young inmate, Christopher Zoukis, thinking he might have some talent as a journalist, wrote to Friedmann, who hired him. Zoukis turned out to be so gifted that they eventually became co-columnists at HuffPost. Zoukis told me, “He very much helped me turn my life around.”

Prison Legal News was published by the Human Rights Defense Center, where Friedmann became an associate director. With his help, the organization litigated against corrections authorities around the country. In Palm Beach, Florida, a case against the county sheriff helped end the practice of putting juveniles in solitary confinement. In Forrest County, Mississippi, a lawsuit allowed inmates to receive nonreligious books. Friedmann also helped Janet Wolf, his friend and fellow-activist in Nashville, with a program that brought college students to visit prisons. Wolf told me that Friedmann, as an intellectual who’d been incarcerated, “was really good at bridging both sides—both listening to the young college students who were expressing terror about going in this place but also helping the insiders find the language to tell their story.”

Friedmann had realized, as he would tell me, that “even unlikely battles can be won.” He kept up the crusade against C.C.A. that he’d begun in the Clifton prison. The company had grown into one of the largest private-prison firms in the country, with millions of dollars to spend on lawyers. Friedmann was undaunted. He wrote article after article about the company’s abuses. In 2008, he successfully sued C.C.A. in a landmark case that made private-prison companies subject to Tennessee’s Public Records Act. When President George W. Bush tapped C.C.A.’s general counsel for a federal judgeship, Friedmann built an organization to oppose the choice. After a year of his lobbying, the Senate rejected the nominee.

Most ingeniously, Friedmann bought C.C.A. stock so that he could attend shareholder meetings. During question-and-answer sessions, he waited for his turn at the microphone, and then, in his level, dispassionate voice, asked board members awkward questions, such as why they allowed so many inmate rapes in their facilities.

Rape was a special concern of Friedmann’s. After buying enough stock to allow him to propose shareholder resolutions, he drafted one requiring C.C.A. to report to shareholders the number of rapes and sexual assaults in its facilities. The company rejected the measure, dismissing Friedmann as a disgruntled ex-convict, but his campaign got widespread attention. He was profiled in Vice, Mother Jones, and the Guardian. He consulted on “Last Week Tonight with John Oliver.” Congress invited him to testify. In 2015, the staff of Bernie Sanders, who had begun campaigning for President, asked Friedmann for advice on a bill that would have banned the federal government from employing private-prison companies. The insider’s insider was ready to help.

All the while, Friedmann was pushing Davidson County to end its contract with C.C.A., which still operated the jail where Hall had worked. Many local officials now agreed with Friedmann about the company. It had rebranded itself as CoreCivic, but the ingratiating new name couldn’t hide the constant headlines about violence and corruption in its penitentiaries. Hall had grown skeptical of his former employer, but he knew that severing the contract would require long negotiations. In the meantime, he could make CoreCivic more accountable. In 2018, he convened an advisory group of local legislators, attorneys, and activists to revise the contract.

On Hall’s staff was Constance Taite, the woman who’d been Friedmann’s case manager. She’d earned a law degree and become an attorney in the sheriff’s office. Taite had also been in touch with Friedmann. “I was proud of him,” she told me. When Hall invited him to join the group, Taite welcomed him.

It gathered at Hall’s office, across from the site where the new Downtown Detention Center was being constructed. The sheriff had finally accumulated the political power to build the new jail. Between the spring of 2018 and the fall of 2019, the group held regular meetings. Hall appreciated Friedmann’s analytical rigor and calm presence. The group gave Hall a list of its recommendations—which included increasing visitation access and adding staff for programs—and most of the items were Friedmann’s. Hall’s staff came to trust Friedmann so much that, when he asked them questions about the layout of the new jail, they answered.

Street vender with huge vat labelled “A.I. SLOP.”

Hall noticed that Friedmann had fallen asleep during one meeting. He seemed overworked. His activism was rewarding but draining. In Tennessee, Friedmann told me, pursuing criminal-justice reform “has long been a task similar to the punishment inflicted on Sisyphus.” His friends knew that he struggled at times. “He carried a lot of hurt,” Wolf said. “It drove him.” Jeannie Alexander, the prison abolitionist, told me that Friedmann’s relentless pace felt like “a way to channel pain and trauma.” She and Friedmann were close: in 2019, when he married Alice, his longtime girlfriend, who was a grants analyst for the state, Alexander officiated. Yet she knew little of his past. On the rare occasions when Friedmann brought up his crimes, he spoke with vague regret. He didn’t discuss his troubled family history or his suicide attempts.

He did unburden himself to at least one friend, a man named Ferris Marone. They’d met after Friedmann was released from the prison in Clifton. Marone, a computer technician, had no connection to activism or the law, but he and Friedmann shared a history of clinical depression. He recalls talking to Friedmann about it. Marone had sought therapy and medication. Friedmann, he told me, claimed that he’d solved his affliction “by thinking through it.”

Marone admired Friedmann’s commitment to his cause. “How can we help these people?” he remembers his friend often saying. He also noticed that Friedmann was vain about his achievements. “It was important to him that others knew,” Marone told me.

Image may contain Head Person Face Photography Portrait Beard and Adult

The pair would stay up late talking at Marone’s house, and when Friedmann got really candid something irrational and thrilling in him emerged. “He had this dangerous side,” Marone told me, noting that Friedmann recounted his crimes not with regret but with glee. Marone recalled that Friedmann would claim that he’d committed crimes for which he’d never been caught, including robbing banks. Marone wondered if these stories were true. After Friedmann joined Hall’s advisory group, he and Marone discussed the new jail. Marone said, “He would say things like ‘I wonder how hard this one’s going to be to get out of.’ ”

When I asked Marone what topics most enlivened Friedmann, he instantly answered, “Guns.” Marone kept about thirty firearms at home. He knew that Friedmann, as a convicted felon, was barred from even touching a gun, and he told me that he never allowed Friedmann to handle his. But he said that he sometimes showed them to Friedmann.

Outwardly, Friedmann’s life had never been better: he had finally settled down, and he’d earned his place as one of America’s foremost criminal-justice activists. Yet Marone noticed that his friend was increasingly agitated, at times claiming that the government was after him. “He believed that, at any time, they were going to get him,” Marone told me.

Toward the end of 2019, Marone said, Friedmann started telling him, “The end is near.” Sometimes he’d say it in Latin. Growing more concerned, Marone asked Friedmann, “What’s going on with you? Are you thinking about doing something?”

Friedmann’s response was cryptic: “It’s all the stuff I’ve already done.”

The trial for the State of Tennessee v. Alexander Friedmann began on July 18, 2022. When Friedmann went into solitary confinement, two and a half years earlier, he’d looked younger than his age. During that time, he’d sued the Tennessee Department of Correction for violating his due process, and won. After twenty-one months in solitary, he was transferred to a standard cell. Still, when he entered the courtroom, he looked older than his fifty-three years. He’d dropped forty-five pounds and grown his goatee into a white beard that accentuated the gauntness of his once full face. Sitting stoop-shouldered at the defendant’s table, in a collared shirt that was too big for him, he had a spectral air.

Three weeks before the trial, he’d sent me a letter saying, “I expect it will be a trainwreck—that is, disastrous yet in a fascinating way that people can’t look away from.” He wrote, “Recently, I was asked what ‘justice’ means to me. The definition I’ve found most apt is ‘when someone gets what they deserve.’ Of course that depends on who decides what is deserved.” He’d been following the congressional hearings on the January 6th riot at the U.S. Capitol, and recalled seeing a pundit on TV: “Behind him, mounted to a wall, was a baseball bat with the word ‘Justice’ stenciled along its length. I thought that was an excellent metaphor for our criminal justice system.” It wasn’t clear whether he expected a miscarriage of justice or a harsh but deserved punishment—his pronouncements could be enigmatic. He did say that he thought a conviction was inevitable, which was reasonable, given the evidence amassed by prosecutors.

After Friedmann’s arrest, Hall’s staff had combed through two million hours of footage from the Downtown Detention Center’s six hundred cameras, compiling a reel of Friedmann’s every movement in the jail. They’d discovered that he had been infiltrating the building since at least August, 2019, when the security cameras began going online—five months before he was caught—and his familiarity with the layout in the earliest clips suggested that he’d been at it much longer.

Hall had asked the F.B.I. for help searching the jail. The F.B.I. enlisted Customs and Border Protection, which uses advanced electromagnetic scanners to search suspect vehicles. At the jail, technicians from the two agencies wired a scanner to a signal amplifier, allowing them to peer through cinder block, metal, and other materials without causing damage. The device was mounted on a trolley and rolled by every wall in the jail, looking for the “hot spots” where Friedmann had embedded weapons. By March of 2020, they’d found more than twenty. Crime-scene investigators bored holes and pulled out a succession of neat plastic packages containing razors, saw blades, handcuff keys, and security bits. The prosecutors called these “escape kits.”

Yet all the evidence amounted to little in the way of serious indictable crimes. Friedmann had stolen nothing from the jail except keys. His possession of burglary tools was a misdemeanor. The prosecutors couldn’t confidently indict him for trespassing, because when they watched the videos of his infiltrations they learned that he’d never forced his way into the jail or used a false identity. In fact, he’d often presented his own I.D. to personnel. One day, the jail’s chief of security opened a cell door for him. On another, Timothy Dial, the key-control officer, assuming that Friedmann was a laborer, helpfully led him to a stairwell, where Friedmann hid tools.

Friedmann had broken no Tennessee law by impersonating a laborer. It is a felony to introduce contraband into a penal facility, but Friedmann technically hadn’t done that, either, because the Downtown Detention Center hadn’t yet opened when he was inside it. The prosecutors considered bringing terrorism charges after Hall theorized that Friedmann had wanted to stage a violent jailbreak to make a political statement. Though this was a seductive explanation, there was no evidence that it had been Friedmann’s intent. Nor did they indict him for evidence tampering: although police had found the hand-drawn schematic of the jail that Friedmann had chewed, it wasn’t clear what, exactly, the map demonstrated, except that he knew the jail’s layout. They didn’t charge him with criminal conspiracy. Conspiracy to do what? One of the prosecutors, Amy Hunter, told me, “If I get up there and I say, ‘I think this is what he was going to do,’ I’ve already lost.”

There was one person besides Friedmann who knew about his visits to the jail: Alice, his wife. Hunter and her co-counsel, Roger Moore, had listened to the phone call that Friedmann made to Alice when he was booked. After Friedmann told her that the case could take “a good long while,” she asked, “This is one of those things with the jail project?” Friedmann’s answer is the one moment in the conversation when he hesitates or misspeaks. He knew he was being recorded, of course. “Um,” he said. “I’d rather not get over tha—into that—over the phone.”

Had Friedmann made the call before Alice became his wife, Hunter and Moore might have easily compelled her to coöperate. But Tennessee law makes it more difficult to require spouses to give evidence against each other, and the prosecutors worried that forcing Alice to testify would strike jurors as cruel.

Friedmann’s plot, extraordinary in its audacity, had the trappings of a major criminal undertaking. “It’s really rare that you have a case where somebody puts so much thought and attention into detail,” Hunter told me. Just as extraordinary was that Friedmann, who knew as much about criminal law as many criminal lawyers do, appeared to have designed the plot precisely to confound prosecutors.

There was one charge that Hunter and Moore decided they could pursue: vandalism. In Tennessee, this is typically a misdemeanor. However, if an act of vandalism causes more than two hundred and fifty thousand dollars in damage, it is a Class A felony. And, if that damage is caused by someone with a serious criminal record, it can bring up to sixty years in prison.

“You may think that what I’m telling you is a made-up story from a Hollywood movie,” Hunter told the jury in her opening statement. It was a fitting introduction to a four-day trial that came to resemble an endless heist film. Although jail officials and police officers testified, the most crucial evidence was presented on large monitors. For hours, the jury watched surveillance footage of Friedmann going about his “work.” One juror dozed off, but, as Moore told me, the overkill was intentional, to underscore that “this was a concerted effort.”

Moore told the jurors that Friedmann’s attack on the jail was an attack on Nashville. “Our jail,” he called it. “The baby of the sheriff, and the people that he trusts and works with. They were so proud of that building, and somebody they let into their meetings—who had a place at the table—did this to them, and to the people of Davidson County.”

Woman walks into surprise party planned by current lover and guests that are ex lovers.

I attended the trial and sat near the defendant’s table so that I could watch Friedmann’s reactions. If only he’d exhibited any. I’ve been in many courtrooms, but I’ve never seen a defendant, or possibly anyone anywhere, sit so inertly for so long. He took notes and occasionally whispered to his lawyers, but otherwise was lithic in his stillness. I saw him express something like emotion only once, when Hall testified.

“Do you know Alexander Friedmann?” Moore asked him.

“I do,” Hall said.

“Could you indicate which person he is?” Moore asked.

With this, Friedmann smirked at Hall and gave a quick wave of the hand. I couldn’t tell if he was awkwardly attempting friendliness, or taunting the sheriff, or both. Hall had said that Friedmann should be “sent away forever,” and Friedmann had accused Hall of poisoning the jury pool. And yet there Friedmann was, waving at his antagonist. It was such an eerie moment that Hall commented on it: “Yeah, he’s waving at me, right there.”

Friedmann didn’t testify. Though he was articulate and a lauded humanitarian, his stiff demeanor was off-putting, and, as he later told me, “most criminals aren’t very sympathetic.” But that isn’t why Friedmann decided not to take the stand. He felt that he had no way of disproving the charge. Moreover, he knew that the prosecutors might ask him certain questions that, if answered truthfully, could help insure his own conviction.

In February, 2020, after Friedmann turned himself in, Hall got a call from a Nashville attorney who had seen news of the case and recognized Friedmann. He shared his office with a notary public who’d notarized documents for Friedmann. Copies of the documents were in the office. Robert Anderson, the lead detective on the case, got the copies, one of which was a letter that Friedmann had addressed to a relative of his by marriage, Greg Hall (no relation to the sheriff), a handyman who lived in a Nashville apartment complex where Friedmann had once resided.

Anderson went to see Greg Hall, who had a workshop in the complex’s basement, where he’d built Friedmann a storage space. Friedmann had told him it was for legal documents. Anderson noticed that the storage space was made of cinder-block walls, as the Downtown Detention Center was. Greg Hall told Anderson that Friedmann had watched intently as he’d built it. He’d shown Friedmann how to cut into cinder blocks with an angle grinder. When Anderson examined the mortar joints, just as he’d done in the jail, he saw blemishes and discolorations. Hall said that he hadn’t made them. He also said that, on the day Friedmann surrendered, he had seen him take away several plastic storage crates in a U-Haul truck.

Anderson traced the truck to the address of Friedmann’s friend Ferris Marone. The storage crates were in the house. One was labelled “Legal stuff.” Inside the crates, Anderson found not documents but six assault rifles; two shotguns; fourteen handguns; body armor; a 37-mm. launcher that could fire tear gas, flares, or smoke cannisters; and thousands of rounds of ammunition. Friedmann, as a convicted felon, wasn’t allowed to have any of it. Federal prosecutors indicted him on firearms charges. That case was being litigated simultaneously with the state’s vandalism case.

Hunter and Moore called Greg Hall to testify, and showed the jury photographs of the storage space. But, because the arsenal was irrelevant to the vandalism charge, they didn’t mention it, or Friedmann’s federal case, to the jury. Had Friedmann testified, they might have at least hinted at those things. And the arsenal was only the latest example of his infatuation with secreting away weaponry.

In 1991, after the Kroger incident, police had found a paper on which Friedmann had listed dozens of venders who sold military-grade firearms and equipment. Friedmann’s psychologist, in her first evaluation of him, had included this stipulation in the terms of his parole: “Under no circumstances would Alex be allowed to possess weapons or materials construed to have the potential to be assembled into weapons.” In her second evaluation, she wrote, “He claims to view himself as a military buff who wants to know about the latest weapon technology.”

Instead of revealing any of this to the jury, Hunter and Moore tallied Friedmann’s vandalism. They calculated that, between the expenses of replacing all the locks and keys in the jail, paying overtime to staff who reviewed footage, and renting jail space (from C.C.A.) for inmates who couldn’t move in because of the investigation, Friedmann had cost the sheriff’s office the equivalent of $1.5 million—six times the figure needed to convict.

After deliberating for about an hour, the jury found Friedmann guilty, as he’d predicted.

At the sentencing hearing, in October, 2022, no jurors were present. In this forum, the prosecutors could present more evidence to the judge. When they showed him images of Friedmann’s personal arsenal, the judge, dismayed, remarked that it was “enough to start a war.”

After he’d been convicted, Friedmann had written to me to say that “my attorneys will be filing various documents in advance of the sentencing hearing that you (and others) should find interesting.” This was an understatement. The filing included a letter to the judge from Friedmann which contained the first public explanation of his plot. In the letter, he recounted being brought to the Criminal Justice Center, in 1987, when he had been eighteen and small, with his hand in a cast. “I was cornered in a cell by three inmates,” he wrote. “They threatened me with a shank, grabbed and twisted my injured hand, and forced me face down on a bunk. I was unable to defend myself and two of them raped me. I told an officer what had happened and asked for help. He said I needed to fight back, then walked away. The next day I was raped again. It was the most traumatic, painful and humiliating experience in my life.”

In 2016, when the demolition of the Criminal Justice Center was about to begin, Friedmann asked the sheriff’s office for a tour, so that he could photograph the old jail for a website. “But I also had another goal: to visit the cell where I had been raped, to obtain closure.” Instead, he broke down, and afterward he was beset by nightmares and panic attacks. “I resolved that should I ever be jailed again and subjected to the same sexual abuse, I would have the resources to escape or defend myself. And since the new jail was being built, I had a one-time opportunity to accomplish that by concealing escape tools and weapons in the facility as a contingency plan. And that’s what I did.” He’d put them in all of the jail’s fourteen cell blocks because, in the event that he was imprisoned, he couldn’t know where he’d be held. He described the process as strangely therapeutic: “The further I progressed with my contingency plan, the more the effects of that trauma diminished.” He concluded, “My actions were not rational, but responses to extreme emotional trauma often are not rational.” He quoted Solzhenitsyn, as he’d done in the letter to me—“How can you expect a man who’s warm to understand a man who’s cold?”—and noted that he should have received therapy long ago. The letter concluded with the Latin phrase fiat justitia—let justice be done.

Sheriff Hall testified again. His sense of betrayal had not subsided. “As a person who’s spent thirty-five years believing the criminal-justice system should provide better opportunities and second chances, I stand before the court asking for neither,” he said. Describing the danger Friedmann had put his staff in, he choked up. “Friedmann has had second chances and deserves no more.”

Friedmann decided to speak at his sentencing hearing. He apologized to Hall and to “the prison-reform community, whom I let down.” He said, “While my life is effectively over, the need for meaningful reform remains.”

The judge acknowledged the need for prison reform but appeared unmoved by Friedmann’s account of rape. He said, “I just don’t believe it.” As he read out the sentence—forty years—Friedmann’s face betrayed no emotion.

Afterward, in a letter to me, Friedmann said, “I had committed the unpardonable sin: Endangering law enforcement officers.” He went on, “If I recall correctly, around 10 people are killed by the police for every officer who dies in the line of duty . . . a disquieting ratio.”

When I first wrote to Friedmann, in 2021, before the trial, he replied at once, though only to say that he was disinclined to meet. He wrote, “I’m not Jack Abbott and you’re not Norman Mailer,” a quip I enjoyed, as I suspect he knew I might, not least for its paradoxical mixture of humility and vanity. The murderer and writer Jack Abbott was in prison when Mailer befriended him, and went on to kill again after Mailer lobbied for his release. Friedmann, as a journalist and a self-taught legal expert, was too savvy to discuss the details of his pending case with a reporter. “I expect the article you write about me will also be fairly one-sided, though due to no fault of yours,” he said. “Hopefully you won’t trot out that old canard, that it will give me an opportunity to tell my side. Rather, it would help you tell your side, or at best your version of my side.”

Though he wasn’t willing to let me visit, we continued to exchange letters. He generally kept me at a remove with a formal tone. “I’m fairly proud of my past accomplishments in the vastly underappreciated area of criminal justice reform,” he told me, adding, “To write about me is to write about my work.” Indeed, he became effusive only when recounting those accomplishments. But his letters were also lively, wry, and candid when he wrote about matters that didn’t bear directly on his case: books, the broader criminal-justice system, politics, philosophy, vegetarian junk food, the inaccuracy of police dramas.

He described the indignities of incarceration with mordant wit. He’d recently been quarantined in the infirmary, and recalled, “I met a condemned prisoner suffering from cancer, partially paralyzed and confined to a wheelchair, who was receiving treatment before being returned to death row. God forbid the hangman be cheated.” Of his legal representation, he remarked, “I’ll just note there is a lack of urgency among attorneys—who are not held in a solitary confinement cell the size of an average parking space.” Before I learned that inmates in Tennessee can receive only paperback books, I mailed Friedmann some hardcovers. They were confiscated, but, he reassured me, “The mailroom was kind enough to let me have them after tearing the covers off.”

One matter that Friedmann didn’t discuss with me was the story of his rape, which was certainly plausible. Sexual assault is common in American penitentiaries. According to the National Prison Rape Statistics Program, a Department of Justice initiative, about four per cent of American adult inmates report being sexually abused, but experts on the subject believe that the rate is probably higher.

Friedmann didn’t mention the rape to any of the activists I interviewed, or to Taite, his case manager at the Criminal Justice Center. In his advocacy work, he often invoked his own prison experiences, but he never mentioned being raped. Then again, according to his lawyer, he never even told his wife. The one person I spoke to who did get an inkling was his friend Ferris Marone. Friedmann, he said, told him about being abused in prison. He didn’t mention rape, Marone told me, but “sometimes he would slip up and say it was sexual abuse.”

Two tumbleweeds rolling past an old west general store.

At least one fact contradicts Friedmann’s account in court. Friedmann’s visit to the jail cell where he was assaulted—the supposed inspiration for his plot—was in 2016. But a check that he wrote to Greg Hall, the handyman, for the construction of his storage place, is dated August 15, 2015—just four months after Sheriff Hall first announced plans for a new Nashville jail.

At the sentencing hearing, Hall said that Friedmann’s “sensational story” was “just another trick of this narcissist,” which is as much mental illness as the sheriff is willing to grant him. Hall knows only too well that a third of arrestees in Nashville are mentally unwell—it’s why he put a behavioral-care clinic in his jail. But, when I suggested to him that, had such a clinic existed in 1987, Friedmann might have stopped committing crimes, he disagreed. Friedmann’s pathology was “scary because it’s not rehabilitatable,” he said.

Had Friedmann infiltrated a CoreCivic prison, Hall might have understood the motivation; he sympathizes with Friedmann’s grudge against the company. But he felt that Friedmann was ultimately as inexplicable as Charles Manson—there was no “why” behind his actions. Hall told me, “There’s a handful of people in my lifetime I can say that about.” Although Hall believes that his job requires forgiveness, he can’t forgive Friedmann. “There’s just evil there. I know that.”

Matt Foster, the F.B.I. agent on the Friedmann case, has retired from the Bureau. During his twenty-six-year career, he interviewed bank robbers, escape artists, jihadists. Usually, he could boil their motivations down to profit, ideology, or revenge. Only in a very few cases did his subjects defy explanation. Friedmann is among them. “There’s such a complex mixture of trauma, grudge, vengeance—and something else that we can’t even articulate,” Foster said. “There are some minds that you just have to accept you are never going to get.”

Friedmann’s parents, Victor and Toni Jo, feel similarly. The couple, who are now living in North Carolina, declined to be interviewed, but Victor did say, “We’ve been asking ourselves for years why he’s the way he is, and no one’s been able to answer. And don’t think you’ll get the answer.” In 2022, Victor self-published a book about his family. It doesn’t mention Alexander.

Marone believes that Friedmann’s plot was, ultimately, an elaborate way to get himself back in prison. He theorizes that Friedmann had spent so many of his formative years incarcerated that, even after two decades of freedom—and after all his professional success—he craved confinement. In some primal part of his brain that he couldn’t reason his way out of, he longed to be a real insider again. Psychologists call this “institutionalization.” Marone said, “He mentioned once that he was ready to go back. . . . He knew about prison. He knew how things functioned.”

There is evidence to support this theory. In 1992, when Friedmann’s psychologist conducted her second evaluation of him, he’d been in jail for nearly a year. She observed that he seemed happier than when he’d been free. “He is making a good adjustment to prison life,” she wrote. “He seems to be at home in a comfortable environment.”

She also noted that, though Friedmann was reading novels in jail, the book he was studying most closely was “Games People Play,” by Eric Berne, a Canadian clinician who developed a psychiatric theory he called “transactional analysis.” Berne argues that all social interactions are a type of psychological game—including crime. There are “two distinctive types of habitual criminals,” Berne writes. “Those who are in crime primarily for profit, and those who are in it primarily for the game.” Criminals in it for the game relish a “battle of wits” but often wind up in prison, because of a mixture of guilt, shame, and vanity. In fact, they may want to be caught, because “being found is the necessary payoff,” the due recognition of their daring. The book, a best-seller during the sixties, is an early and not overly convincing example of pop psychology. In his first letter to me, Friedmann urged me “not to hypothesize” about his personality. Still, his attachment to the book struck me as telling.

Craig Proctor, the childhood friend who played Dungeons & Dragons with him, told me that Friedmann once showed him architectural floor plans for a citadel that Friedmann’s thief-rogue avatar would oversee. Proctor was amazed by their artistry and detail. When he learned of Friedmann’s plot, the first thing he thought of was that citadel. Friedmann’s infatuation with the game had continued after he moved to Nashville, becoming so intense that his psychologist stipulated in the terms of his parole that, along with being kept from weapons, he be prevented from playing fantasy games such as D. & D.

At times, in Friedmann’s letters to me, he seemed to be playing a game. He wouldn’t discuss his case, but he dropped coy hints. Once, he sent me an old article about a 1982 case in which a prisoner smuggled a gun into the Brushy Mountain State Penitentiary, west of Knoxville, and went on a shooting spree. Friedmann didn’t explain why he sent it. But a year later, in his letter to the judge, he cited the Brushy Mountain incident as his inspiration to smuggle guns into the jail.

He may have wanted to engage Sheriff Hall in a battle of wits, leaving a trail of clues behind for a cunning opponent. He knew he was being recorded by the jail’s cameras, and he always wore the telltale dust mask. He surely noticed that the circular key ring he left in the key-control room was unlike every other key ring in the jail. Still, for days, he let it hang there, its lock cracked, instead of replacing it. By having letters notarized, he left a paper trail that led to his arsenal. Clues were still turning up long after the Downtown Detention Center opened, in May, 2020. More than three years later, Hall’s staff found a correctional officer’s uniform that Friedmann had stowed in the jail’s ductwork.

Although crime is down in Nashville, the Downtown Detention Center has been plagued by overcrowding. Last year, Hall announced that he wants to build another jail. When I last visited him in Nashville, there was a new addition to his headquarters: a little museum chronicling the history of the Davidson County Sheriff’s Office and its most notorious inmates. There are enlarged mug shots of Paul Dennis Reid, Jr., better known as the Fast Food Killer, who was sentenced to death after murdering seven people during a string of robberies at chain restaurants, and of Bruce Mendenhall, a.k.a. the Truck Stop Killer, who is serving multiple life terms. In pride of place is an exhibit titled “Alexander Friedmann’s Plot Against the Downtown Detention Center.” The crime is memorialized with a dust mask, one of the recovered revolvers, and the circular key ring. A plaque reads: “It all started with a set of keys. . . .”

Friedmann began appealing his conviction in 2023. Last summer, the appeal was denied. In December, the Tennessee Supreme Court declined to review the case. Friedmann is now in the Bledsoe County Correctional Complex, in Pikeville, where he is still writing. He has been contributing to the online magazine of the Prison Journalism Project, covering minor injustices, such as the comparatively high cost that his Muslim prisonmates have to pay for Qurans. He has not lost his sense of humor. Recently, he wrote an essay called “The Art of the Prison Fart.” In 2022, his play “Twenty Years in Solitary” earned him another first-place award from PEN America.

In a letter he sent me after his conviction, Friedmann included a poem he’d composed, or, rather, re-composed. It was based on “I Have a Rendezvous with Death,” by the American poet Alan Seeger, who died at the Somme while fighting with the French Foreign Legion. Friedmann renamed it “I Have a Rendezvous with Fate (with gratitude & apologies to Alan Seeger).” He wrote: “Confined in a dark and barren cell / resigned to my own private hell / which nurtures both despair and hate / I have a rendezvous with fate / . . . So that when I draw my final breath / I’ll embrace the soft release of death.”

In his last letter, Friedmann said that he no longer wanted to communicate with me. He signed off with a quote, in French, from Rabelais. It is believed to have been the writer’s dying words: “Tirez le rideau; la farce est jouée.”

Drop the curtain; the farce is over. ♦

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