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The first time Larry Caldwell attempted a stickup, no one took him seriously. It was a Friday morning in late May 1971, and Caldwell and his partner, Eros Timm, entered a bank in downtown Charlottesville, Va. The robbers hadn’t cased the place beforehand. In fact, they had hardly ever set foot in the bank until the moment they opened the door to rob it. But if they hadn’t done much in the way of planning, they had at least put serious thought into their disguises. They wore sunglasses, blazers, and ties, and they tucked their long hair into short-haired wigs. As they walked in, Caldwell pulled his sawed-off shotgun from under his jacket, fired a shot at the ceiling, and shouted, “This is a holdup.”

The manager of the bank, busy with another customer, laughed and told Caldwell to get in line. The customer turned in his seat and told Caldwell he was too well-dressed to be a bank robber. “They were telling one-liners,” Caldwell recalls.

As the manager later explained, college kids were pulling pranks all the time at the bank, and he assumed that Caldwell’s blast was a blank. Not until some moments later, when Caldwell came back at him with a revolver, and bullets could be seen in the chamber, did the manager drop to the floor. And still the robbers couldn’t scare up the cash. “I don’t have any money,” the teller told Timm.

Timm and Caldwell had given themselves only a few minutes to do the job, and by now they sensed that their time was up. The would-be stickup men fled the bank empty-handed and drove the 20 miles back to the farm where Caldwell was staying. Caldwell can’t recall clearly what happened next, but he says they probably buried their humiliation in his stash of weed.

Caldwell lived in the rented farmhouse with four other hippies. Timm and Timm’s girlfriend, Heidi Ann Fletcher, who lived together in Cleveland Park, were part of the same circle of friends, and they frequently drove the two hours down from Washington to visit. Caldwell, who was 25, was a classically trained clarinetist who had come to D.C. a couple of years before to study under the principal clarinetist of the National Symphony Orchestra. Caldwell had then given up music in favor of small-time drug dealing and moved to the country. Timm, who was 22, was frequently out of work and living off Fletcher, a 21-year-old legal secretary. As headlines would later note, Fletcher was the daughter of Thomas W. Fletcher, who until recently had been deputy mayor of the District of Columbia.

Their aspirations were loftier than mere riches. They would lounge around the farmhouse living room and freely rant about the impending revolution. “There was a saying: ‘Kill a commie for Christ,’” says Caldwell. “So we said, ‘Off a pig for Krishna.’” Their goal was as faddish as their politics: They wanted to raise $50,000 so they could purchase a farm for themselves. A morally tolerable way to do that, they decided, was to rob banks.

For the second heist attempt, they made some adjustments. Fletcher, left out of the Charlottesville job, would be the driver of the getaway vehicle. And this time they decided to rob banks in D.C., where they figured crime was the accustomed way of life and tellers would be trained to offer up the money on demand. Indeed, Washington was experiencing an epidemic that year: By the end of May, District police had already recorded 50 bank holdups, compared with 29 in all of 1970.

On the Monday following the Friday failure in Virginia, the three conspirators circled around Northwest D.C. in Timm’s old Chevy van. They settled more or less at random on a savings and loan on Massachusetts Avenue. Caldwell and Timm were in and out in minutes, and they made off with more than $4,000.

Believing they’d discovered a successful formula, they set out again the next morning, cruising around Northwest D.C. until they found another place with a vulnerable vibe. They hit a small branch of the National Permanent Federal Savings and Loan Association, located in a MacArthur Boulevard shopping strip. At first, the job went smoothly and quickly enough. But because they hadn’t cased the bank beforehand, they didn’t know that two uniformed police officers were staking out the place that day. The cops burst out of a rear office soon after Timm and Caldwell walked out the door.

Several flights of steps led from the parking lot to a dead-end street above and behind the shopping strip, where Fletcher sat behind the wheel of the getaway van. As Caldwell and Timm headed for the stairs, one of the policemen, William Sigmon, screamed, “Halt!” and a shootout ensued. The robbers took positions near the stairway. Sigmon advanced to a spot below a concrete embankment next to the stairs. Timm walked slowly over, reached down through the handrail, and shot Sigmon in the back. Caldwell and Timm reached the top of the stairs and jumped in the van, and Fletcher drove them to the Bethesda home of Timm’s parents.

Timm had sustained wounds to his side and leg, and he was breathing heavily. Instead of holing up for the night in Bethesda, Caldwell decided he was going to take Timm to some medical students in Charlottesville for treatment. Seventy minutes after the shootout, they headed for Virginia.

Fletcher drove the van down busy Connecticut Avenue and into the middle of a dense manhunt. Within minutes, a cop pulled them over at the Van Ness Shopping Center, and as the three were handcuffed, Caldwell learned that they had murdered a police officer.

For the last time in his life, Caldwell hadn’t thought something all the way through.

Last December, Caldwell was released from the D.C. Jail. He had been locked up for almost 33 years, minus 14 months in the ’80s following an escape. When he emerged from the jail exit, at around 6 o’clock in the evening, a small crowd of staffers were gathered to watch him leave. During his incarceration, Caldwell had acquired an impressive store of documentation, and behind him in the hall were about a dozen boxes of legal filings. One of the correctional officers gave Caldwell a hand truck, and he and his attorney loaded them into the trunk of the car Caldwell’s attorney had parked in the lot.

From the beginning, Caldwell was one of the D.C. system’s more infamous figures. Memories of the cop killing and the sensational trial that followed never quite faded away. And he built on his notoriety with his escape activities. At the same time, he developed into possibly the most skilled inmate litigant in D.C. custody.

Caldwell walked out a relatively wealthy man. In recent years, he had won more than $200,000 in settlements and judgments based on his mistreatment in D.C. facilities. But upon leaving the jail, he showed little sign of relief. He would no longer have to file suit to get Motrin for a root canal, and he was about to have his first meal on a tablecloth in 20 years, yet he was still hung up about the few weeks he would have to sleep at a local halfway house. “It just meant a new system to beat,” says Jason Wallach, Caldwell’s attorney.

In January, Caldwell moved from the halfway house to a carpeted apartment near Catholic University. He stocked it with IKEA furniture, about a dozen pints of Häagen-Dazs and Ben and Jerry’s ice cream, and a full complement of fine liquor, which he put on display on tall shelves. Nearly a year later, the décor hasn’t changed much. There are no photos or posters hanging on the walls. The one picture is a charcoal sketch perched on a shelf above his computer. The artist is a friend from jail whom Caldwell helped file a legal complaint. Caldwell’s bed is a simple air mattress in his weight room. He reserves the master bedroom for his one true extravagance: a $12,000 entertainment system from Myer-Emco.

Caldwell, now 58, is tall—6-foot-6—and thin, with a slightly slouching frame. He has pale skin, a wide, flat face, and a trimmed white beard. He kept his hair long during his last years in confinement—he didn’t trust the hygiene of D.C. Jail barbers—but he cut it when he got out. The short gray locks sprouting from his widow’s peak flop onto his forehead, like the movie image of Depression-era delinquency. His eyes—shielded by large, owlish glasses—are less sinister. One eye is clouded with glaucoma; the lid of the other droops. A pink crater marks the spot on the tip of his nose where jail officials neglected to treat a cancerous lesion. During a series of interviews in his living room, Caldwell sits in a lounge chair dressed in his customary ensemble of sweat pants and an undershirt. Underneath a coffee table stacked with classical concert schedules, he has placed a brown paper bag, and as he speaks he picks lint off his sweat pants and deposits it in the bag.

Caldwell says that in prison he snuffed out the sloppiness that had gotten him there. But his fastidious personality is not something he developed behind bars. Unlike many inmates, he has always had an acute sense of order. “I had been a professional musician and very disciplined in other areas of my life,” he says. “Most people who are incarcerated don’t have that discipline.”

Prison gradually honed that discipline—not by reforming him but by challenging him. If it was a prison’s job to keep him in, it was his job to get out.

Caldwell was born in Las Vegas in 1946. His mother was a waitress; his father was a card dealer who died when Caldwell was 2. A drunk, unemployed stepfather beat both Caldwell and his mother, but Caldwell says the tales of an awful upbringing told to his psychiatric evaluators 30 years ago were exaggerations intended to bolster his insanity defense. Caldwell’s older brother, David Caldwell, says the two boys were left to themselves most of the time—abuse by neglect.

David says that Caldwell—who went by Danny, his middle name, for most of his life—was “bullheaded” from an early age. He was the only kid in a local occult group, and even as he got older he steadfastly believed that aliens were using the moon as a staging base for visits to Earth.

The clarinet, which Caldwell picked up in junior high, focused his days like nothing else. While his single-minded dedication to the instrument was clearly a form of escape, says Caldwell, he also simply liked classical music.

After graduating from high school, Caldwell enrolled at the prestigious music program at Indiana University. He never assimilated into college life; when he wasn’t practicing his clarinet, he might go to a movie alone. After a year in Bloomington, he won a scholarship to the Cleveland Institute of Music, where he was under the tutelage of musicians of the world-renowned Cleveland Orchestra. Several professors there didn’t like Caldwell, who was considered an antisocial contrarian.

“I just know it was very difficult for Dan to accept that people knew more than he did,” says Rick Solis, a close friend from Las Vegas, who joined Caldwell at the institute. He says Caldwell was an expressive player whose main weakness was technique. “When things didn’t go his way, he’d act in a pretty weird way.” Solis, who now plays French horn for the Cleveland Orchestra, remembers a student performance of An American in Paris in which Caldwell squeaked a few notes. Caldwell threw himself down a flight of stairs in self-disgust, says Solis. (Caldwell says he doesn’t recall the episode.)

Caldwell flunked a course in pedagogy, and he lost his scholarship. Over the next year, he worked in the classical department of a local record store and performed some gigs with the Akron Symphony. Feeling that he effectively had been shut out of the Cleveland-area music scene, he made plans to go to Washington to study under the NSO’s Buddy Wright. Before he was to leave for D.C., an FBI agent informed Caldwell that he had to respond to the draft notice he’d been avoiding. Caldwell ignored the warning, and in D.C. he went by an alias to keep the feds off his tail.

His semi-fugitive status checked his ambition. “I was one of the best young clarinetists in the country and I couldn’t get a fucking job,” he says. “Lawrence Caldwell the clarinetist is being sought by the FBI. Where was I going to go for work?”

As personal disappointments gelled with his emerging radicalism, the clarinet no longer seemed important. He accidentally left his instruments behind in storage when he moved out to rural Virginia, and he never picked up the clarinet again. Prison wouldn’t allow it, even if he wanted to.

When Caldwell and Timm’s trial began, in February 1972, it was one of the highest-profile criminal proceedings in years. The robbers were white, they were hippies, Fletcher was the daughter of a prominent Washington figure, and a cop was dead. Rarely does such rich material come together in one courtroom, and reporters gave the story the shorthand title of “the Heidi Trial.”

Fletcher, though, would never go before a jury. A few months after her arrest, she was released into the custody of a family friend, the city’s planning director, and while prosecutors assembled their case, Fletcher put in time as a secretary at an advertising agency. After she pleaded guilty in December, a judge invoked one of the more lenient options available to youthful offenders and sentenced Fletcher to a maximum of nine years in a prison in California, where her parents lived. She was released four years later.

In the eyes of the prosecution and the press, the timid Fletcher never seemed a credible criminal. Nor did the baby-faced Timm. The mastermind was clearly Caldwell. He was too canny and intense—and the others too evidently passive—for Caldwell not to have been the Manson-like figure who led the other two astray.

“There was no question that he had a hypnotic hold on Eros Timm and Heidi Fletcher, neither of whom had the manic streak that this man had,” says Bob Levey, who covered the trial for the Washington Post. Timm and Fletcher “were just ’70s kids out to have a good time.”

Early on, Caldwell asked one of his attorneys what his chances were, and the attorney replied with some simple advice. “He said, ‘Escape as soon as possible,’” Caldwell recalls. And so, in a first indication of the kind of mental focus he would later train on escape, Caldwell devised his own legal tactic: He would carefully and methodically go insane.

Beginning in the summer of 1971, Caldwell stopped eating. He relaxed his muscles, his body went completely limp, and he used his bed as a toilet. For three months, whenever Caldwell appeared at a pretrial hearing, he would sit lifeless in a wheelchair, with his head hanging down over his chest and slobber dribbling down his chin. He was force-fed through a tube. One time nurses shot him up with adrenaline to keep him alive.

But at this novice stage in his criminal development, Caldwell’s endurance had limits. About a month before the trial commenced, he went on hiatus from his performance, and the courtroom suspense slackened as witness after witness nailed the suspects with their testimony.

About midway through the trial, the defense called Fletcher to the stand in the hopes that she might speak kindly on behalf of her co-conspirators. “The jury would have believed everything she said,” says Caldwell. Instead, she took the Fifth Amendment.

Caldwell’s insanity ruse was completely deflated when, on the 16th day of the trial, an inmate who worked in the jail medical ward testified that when they were alone together Caldwell wasn’t so crazy. Caldwell would write letters, he had poked a hole in the feeding tube so that the liquid would be diverted into his mouth, and he had even complained about the lack of vegetarian options on the jail’s menu.

Back at the jail a few hours after the inmate’s testimony, Caldwell staged a suicide gesture, scraping his arms with the broken glass of his spectacles. The next day he was rolled into the courtroom, once again in his rag-doll pose, with his arms bound to the sides of the wheelchair with bedsheets.

When, a few days later, the jury foreman announced guilty verdicts for murder and armed robbery, Timm laughed. Caldwell, who still placed hope in an appeal, stayed in character, limp in his wheelchair, his head sunk, as if he hadn’t heard.

Cop-killer was a good rap to have in prison, and it earned Caldwell some instant respect. But he wasn’t concerned about getting along. He was concerned about getting out. He would later feel remorse for the shooting, but he didn’t feel he could do the time. “If prison is the problem,” he says, “then getting out of prison was the solution to the problem, however that could be achieved.”

His first efforts were amateur in comparison with the work that would come later. In Charlottesville for his trial for the attempted robbery there, he stepped out of the second-story window of his holding room and was instantly apprehended. In prison at Terre Haute, Ind., in 1973, he constructed a crude mannequin to take his place in bed as he attempted to find his way out of the prison yard; he was caught because a correctional officer came by his cell to deliver a letter. (Maybe it was just bad luck. Caldwell rarely got letters.) Later in 1973, while in transit to Leavenworth, he scuffled over a gun with his police escort. It was the last straw. He was shipped to Marion.

The feds opened Marion in 1963, when Alcatraz had outlived its usefulness. Located in the farmlands of southern Illinois, it was the highest-security facility in the system, a repository for several hundred inmates tagged as extremely dangerous, escape risks, or both.

The harsher conditions only increased Caldwell’s desire to escape. Escape planning wasn’t only a physical necessity, but a mental one. Thinking about it kept him “future-oriented,” he says.

At first, he left the calculations to others. He wasn’t yet familiar enough with the facility to venture out on his own, and he was satisfied going along with whatever plot was already in the works. But most of the time, Caldwell discovered, escape plots were more talk than action. “A lot of people who are in this don’t really ever want to escape,” says Caldwell, “They just want people to know, ‘Oh, there’s an escaper,’ and when I determined that was the case, I decided that most people weren’t serious. They weren’t disciplined, they weren’t in shape, and they sure as hell weren’t mentally prepared.” So he decided to go it alone.

He began to think of his long sentence as a psychological advantage. It motivated him to take risks, and it gave him the time he needed to construct his elaborate schemes. His first solo attempt at Marion required about a year of preparation. His plan revolved around a window in the officers’ mess hall.

At the time, Caldwell worked in the kitchen. Kitchen duty was a prized prison gig because of the access to free food. It also offered hours of unsupervised free time in the mess. For months, Caldwell buffed the floors, and on his breaks he went to work on the steel bars of a window frame with a homemade hacksaw. “I did a little bit of work for them, but I did most of the work for me,” he says. “I thought that was fair.”

Acquiring blades good enough to cut steel probably ranks as one of Caldwell’s more impressive achievements at Marion. Caldwell took part in several prisoner-outreach programs. One reason, he says, was to keep in practice speaking like a well-adjusted human being; another was to put him in contact with people who could help him get out. College kids from the nearby Carbondale campus of Southern Illinois University took part in one of the programs, and Caldwell, the long-haired inmate who talked feverishly about revolution, made an impression on a sympathetic student who was willing to smuggle him industrial hacksaw rods.

By spring of 1976, everything was set. The window bars, which he had been sawing at whenever he could, required just one last push. Now he needed only to wait until the weather turned bad to hide his escape. But then the plot was put on indefinite hold. A run-in with a correctional officer in the yard—he accused Caldwell of smoking pot—got him kicked out of the kitchen. It would be months before he would get his job back. In the meantime, he endured the wait by exulting in his future success. “You can’t imagine knowing you have an actual exit they don’t know about from the most maximum-security prison in the country,” he says. “This gives you a real joy, joie de vivre. At least to that extent, I had beaten them.”

For his escape, Caldwell would take with him a warm army-surplus jacket, a pair of wire cutters for the fence, and tarot cards. Having learned from the shortsighted mistakes of others, Caldwell had also stockpiled food, maps of the surrounding area, and a radio so he could tune in to the news. He grew impatient waiting for bad weather that never came, and decided to escape on New Year’s Day, when the showing of a double feature would delay the evening inmate count for an hour or so and give him more time to get out of the building. He also figured the guards would be hung over and less alert.

That night, Caldwell hid under a counter in the kitchen as the room was being locked up. He pushed out the window, stepped into the courtyard, and then used the window frame to climb up to the roof. Crossing the roof, he crawled down to the kitchen loading dock.

The dock was about 10 yards from the inner fence. A light dusting of snow covered the grass in between. Caldwell figures that his dark jacket stood out from the snow. He wishes in retrospect that he had taken along white clothing or just made a run for it. Instead, he crawled. According to an official report of the incident, the officer manning the tower spotted him and fired his shotgun three times from a range of 125 yards, catching Caldwell in the right thigh with a single pellet. Caldwell surrendered.

The incident earned Caldwell a six-month stay in Marion’s control unit, where he was confined to his cell, alone, for 23 hours a day. But Caldwell was just getting started. His attempted breakout had earned him a reputation among other escape artists, who were eager to share their skills with the guy who had managed to get the blades. Many of his new associates happened to be experienced bank robbers, a demographic that represented some of the prison system’s brighter minds. A couple, says Caldwell, were outright criminal geniuses, including a safecracker who could memorize the pattern of a key by simply looking at it a few times. They all possessed more criminal knowledge than Caldwell, and they instilled in him the professional notion that if you were in a position to help another con in the group, you were duty-bound to do so.

For Caldwell’s second attempt, in February 1978, he enlisted several from this clique as collaborators. It wasn’t just their skills that were useful. The more bodies that got over the fence and then scattered in opposite directions, the harder it would be to find any one of them.

With plenty of his contraband blades still stashed around the prison, Caldwell’s plan relied on the same hacksaw strategy as the year before. But this exit would be tougher. He no longer had easy access to the kitchen or officers’ mess. Instead, he planned to get through the window of the prison psychiatrist’s office. Two locked doors separated an inmate lounge from the window.

After several weeks of labor by his safecracker buddy, the keys were done, and now Caldwell slipped into the office whenever possible to saw away at the frame of the window. But one day his lookouts in the lounge—known as “jiggers”—failed to notify Caldwell when a correctional officer patrolling outside drifted by the window. The officer heard the sound of the sawing. Caught again, Caldwell was sent back to the control unit—and the drawing board—for another six months.

In February 1979, almost exactly a year after his second attempt, Caldwell tried a third time, again by similar methods. On this attempt, Caldwell was joined in the escape by two other bank robbers, Al Garza and Skip Zumberge. Garza sought him out for the job.

“Danny is relentless when it comes to something like that,” says Garza, who is now doing his time in a federal prison at Allenwood, Pa. “He was driven. While most guys would half-step a point, or leave something up to chance, he wouldn’t do that.

“Danny has cut more steel in the federal system than anyone else I’ve known of.”

Caldwell had gotten back to his job in the kitchen, where the other two were already working. But instead of going through the window, as Caldwell had done two years before, they used a fabricated key to open the door to the loading dock, a much less time-consuming procedure that correctional officers wouldn’t be on the watch for.

The hills around Marion form a sort of bowl, explains Caldwell, and during the winter the prison was frequently fogbound. They had been waiting for a milky night to launch their escape. They dubbed it “Night of the Iguana,” and when it came, they made it to the fence undetected. Then, at the fence, the wire cutters broke.

By the time a patrolling officer spotted them, Garza and Zumberge had scaled the inner fence. Caldwell, though, was too prepared. He had worn thick boots, to get him through the winter woods. But the toes were too thick to gain any traction on the chain link. While Garza and Zumberge were nearing the top of the second fence, Caldwell was still at work on the first. After one failed effort, he slowly pulled himself up, just by his arms, and became entangled in the barbed wire at the top. An officer arrived, trained his shotgun on Caldwell, and ordered him down.

Caldwell picked himself out of the wire, dropped to the ground, and started tearing up and eating the maps he had stuffed in his jacket. The three conspirators had made a pact before they set out: If any of them got out, and stayed out, he would help the others escape. But promises became irrelevant when, a few days later, federal agents apprehended Garza and Zumberge in the basement of a nearby church. Zumberge surrendered peacefully; Garza was wounded after a brief shootout.

Three failures in less than three years discouraged Caldwell, but it didn’t devastate him. No plan was flawless, the odds were always against you anyway, and he still had plenty of blades at his disposal.

The choice wasn’t quite between liberty or death, but the prospect of getting himself killed during an escape was a “small consideration” when measured against the Marion status quo. Violence inside Marion was sharply on the rise. Caldwell had personally witnessed two murders, and in 1981, a close friend, Nathan Cowger, was fatally stabbed 27 times while sitting on the toilet. Besides, rigorous planning work kept Caldwell’s mind active, especially during long stretches in the control unit.

In 1977, he started working on another way to facilitate his escape. A serial-killer friend convinced him to start writing legal briefs. Federal courts are inundated with lawsuits filed by prisoners claiming they’ve been wronged. Most are thrown out the same day. But Caldwell’s claims, like his escape plans, were the result of careful deliberation. They were solid enough, at the very least, to get him court hearings.

He wrote up complaints because he wasn’t getting Vitamin C for his glaucoma. He filed to establish nonsmoking areas in the prison. He filed for greater access to religious services. He found that the courts would take him seriously if he didn’t ask for money, but instead sought relief from existing conditions. “It was good for my head,” he says. “Keeps you sharp. Boring as hell, too.”

He achieved some degree of legal success in about half the cases he filed. But he wasn’t measuring achievement by outright victory. At best, he could feel as if he were competing with the system on equal terms, as he executed effective cross-examinations of witnesses, maybe made opposing attorneys sweat a little. About a dozen of his cases ended in published decisions, indicating that he had contributed, in some way, to the body of prison case law.

Some of his biggest successes were for other people. He wrote up a parole-oriented complaint for one inmate, Maynard Pursell, that got Pursell out of prison a year early, and then he filed a similar habeas corpus complaint that got Pursell’s son out of a Pennsylvania state prison several years before his sentence was up. A line formed outside of Caldwell’s door. “He couldn’t do them all,” Pursell says, “because his own litigation was taking up a lot of his time.”

Caldwell’s own legal push had one additional benefit. Even on losing cases, transfer to courthouses on the outside opened up new opportunities for escape. He had experienced a run of bad breaks, and now it was time to start making his own luck.

His very first civil case presented such an opportunity, though it would take five years and an unforeseeable chain of events to come about. In 1977, a federal court in East St. Louis, Ill., convicted Caldwell of his attempted escape six months before. While awaiting his appearance in court, he was housed at the St. Clair County jail in Belleville, Ill. There he was in an altercation with some correctional officers, which gave him the basis of a suit against the facility.

Five years later, Caldwell got his day in court. As a safety precaution, he was housed at the Clinton County jail, about an hour away from Belleville in Carlyle, Ill. The jail was little more than a few cells below the sheriff’s office in a small, two-story building. On the morning of June 4, 1982, Caldwell was the only inmate in the jail’s holding area.

It was a sunny spring day, and Caldwell had dressed like a civilian for his court appearance, in blue slacks, a white shirt, and light jacket. According to an official report of the incident, the Clinton County sheriff walked into the cell and handed the inmate $80 in spending money. Through some sort of “misunderstanding,” he believed Caldwell was to be released later that day. As the sheriff walked out, Caldwell realized that the cell door hadn’t closed all the way.

After a decade of escape attempts, Caldwell had set odds for himself. If he was escaping from Marion, when he could pick his moments, Caldwell figured he needed a 70 percent chance of success before the final green light. But for openings while he traveled outside the prison, Caldwell had lowered the standard to 50 percent. Here in the Clinton jail, he liked his chances.

His first thought was to walk through the door, barge into the adjoining office, and steal a gun from one of the two officers stationed there. But he let the impulse pass, pausing to consider his options. He looked through the crack of the open door into the next room, and suddenly risk assessment became moot: A second door, leading to the street, was open, too.

By that afternoon, Caldwell was sitting in a bar and grill in downtown St. Louis, eating a fish sandwich. The trip from Carlyle had gone smoothly. After crawling through the doors of the jail, he jogged to a nearby trailer park. While in prison, Caldwell had heard the names of local hospitals on the radio, and he gave $20 to a young driver to take him to one about an hour away—he told the driver a story about a sick brother. Once at the hospital, Caldwell said his brother had been transferred, and he gave him another $20 to take him to St. Louis.

Until he got to St. Louis, Caldwell’s plan had been to run as far away as possible as quickly as possible. But the next morning, he revised his getaway. He hitched a ride to suburban Florissant, Mo., and for two days he hid in the bushes of a church. Later, he learned that the delay had had its intended effect. After three days, his pursuers calculated that he was well on his way to either Las Vegas or Virginia.

Caldwell returned to downtown St. Louis and caught a bus to Chicago. Deliberately avoiding places the feds would associate him with, he then traveled on to Philadelphia, then Portland, Maine. Within about a week and a half, he made it to a rooming house in Montreal.

As Caldwell fled to Canada, a couple of factors were working in his favor. Former Marion inmates now on the outside were willing to wire him a few hundred dollars here and there, so he didn’t have to risk attracting attention by stealing. Nor did he have to worry too much about being recognized. The photo on the wanted poster showed a much fiercer-looking Caldwell than the face he normally showed the world. And the description cut 4 inches from his actual height.

For months, federal agents chased down false leads. According to documents from the investigation, agents at one point followed up a tip that Caldwell was a frequent rider of a mechanical bull at a bar in New Orleans—where Caldwell says he’s never been. Having found Astronomy magazines in his cell, they contacted Astronomy to see if he had subscribed on the outside. They printed his wanted notice in an ophthalmology journal in the hopes that Caldwell might seek professional treatment for his glaucoma. (Caldwell preferred alternative remedies, such as the Vitamin C.) One theory had it that he would attempt a helicopter prison break, and so agents reviewed the rosters of a couple of helicopter-training schools.

By the beginning of 1983, investigators had conducted 100 interviews and seized his prison correspondence with friends. But no one, on the outside at least, knew where he was.

One recent evening at his apartment, Caldwell retrieves a plastic sack from a closet and places it on his dining-room table. The sack, about the size of a kitchen trash bag, is full of small plastic baggies, one of which bears a bright orange sticker reading “Evidence. Warning!! Police Seal.” He picks up baggies at random, fishes out the pieces of jewelry inside, and then inspects them over the rims of his glasses.

Most of them are Indian pieces crafted from silver and turquoise that he bought on reservations throughout the Southwest. There are also ancient coins and antique dollar bills that he picked up at the collector shows he used to frequent. He says the jewelry trade supported him after his escape. “I think in one of my former lives I was a pirate,” he says, looking up from the stash. “I wanna get gold doubloons and go, ‘It’s mine—it’s all mine!’” He holds up one of his favorite pieces, a large silver-backed turquoise eagle that he bought for $500 in Vegas, whose wing is now chipped.

Last March, two months after his release from the halfway house, Caldwell flew out to Portland, Ore., to argue in a federal appeals court for the remainder of his assets. After federal agents caught up with him, in August 1983, the FBI seized his stash of jewelry and more than $40,000 in cash. The feds suspected that the cash and the jewelry it bought were proceeds from illegal activity.

Two friends of Caldwell’s from Marion, Terry Conner and Joe Dougherty, had recently been implicated in several bank robberies, including one in Oklahoma that netted $750,000. The two became known for their gentlemanly methods. They would arrive at the home of a bank manager the night before a heist, eat dinner with the manager’s family, and then escort the manager to the bank early the next morning, before it opened, so they could haul away the money without a fuss. Their exploits became the basis for the 2001 film Bandits. Because of their known association with Caldwell at Marion, Caldwell was suspected as the unknown third man in the heists. One bank witness claimed she heard the name Gary Caldwell. But the feds could never prove Caldwell’s involvement, nor could they prove that his seized assets were connected with anything illegal. After 17 years of litigation, Caldwell has finally won it all back, including a reimbursement for tax penalties.

Caldwell is cautious in how he talks about his 14 months as an escapee. He neither confirms nor outright denies that he was associated with the Conner and Dougherty robberies, which are now beyond the statute of limitations. “I don’t want to rub anything in their faces,” he says of the feds.

But it wasn’t a taste for crime that landed Caldwell back in prison. It was his loyalty to criminals. Caldwell’s story is this: He returned to the United States soon after escaping to Canada, and a friend lent him $50,000. He used these funds to start up his jewelry business. His first base of operations was Boulder, Colo., a place with the New Age vibe that he desired. Life was simple. Most of the time he was on the road, traveling to either gem shows or reservations, and staying in nice hotels, because “very few marshals have the per diem to stay in a place like that.” His social life revolved around his $1,500 TV and new VCR. Feeling he couldn’t trust anyone, he avoided romantic relationships—he says he didn’t want to be one of those fugitives who give it all up by talking in their sleep.

He then moved into his own three-story lodge in the mountains of Oregon, a place more remote and less populated than Boulder. And for the first time in a while, he had no real idea how he should occupy his time. “My only long-term plan was to stay out of prison,” he says. He watched videos. He bought and sold jewelry. He drove around rural highways in a ’77 Mercedes 280SL. Soon, though, he was planning another escape. Resurrecting the pact from 1979, he decided to rescue Garza and Zumberge.

He says he contacted Skip Zumberge’s brother, and through him he sent money and messages to Zumberge in prison in Lewisburg, Pa., using “the Card”—Caldwell’s nickname—as a code word. (In letters sent by proxy to Garza, he used “el Cardo.”) To help prepare the escape, Caldwell says, he moved Zumberge’s brother into his house with him.

Caldwell would later concede the ultimate futility of crime, how after a couple of successful jobs you’re bound to screw up, no matter how smart you were. He now had more to lose in busting out Garza and Zumberge than in any of his own escapes. But in his cozy house in the mountains, after more than a year of freedom, he didn’t seriously weigh the possibility of failure. The Zumberges, says Caldwell, ratted him out. Caldwell was captured while at an auto shop in Bend, Ore., where he’d taken his Mercedes to be reupholstered. (Skip Zumberge, who was released in 1989, denies telling the authorities Caldwell’s whereabouts. “He’s still saying that?” he says.)

When Caldwell returned to Marion, he got more bad news. Eros Timm, his partner in the bank robberies, had been murdered by other inmates at Lewisburg.

A few months later, in October 1983, inmates at Marion murdered two correctional officers within hours of each other, and the prison was placed on permanent lockdown. The place was now a giant control unit.

With Marion the way it was, escape was no longer an option. And by the time Caldwell reached the looser confines of Lorton, and the D.C. system, in 1994, he was too far along in his sentence for it to be worth the risk.

Not that escape wasn’t extremely attractive. Compared with Marion and Lewisburg, where Caldwell had been transferred in 1989, Lorton was a madhouse. Stabbings were frequent, the rules inconsistent, and discipline often arbitrary and vindictive. It was the kind of place, says one former correctional officer, where you could buy cigarettes at the canteen, but you would be punished for possessing matches.

Caldwell was now in the last phase of his inmate career, a time when parole hearings offered more hope of release than wire cutters. He wanted his record kept clean. So he decided to tackle the problem of getting out as an intellectual exercise rather than a physical one. Like any self-respecting inmate litigator, he was constantly at work on his habeas suit, arguing against his recent denial of parole.

But he also began using his legal tools to help impose the rule of law on an unruly place. Caldwell worked as a paralegal in the D.C. Public Defender Service’s office at Lorton, and he also worked in the prison law library, where he would frequently dispense advice. He helped other inmates file grievance paperwork when they weren’t getting proper medical treatment, or he might write up a civil complaint for them if they were being harassed by guards.

“I just didn’t want them to get away with anything when they were wrong,” says Caldwell. “I was the Ralph Nader of Medium Facility. Or maybe I should say Dershowitz.”

“In some cases he would say, ‘This case is good,’” says Mike McCarthy, a Lorton correctional officer who became friendly with Caldwell. “In other cases he would say, ‘You’re just doing this to bust the system’s chops,’ and he’d walk away. He didn’t derive any particular pleasure in destroying the Department of Corrections in the District of Columbia.”

One afternoon, in a sign of Caldwell’s shifting strategy, he warned Scott Einhorn, then a corrections officer, that the inner-perimeter gate had been left open—the kind of opportunity a younger Caldwell would have seized. In many ways, the escape artist had become a model prisoner, and he impressed his jailers by his self-discipline. “Caldwell is a very intelligent guy, and he knew how to do time,” says McCarthy. “There’s an art to doing time.”

Good behavior notwithstanding, it was clear to prison authorities that Caldwell’s legal activities were a problem. “They count on guys not being able to get competent attorneys,” says Einhorn. “They count on guys not being able to represent themselves. They couldn’t count on that anymore.”

This first became clear in 1996, when Caldwell’s cellmate in the honor unit, Frede Garcia, was having trouble with a female correctional officer named Rosamaria Chapa. Chapa was allegedly harassing Garcia because he had turned away a sexual advance. Through an inmate interpreter, Caldwell helped Garcia file an internal grievance against Chapa. As a result, all three inmates were harassed with petty disciplinary actions. Caldwell filed suit for himself and the other two inmates, claiming retaliation. A judge appointed a local attorney to represent them, and the city eventually settled the case for $50,000.

A few months after Caldwell filed the suit against Chapa and prison officials, correctional officers conducted a search of Caldwell’s cell. They said that they had received a tip that his cellmate had a knife. Instead of a knife, they produced from among Caldwell’s things $1,001 in big bills, some quarters, and a pair of cutting shears.

Einhorn was stunned. It was absurd that Caldwell would try to escape with so little time left to do, and with a parole hearing coming up. The escape kit seemed to him to be “a Hogan’s Heroes kind of thing.” Caldwell was moved to Lorton’s maximum-security facility, where he would have little contact with other inmates. Einhorn says that Caldwell may have been set up, in a move to “make him disappear.”

For Caldwell, it would get worse. While in max, he was assigned to the psychiatric unit for three months, without a psychiatric evaluation, where the inmates threw their feces at each other and at him. He was also denied treatment for his skin cancer and glaucoma. But as at Marion, he saw his circumstances as a challenge, one he was eager to confront. At the end of his prison career, Caldwell landed his biggest punches. After he filed suit on the basis of his conditions, a federal judge asked the American Civil Liberties Union National Prison Project to represent him. The group normally doesn’t take cases on behalf of individuals, but for Caldwell it made an exception. In 2001, a D.C. jury awarded him $175,000, a huge sum for a prison-conditions case. When the Department of Corrections continued to neglect his cancer treatment, he received a 2003 judgment of $55,000.

“He was serious about what he was about, and that was about making sure the prison system didn’t abuse him,” says Vince Wilkins, who used to run the Public Defender Service’s Lorton program. “And when it did abuse him, he made them pay.”

On a Friday afternoon after lunch, Caldwell leaves his downtown office and takes the Metro over to the Kennedy Center to see a matinee performance of the NSO. Caldwell now works part time for the ACLU program that represented him in his cases against Lorton and the D.C. Jail. The lawyers there became impressed by his legal know-how, and a few months after he was released, they hired him as a paralegal. He acts as a sort of filter, vetting letters and interviewing inmates to figure out which complaints are genuine. The morning before the concert, he was trying to set up an interview with an inmate in Texas who claimed he had been raped by a guard.

“I’m essentially now getting paid for what I was doing free for 25, 27 years,” he says. “But it’s not for the money. Of course, I agree with their philosophy that there needs to be independent oversight of the jails and prisons in the country, and, for the most part, it’s not done.”

Caldwell is still going forward with several cases against the D.C. system, one of the reasons he remains in Washington. His biggest case is a complaint against the D.C. Jail’s medical staff for denying him painkillers after a 2003 root-canal procedure. Jason Wallach, who represented Caldwell on his eventually successful habeas case, is also representing him on the root-canal case. Wallach says that for case research, he’ll pick up the phone and call up Caldwell. “He can find the cite faster than I can find it on Westlaw,” he says, referring to the widely used legal database.

Most of Caldwell’s calendar is filled up by work and classical performances—he has season tickets to the NSO. He never cared about the clarinet as much as he cared about the music, he says. Because the Friday performance is a matinee, Caldwell goes in the clothes he wore to work: baggy pants with lots of pockets, a long-sleeve pullover, black sneakers, and a cap advertising the Thompson Cigar Co. He says that in prison he learned to be hyperaware of his movements, and as always, he keeps his keys in his pocket carefully wrapped in a paper towel, so they won’t jingle as he walks.

Caldwell takes his seat in a middle row and places his cap on his lap, and the performance begins. The first piece on the program is a contemporary work by Donald Erb, whom Caldwell remembers from the Cleveland Institute of Music, and who is now sitting about 10 rows in front of him. Caldwell has never been too impressed with Erb, but he says that he enjoyed the performance of Beethoven’s Emperor Concerto that follows.

After intermission, Caldwell listens without any apparent feeling to Stravinsky’s thunderous Rite of Spring. At first, it seems as if after 30 years in prison, he’s just keeping his emotions to himself. But when it’s over, he leans over and offers a curt assessment. “There were a couple of ragged entrances,” he says.CP

Art accompanying story in the printed newspaper is not available in this archive: Charles Steck.