By Cheever Griffin

Lester Perry is somewhere else.

Physically he’s there on the bed that takes up much of his small room overlooking a dreary stretch of railroad in the shot-and-a-beer neighborhood of Hegewisch on the far southeast side.

But as he talks about the plane ride, he seems to leave his one-room world.

He’s a big man, six foot three maybe, with a soft frame and an even softer smile. His gray hair, dyed a sort of dull chestnut, lies neatly combed over his fleshy face, which is dominated by large, almost bulging blue-gray eyes. It is the eyes, suddenly distant and deep, that announce where he has gone.

He is back up there, 30,000 feet above the ground, holding a razor blade to a flight attendant’s neck and attempting to pull off the most brazen act in what had been a career of one bold move after another.

His look intensifies, and it seems that after nearly 30 years he still is trying to convince himself that he did the right thing.

“You gotta understand the criminal mind,” he says. “You do anything to stay out of jail.”

He holds the faraway stare a little longer and then with a blink he’s back. Back to a reality that in every sense of the word bites. Living on canned soup heated in an old microwave. Placing his milk next to a cracked window to keep it cold. Fitting all the clothes he owns into one drawer, plus a few on hangers. Walking the streets aimlessly day after day.

Lester Perry is a 60-year-old sick ex-con who, unless his fortunes change dramatically, will live out the rest of his days in a step-away-from-the-street flophouse. He never imagined he would end up this way. Yet in hindsight it all seems to fit perfectly, for Lester Perry’s life has been two stories. How he came to hold a passenger airplane hostage on a July day in 1969 is a tale of lawlessness, extravagance, and finally desperation. What happened after that is a cautionary story about a man who ended up broke, alone, and scarred by the most awful of memories.

Lester Ellsworth Perry does not look much like a gangster. Then again, who would at his age? An elderly crook is an odd sight, for there do not appear to be many around. Career criminals, it seems, are either dead by 40 or behind bars, far from society’s view. Perry, however, walks the streets in relative freedom (he is on parole) not far from where he grew up near the intersection of 106th and Torrence. He has no intention of returning to the scene of his childhood, though. As one might expect from a man who has spent almost half his days in a prison jumpsuit, Perry claims his life got off to a miserable start.

He grew up with three sisters and a brother in cramped public housing. Perry’s mother let the children do as they wished; his father, a steelworker with U.S. Steel for 47 years, made sure there was food on the table and clothes on everyone’s back. But Lester Perry Sr. was a cold, hard man, according to his kids, who provided little else.

“He wasn’t a bad person,” says Perry’s younger sister Yvonne. “He just didn’t express any feelings or show any love.”

“His only answer to anything his kids did wrong…was to whip their ass,” Perry adds. “He never knew how to love us.”

The emotional support Perry lacked at home he did not find at school. While his excess flesh now droops gently from his large bones, it’s easy to believe him when he says that at age 15 he was the class fat kid.

“I was a beast,” he says, “and because of my obesity I was unaccepted by women, unaccepted by my own friends.”

Perry dropped out of school in the sixth grade and began a life of delinquency. As his mother looked the other way–she even told school officials the Perrys had moved to Wisconsin in order to keep Lester’s truancy from disrupting the family–he took the usual steps: stealing cars, burglarizing homes, roughing up neighborhood kids. At 17 he got his first taste of a cell: a six-month sentence for breaking and entering. He walked out of prison and picked up where he’d left off. In 1959 he was sent up for burglary. He served 13 months in Joliet.

He was 23 when he got out, with no education and no skills. Worse yet, he no longer had just himself to look out for. In 1958 Perry had married Diane Hunniford, an 18-year-old neighborhood girl he’d been dating off and on, after she became pregnant.

“I didn’t really want to get married,” he says, “but I was from the old school of believing it was the morally right thing to marry her.”

With a family to support, Perry suddenly saw the road ahead of him, and it looked a lot like the one his father had taken. A lifetime of backbreaking work and nothing to show for it. He vowed not to follow in his old man’s footsteps.

“My father left nothing for me to admire,” Perry says. “He worked 50 calendar years, got his retirement and got in his rocking chair and waited for the undertaker, and I used to say you could exist for a lifetime or you could live for each moment of that lifetime. That’s what I was gonna do.”

Lester Perry wanted to live large. Right away. So he decided on a career that could accommodate his plans: stickups.

Grocery store stickups, to be precise. Shortly after getting out of the joint, Perry hooked up with a neighborhood loner named James Hannon. Perry was loud and flamboyant; Hannon was serious and reserved. Nonetheless they bonded. “We decided we were both of the same frame of mind,” Perry says. “He was always into criminal schemes.”

These days, Hannon lives in Florida. “We had a good partnership,” he remembers. “Lester was really off-the-wall. But with his craziness and my attitude, we worked well together.”

In 1961 they robbed their first grocery store. It was incredible, Perry recalls. Quickest, easiest cash he’d ever made. The two men pushed their luck and knocked over another one. And then another. It slowly dawned on Perry that he had discovered something for which he had a talent. Lester Perry had found his calling.

For the next six years, the two men engaged in a regular pattern of heading out on the road for several weeks, holding up grocery stores, and then returning to Chicago’s south side. Perry estimates that all told, he and his accomplice knocked over more than a hundred stores in more than a dozen states and took in close to $1 million.

“It was the only thing I was ever good at,” he shrugs. “I approached it professionally. When you’re sticking up places, even a lowly place like a supermarket, you still do it in a professional manner. That’s why we lasted so long.”

“For us it was just like a job,” says Hannon, sounding businesslike. “It was what we did for a living, so we were serious about it.”

Perry clears his throat and in a matter-of-fact voice, like he’s explaining how to hang wallpaper, describes how it worked. First of all, the job officially began as much as a week before a gun got drawn. For several days Perry and Hannon took turns discreetly getting to know the store, the comings and goings of its employees, the style of its manager, and, most important, the day and time that the armored truck delivered the store’s cash–usually anywhere from $10,000 to $20,000. In addition, they mapped out their getaway route and even followed the local cops around to determine their competence.

“If there appeared to be a little more efficient police station, we had to find out,” Perry says, “because everything was in the timing.”

The day of the holdup was filled with prep work. As soon before the actual job as possible, they stole two cars. One was the flashiest ride they could find, the other a beater. They parked the beater no more than eight blocks from the store and then drove up in the flashy wheels. They parked right out front.

Perry, usually dressed in a suit and hat and carrying an empty leather bag, did most of the work. With Hannon strolling the store as his backup in case anything went wrong, Perry waited until the armored truck guards left the store and then approached the manager just before he put the money in the safe. His introduction was always the same: a loaded pistol jammed into the ribs followed by a softly spoken order to quietly and calmly fill the bag with money.

“You never let anybody else know that it’s a stickup other than you and the manager,” he says. “That’s the sign of a good stickup man.”

Asked if he ever had to use his weapon, Perry shakes his head. “That was the last thing I wanted to do.” He pauses for a moment. “I don’t know if I could’ve done it.”

Perry’s victims were always most obliging. They filled his bag and then obediently accompanied him out of the store. Hannon followed behind, then ran ahead and started the getaway car. After making sure the manager got a good look at their transportation, Perry ordered him to walk to the end of the block without turning around. The two crooks sped off to the switch point, jumped into the second car, and put the town in their rearview mirror.

Looking back on it, Perry says that the decision to pick up a gun and escalate his criminal career was an easy one. It was all about money.

“It was money we could have never had a chance of making in our lifetime,” he says. “It was the kind of money that gave me independence from society, and the respectability that I so badly missed as a juvenile. I liked going back to the old neighborhood, to the taverns where it used to be, ‘Get the hell out of here, you asshole,’ to, ‘Why, it’s good to see you, Mr. Perry, can I get the door for you?'”

The overweight grade-school dropout reveled in his newfound riches and respect. He bought Cadillacs for himself and his wife. They moved into a large apartment in Calumet City and spared no expense decorating it. “It was all the best furniture,” Perry recalls. “We had wraparound couches, the best TVs they had, the best of everything. Even the drapes were the best. I remember going downtown and paying like $2,700 for bedroom drapes.”

Husband and wife made sure they looked as good as their digs. Diane bought furs and expensive dresses, while manicured Lester clothed himself in high-priced suits. “They were all tailor-made,” he crows.

The Perrys took lots of trips. They would jet off to Las Vegas, Miami, the Bahamas, Puerto Rico. “We didn’t like that place too much,” Perry says of Puerto Rico. “There wasn’t a party going on like there was in Miami. There was only a little fishing and that was it. You just laid in the sun and got drunk. That wasn’t my cup of tea. I liked the excitement, you know.”

About the only thing Perry did not do with his money was save it. “I’d be in Marshall Field’s,” he says, “and I’d see a jewelry box I liked, and the guy would say to me, ‘That’s $700, sir,’ and I’d say to him, ‘Wrap it up.’ That’s the way I liked to do it.”

“He was very gracious with his money,” says another sister, Arlene Chamnik. “He’d throw it at anyone who jumped on his bandwagon. He loved to feel powerful, and he thought that money could buy him that power.”

The somber Hannon also took to the life. He says he bought a new Cadillac every year and for a while even owned a yacht, indulging tastes that kept him in the stickup business. “It got to be that it was hard to stop,” he explains, “because you had a lifestyle to maintain.”

As the Perry family grew rich it also grew in size. The couple’s first child, the daughter conceived out of wedlock, died of a collapsed lung a week after her birth. Discussing her death still chokes Lester up. “There was something special about her,” he says. “She was so beautiful that the guy digging her grave was crying like a baby.” In the years following, Perry and his wife had three more children–two boys and a girl.

“I loved it,” Perry says. “Children are magnificent, they’re innocent, they’re pure. And just to try to bring a word of wisdom or some direction into a life is so rewarding.”

Asked what words of wisdom an armed robber might impart to his kids, Perry pauses for several seconds. “I did the best I could,” he answers. “You can’t do better in your life than your present level of awareness and understanding. I was ashamed of it in a way, but the money outweighed everything.”

Shame was never a factor for Diane. Perry says she knew all about what he did. “She enjoyed the shit out of the money. She even wished me a good stickup every time I went out.”

So enamored was she with her newly affluent lifestyle, Perry says, she tolerated a habit he picked up soon after his stickup career began: infidelity. He says his money and prestige brought him advances from numerous neighborhood women, and he rarely resisted them. Again, he felt he was making up for what he had missed in his youth. “When I was a youngster I never had women. I was fat, I was ugly. I couldn’t get done by the local whore. It had been that bad–everybody always loves you better when you have money.”

Aside from his wife, few family members seemed to know about Perry’s line of work. His sister Arlene says she figured he was involved in some sort of criminal activity, but she never knew for sure. “He used to tell my kids that he was always one step ahead of the FBI,” she says. “But we never talked about what he did. I had always assumed that it had something to do with the Mafia. But I never knew, because you never talked about it.”

Yvonne Perry also figured Lester’s new wealth was probably ill-gotten. “He was never into a nine-to-five job,” she says. “He always wanted everything so fast.”

“What can I say?” Perry says, as his face lights up with memories. “I loved the tinkling of champagne glasses and the penthouse suite.”

In 1965, after years of perfecting his illegal craft, Lester Perry did something that would haunt him. He decided to rob a bank. It was boredom more than anything else that pushed him to it. Robbing grocery stores, he says, had become rote.

“It got to be so bad,” he offers, without a hint of arrogance, “that I’d be, say, in a store in Arizona, and I’d be getting ready to do the job, and I’d be checking the prices out and how they compared to Illinois.”

Convincing Hannon to pull a bank robbery took some work, Perry says. His partner was not one to try something new. Perry was only able to talk him into it because by then they had become trusted friends.

“We got together during our time off and we did things together,” he says. “There were things I could say to him that I couldn’t say to anyone else.” Furthermore, when it came to the job he always treated Hannon as an equal. “I was the boss, but we always split the money 50-50. We were taking the same risks. He would go to prison the same as me if he got caught. They weren’t gonna say, ‘Don’t worry, you only backed him up.'”

On February 5, Perry and Hannon walked into the Security First National Bank in Downey, California, and announced a holdup. Their take was disappointing, only $5,383, according to U.S. Department of Justice records. Worse yet, the job was messy. They had underestimated the number of guards on duty and had to take a bank employee hostage temporarily in order to get out of the building safely.

Banks were not worth the risk, they decided. And so it was back to their familiar hunting grounds.

“We shoulda known better,” Perry says. “A bird knows where he feeds at and he always returns to that spot.”

Perry and Hannon dined on groceries for another three years. But in December 1967, while in Bridgeport, Connecticut, the two men again tried something different. They did a job on the fly. Once or twice before they’d hit a place without doing advance work, but it was something they tried to avoid. They considered it a move reserved for extreme cash crises–when wallets, stomachs, and the gas tank all were on empty.

The key to an unplanned stickup, Perry says, is speed. No fooling around with a manager or a safe. Get in, get what’s in the cash register, and get out. On that winter day they marked their store, waited nearby until just before closing time, and went in. With Hannon playing his usual role of innocent shopper, Perry stepped up to the checkout person, drew his gun, and quietly demanded the contents of the register.

One reason they figured they could pull an occasional quick hit was that by this time they had come to know the armored truck pickup and delivery schedules in numerous towns. Which is why Perry felt such shock when he saw two guards walk in carrying bags of change.

“We had absolutely no idea,” the old crook says, still smarting with disbelief. “Usually for that one”–the Bridgeport store–“the drop-off time was 12:30 or one o’clock. It must have been some emergency change.”

It was the beginning of the end for the two desperadoes. According to U.S. district court documents, however, they did anything but go quietly.

Finally called into action, Hannon delivered. He sneaked up on the guards with a gun and forced them to give up their weapons. He and Perry then sped off. The guards followed in their truck and notified local police of the situation. Hannon weaved through town as Perry fired at their pursuers with a sawed-off shotgun.

“I was just trying to hit their tires,” he insists, working hard to keep his gentleman-bandit image intact.

The two outlaws eventually shook the guards. They ditched their ride and frantically searched for another one. They yanked a woman from her car and took it. After driving for several miles, they dumped that car and stole yet another.

The game didn’t work. An all-points had been put out on them, complete with a detailed description of each man, and a state trooper spotted them on the Connecticut Turnpike. The chase ended a short time later in Stamford, Connecticut, when Hannon lost control of the car. Hannon, who was unhurt in the wreck, climbed out and escaped. Perry did not fare so well. He lost consciousness, and when he came to he was in a sea of uniforms. He stepped out of the car and raised his hands to the chilled sky. His long, wild, lucrative ride was over.

During the late 1960s, the world endured an unprecedented number of skyjackings. From 1950 to 1968, there had been a total of 42 attempts worldwide to hijack airplanes. In 1968 and 1969 there were 51 skyjackings in the United States alone. Most of the diverted U.S. planes touched down in one country: Cuba. It got so bad, according to news reports, that pilots began carrying maps of Havana’s Jose Marti Airport.

Skyjackers bound for the island fit no real profile. They included homesick Cubans, black nationalists, political extremists, fugitives from justice, and even a college professor who said he wanted to fight for Fidel. The only thing they shared, analysts said at the time, was desperation.

Desperate was a word that would have described Lester Perry in the summer of 1969. He was a year into a 7-to-12-year sentence for the Connecticut armed robbery. During that first year he had also been convicted of armed robberies in New York and Massachusetts. The New York conviction got him 15 to 30 years; the Massachusetts verdict bought him a 12-to-15-year stretch. The New York sentence would run concurrently with the Connecticut term, but the Massachusetts sentence was to be tacked on. At the age of 31, Perry was facing some serious time.

And when it seemed things could not get worse, the feds came knocking. The bank job, the aberration he’d practically forgotten about, had returned to kick him while he was down. The federal government wanted to prosecute him for armed robbery of a bank and for kidnapping the hostage they’d used to escape.

On the afternoon of July 30, 1969, two deputy U.S. marshals arrived at the Connecticut State Prison to escort Perry to California to face charges. The three men drove from the prison to a small town outside Philadelphia. The marshals spent the night in a motel. Perry slept at the city jail. The next morning they drove to a small airport nearby and caught a prop plane to Pittsburgh. There they boarded TWA flight 79 bound for Los Angeles.

From the time he walked out of the state prison until he reached Pittsburgh, Perry’s mind raced nonstop. He was staring down a long prison term that was about to grow longer. If he was going to do anything about it, this trip was his only chance. As he frantically plotted some kind of move, he kept returning to one idea. He was well aware of the skyjackings to Cuba, and he had heard rumors about the air pirates meeting a variety of fates–including detention and expulsion–once they landed. He decided that he cared little about such uncertainty. The way he saw it, his chances for freedom were a lot better on Cuban soil than in a California courtroom. By the time he settled into his seat on the crowded commercial flight, he had his plan all worked out.

“I wasn’t nervous at all,” he says. “I had done too much crime in my life to be nervous. And when I knew the marshals weren’t gonna put no handcuffs on me, I figured I could do it.”

With the plane over Wichita, Kansas, Perry asked to use the rest room. One of the marshals went with him and waited outside. Before going in, Perry notified his escort that he had with him his makeshift toiletry kit–a worn envelope containing several bathroom items, including a razor. The marshal apparently thought nothing of it.

Inside the rest room, Perry removed the double-edged razor blade and positioned it between his fingers. He then opened the door and dashed toward the cockpit, away from the marshal. He grabbed the first flight attendant he saw and placed the blade to her throat. He ordered the marshal back to his seat and then marched the flight attendant into the cockpit. Perry informed the flight crew of their new destination. He told them he would kill the stewardess if they resisted him. He also lied and said he had hidden a bomb on board. He locked the cockpit door behind him, tightened his hold on his hostage, and settled in for the ride. Three hours later the plane touched down in Havana.

As he relives the episode yet again, Perry’s thousand-yard stare returns. As does his simple defense. “I didn’t have no choice,” he pleads. “It was either go to Cuba and the possibility of some type of freedom, or spend the rest of my life in jail in America.”

But his voice seems weak and without conviction, and one gets the sense he knows that on that summer day so long ago he made the biggest mistake of his life.

Perry was taken from the plane by Cuban authorities and interrogated for several days at a government facility he came to know as G-2. He told them over and over that he was a fugitive trying to avoid an extended jail term in America. The Cuban government branded him an agent of the CIA and threw him into prison without a hearing or trial.

He spent the next 11 years there.

That is where the official story of Lester Perry’s lost decade ends. Declassified State Department documents confirm that he was a prisoner in Cuba from shortly after he arrived in 1969 until he was expelled from the country in late 1980. The rest of the tale is Perry’s, and the prospect of having to rely solely on the word of an ex-con is slightly troubling. But as he describes his ordeal, the occasional swelling of his eyes and cracking of his voice conveys, beyond any of his words, the dreadfulness of what happened to him down there.

“What can I say?” he says, forcing a small smile. “I went from the frying pan to the fire.”

The first five years were the worst. He spent all of them at G-2, in a small, windowless cell composed of three concrete walls and a large steel door, with nothing but a hole in the floor for relieving himself and a board on which rested a thin mattress and half a blanket. The guards fed him by shoving meals through a slit in the door.

“I can tell you the whole menu in one breath,” Perry says. “In the morning you got a half a cup of sugar water and once or twice a week a piece of bread, and when I say rotten I mean green all the way through. But you were glad to get it. For lunch it was boiled noodles, and for dinner it was a little shark meat, the greasy black part, and some rice.”

Perry says he believes he was interrogated only two more times during his stay at G-2. He remembers them as the only times he got chocolate cake. On each occasion a guard slid the dessert under his door, and after eating it Perry remembers falling nearly unconscious and being taken from his cell. The next thing he recalls is waking up back in his hole with a needle mark in his arm.

“Who knows what it was, truth serum or something like that,” he says. “But there was nothing to tell them, because I wasn’t no G-man.”

Asked why he ate the cake the second time, knowing what might happen to him, he looks as if he has just encountered the silliest question in the world.

“You ate anything they gave you,” he replies.

Worse than the meager rations, he says, was the isolation. He went months without seeing anyone, and he can count on his right hand the number of times he was let out of his cell. For five years he just sat there.

“One day you lose,” he says, “then you lose a week, then a month, then you don’t know what year it is. At some point you wonder whether you’re still alive.”

The loneliness and monotony got so bad, he says, that he took to talking to himself, as well as to the cockroaches that infested his cell. “You never killed them, because they were all you had.” His voice begins to shake and he stops to compose himself. “It sounds like insanity, but it was insanity to keep your sanity. You talked to roaches because the door never opened. It just never opened.”

Finally let out of G-2, Perry says he spent the next five years in four different prisons–a year or so at each. He was moved around with a dozen other American prisoners, including several skyjackers, and though he was no longer in isolation, life did not get much better.

One of the prisons they stuck him in was what he calls a Cuban “concentration camp,” where he and his compatriots did time with the island’s most hardened criminals. Perry says he endured numerous beatings from guards and inmates and witnessed knife fights daily. He even saw a man die.

“His name was Lonnie,” Perry says. “He hadn’t had a shower for a year and a half, and one night he starts screaming for a shower and he won’t stop. So the guards drag him out and beat him to death and leave him there for everyone to see.”

Perry began to think about giving up. “I was at the end of my ability to go any further,” he says. “I figured it was better to be dead than to be alive.”

Hopelessness drove him to thoughts of suicide. It sounds perverse, he says, but he actually was distraught that the Cuban government did not single him out for torture or interrogation. There was nothing special about him. The Cubans, he believed, were content to simply forget about him and let him die in prison.

The lack of attention paid to him back home only added to his despair. An old State Department memo indicates that in the weeks following the skyjacking, the U.S. government did attempt to get Perry back. The United States did not and does not have formal relations with Cuba. So through the Swiss embassy in Havana it asked the Cuban government to return Perry. Cuba refused, and after that Uncle Sam apparently made little attempt to retrieve one of his less-than-model citizens.

A State Department spokeswoman has declined to comment, citing a lack of adequate records on the decades-old affair.

Perry heard nothing from his family. Arlene Chamnik insists that she and her siblings tried to communicate with him, but to no avail. One day “the government tells us that it lost track of him,” she says. “After that, we thought he was dead.”

Close. Perry says he was ready to die. He followed the lead of several other inmates and began a hunger strike to protest prison conditions. The Cuban authorities responded by taking him to a hospital and placing him on a bed in a room with other hunger strikers–and leaving him.

“They were saying to us, ‘You go ahead and die. We don’t care,'” Perry says, his voice trembling again, this time with anger.

He called their bluff and refused food for more than three weeks. One day he turned and saw that a hunger striker who’d had a two-week start on him lay dead in his bed. The Cubans had meant what they said. With death suddenly less abstract, Perry folded his cards and ended his strike. He did not want to die after all.

His fortunes took a turn for the better after that. He was transferred to what he describes as a jail for “political prisoners.” The inmates there helped him to regain his physical and mental strength. “They were the most beautiful people I ever met,” Perry says. “Intelligent, strong, and they really pumped me up.”

In late 1980 officials took Perry from his prison and brought him to a small room in a nearby government building. They sat him down and told him what he’d thought he would never hear: he was free to leave Cuba. They offered no explanation for letting him go. Earlier that year Castro had let tens of thousands of Cubans–mostly people he considered undesirables–leave the country. Perry says he figured it just took them a little longer to get around to him.

Before releasing him, however, the Cubans insisted he sign a paper confessing to a number of charges, including acting as an agent of the United States and committing slander against the Cuban state.

“They said, ‘You have a choice, Perry. You either sign this confession, or we can’t let you go, because we gotta justify having you. So sign on the line or die here in Cuba.'”

Perry had a condition of his own. He figured a direct flight to the United States would merely change his prison scenery. So he insisted that they release him to another country.

To his astonishment, the Cuban authorities agreed. Perry signed the confession, and a few days later he was on a plane bound for the Caribbean island of Barbados. He scraped together some money to add to the $130 the Cubans had given him and bought a plane ticket to Toronto. Shortly after arriving in Canada, he crossed the border into Detroit. After figuring he would never see it again, Lester Perry was back on American soil.

Perry returned to the United States a changed man–at least physically. He was much thinner, having lost more than a hundred pounds in Cuban prisons. He quickly realized that his country also had a new look.

“Everything was so new and strange,” he says, “the cars all speeding by, the people dressed in different clothes. I felt like I was drunk. It was a real culture shock.”

Bewildered by a society he hardly recognized, he fell back on the only thing he knew. He boarded a bus going anywhere–Columbus, Ohio, as it turned out. When he arrived he found the nearest toy store and stole a plastic handgun. He then used it to hold up a local supermarket.

“I was lost,” he says, explaining why he so quickly reverted to his old ways. “I was truly lost.”

He fled Columbus with about $4,000 and went to Butler, Pennsylvania. There he rented an apartment and applied for a gun permit, using a phony name. Some weeks later, he traveled back to the buckeye state and knocked over a supermarket in Youngstown, again using a toy gun.

He took in a few thousand from that job and this time he headed west, back home to Chicago. Like everything else, the city’s southeast side had changed while he was away. Perry learned shortly after arriving back in town that his wife had divorced him in 1976. He recalls reacting with little surprise. “She was an eloquent woman and I loved her,” he says. “But there really wasn’t no happiness in the marriage. It was just about the money.”

What did jolt him was the news of whom she’d married: James Hannon. Authorities had caught up to Hannon in 1970 and arrested him for his role in the California bank robbery. He spent a couple of years in prison for that, and a couple more for a Rhode Island stickup, committed after he and Perry split up and he hooked up with a group pulling armored car robberies. Paroled in ’75, Hannon married Diane and gave up the life. “Enough was enough,” he says. He does construction work now, and some plumbing on the side.

“I didn’t think it was right, his partner and all,” says Perry’s sister Arlene. “But I always knew they had something going. They had an eye for each other.”

“I can’t imagine what my wife would see in him,” Perry says, his eyes, at least now, void of any hurt. “But she evidently always liked him.”

“It just happened,” says Hannon. “We grew up together and we were always fond of each other.”

Most of the other people Perry had run with were gone by 1981. With so few familiar faces, he saw little reason to stick around the old stomping grounds. For one thing, it was the middle of January, and his years in the tropics had weakened his tolerance to Chicago winters. In addition, with the feds surely trying to track him down, settling back home would not be the wisest of moves.

He decided on Florida. Prosecutors would argue that he intended to hook up with some drug smugglers he’d met while imprisoned in Cuba, but Perry insists that he simply wanted to start his life over.

“I figured I’d get down there and maybe look for some work,” he says. “What I needed so badly was rest and recuperation. I needed to find some sanity in my life.”

His old spending habits got in the way, however. He had blown nearly all his money, and he had barely enough to travel with, much less buy a car. His attempts to obtain a gun had failed, and without a real piece of hardware he was reluctant to try another stickup. So he decided to brush off his hot-wiring skills.

To be safe, he went out of state for the vehicle. In February of 1981 he traveled to South Bend, Indiana. He entered a random parking lot and worked his way into a car. If he still had any lingering doubts about how much things had changed while he was gone, the first maddening moments in the front seat erased them. He couldn’t get the car to groan.

“When I left, stealing a car was simple–you could start one as fast as if you had the key.” He waves a disapproving hand at the air. “Now it was a real trick. It was in the dashboard or something like that.”

Perry next made what he admits was a major blunder. In a situation that called for doing the job quick or getting out, he hunkered down and lost himself in trying to conquer the new and stubborn system. He didn’t even see the security guard until the man was shouting at him from outside the car, his gun drawn.

After less than three months on the outside, he was on his way back to jail.

At this point, the legal proceedings got complicated. After sorting through old sentences and new convictions and dropping various charges, the court handed Perry his punishment: 25 years for air piracy and 25 years for armed bank robbery. The sentences were to run concurrent with each other and with the remaining Connecticut and Massachusetts sentences.

On June 21, 1981, Perry returned to the Connecticut State Prison to finish what he had started more than 12 years before. In 1988, with the Connecticut sentence up, officials prepared to transport him to Massachusetts. But a slight problem arose. Massachusetts could find no records on his nearly 20-year-old conviction. Without such documents, the state could not hold him, and so instead of traveling up the eastern seaboard, Perry was transported to the federal prison in Lewisburg, Pennsylvania. He remained there until the summer of 1994, when he was granted parole.

By then, however, authorities in Massachusetts had their papers in order. And they wanted to see Perry do time in their state. As a result, Perry sat in a Massachusetts prison cell for nearly three more years as lawyers with Massachusetts Correctional Legal Services fought for his release, arguing that Massachusetts had had its chance to take him earlier and blown it. A court eventually agreed, and in early 1997 Perry’s cell door swung open. After spending more than the past quarter century behind bars, Lester Perry, then 59, was a free man out on parole.

He made his way back to Chicago and checked in with his probation officer. He then bounced around several halfway houses before settling in this dreary three-story red-brick building, home to numerous other down-and-outers.

“From the palace to the barnyard,” he smiles as he surveys his barren living space. The smile then vanishes. “It’s been a long fall, my friend.”

Perry is having what he calls one of his bad days–a day when one of any number of ailments from which he suffers rises up and takes hold of him. Today it’s his back pain, which has him laid out stiff as a board on his bed. He attributes this particular debilitation to the beatings he took in Cuba. He rolls gingerly on his side and points toward his lower back. “It was always with rifle butts,” he says stoically.

According to prison records, Perry is not a well man. In addition to a bad back, he has a brain tumor that causes severe headaches and seizures. He also has arthritis and is legally blind in his left eye. He takes 13 different pills each day, and once a week he goes for an injection of anti-inflammatory steroids.

In one way, his ill health is a blessing. It provides him with his only source of income. Each month he receives $494 in social security disability. He pays $200 in rent and spends another $100 on various medications. What’s left has to last him until the next check. He claims to have tried numerous times to find a job since returning to Chicago. But he adds that elderly, frail ex-cons are not in high demand.

“Door after door got slammed on me,” he says. “They says, ‘You gotta be kidding me. We’re not hiring no gangsters today.'”

And so Lester Perry spends his days doing very little. He may shoot the breeze with his neighbors, walk the neighborhood, or just lie in bed and listen to his small plastic radio.

His sisters come around every once in a while to check up on him, as do several nieces and nephews. But most days he is alone. His ex-wife is still happily married to his ex-partner in Florida, which is where his two remaining children also live (his son Lester Jr. died of a drug overdose years ago). He hasn’t spoken with any of them in years.

As James Hannon sees it, Perry has reason to be grateful to him. “I helped raise the kids,” he points out. As for marrying Diane, “Who better than me? I always assumed Lester thought highly of me. If he cares anything about her, he should know that she’s happy, and he should be happy with that.”

Hannon, for his part, feels a debt to the old comrade-in-arms who took the fall alone back in Connecticut. “He never mentioned my name,” Hannon says. “He could have cut himself a break and he never did. I appreciate that.”

Hannon says he doubts his wife has anything to add, and declines to call her to the phone.

Perry says what he ultimately wants to do is leave town and get away from what he calls the “ugly circle” of people around him. “They all follow the coke and the crack,” he says. “One thing I haven’t done is let that stuff get control of me.”

Where he would go, however, is unclear. One day he talks about moving to Spain. The next day he expounds on starting a farm in Oklahoma. Lately he has gone on at length about opening a trinket shop in Las Vegas.

“You ever been to Vegas?” he asks, and doesn’t wait for an answer. “Most beautiful food at a fraction of what it would cost you around here. You sit down to breakfast out there, and it’s food as far as the eye can see.”

To accommodate his travel plans, Perry has been trying to get his parole terminated. It’s not up until 2006. An official with the federal defender program says the office has been working off and on with Perry to locate a special judicial order Perry claims grants him credit for his prison time in Cuba. Such an order, the official says, would provide Perry with a strong argument to have his parole reconsidered. Without it, shedding his parole restrictions will be next to impossible.

United States statutes regarding sentence computation state in part that “jail time credit will not be given for any portion of time spent serving another sentence, either federal or non-federal.” Because Perry’s jail time in Cuba was unrelated to his sentences in the United States, it normally couldn’t be used to shorten them. Perry’s special order, if it does exist, would represent a rare case of judicial magnanimity.

Yet even if his parole were to end tomorrow, it is hard to imagine Lester Perry going anywhere.

To be sure, he makes a gallant effort– keeping himself clean-shaven and well groomed, disarming visitors with a quick joke and a light demeanor. But his spirit, like his body, is broken.

“I see a man who’s laughing on the outside but crying hard on the inside,” says his sister Arlene. “I don’t know how anybody could’ve survived all he’s been through. He used to be so alive. Now he’s just a broken-down old man.”

In a moment of self-reflection, the old stickup man admits as much. “I just don’t have a grip on anything anymore,” he says softly.

As he lies there on his aching back, staring at the ceiling, he seems sure of only two things. The first is that the way his life has turned out is no one’s fault but his own. “There’s nothing to feel sorry about,” he says. “I chose the path I took. All of this is the result of my own ignorance and stupidity.”

The second is that he’s had his last look at the inside of a jail cell. “I won’t be going back,” he says. “I sit here with two cents, but I’m living with that. At one time that would be unheard of–I’d go out and steal the tires off a car.” He pauses and shrugs peacefully. “I don’t chase the dollar anymore.” o

Art accompanying story in printed newspaper (not available in this archive): photograph by Lloyd DeGrane.