It’s 10 p.m. on august 22, 2010. The escape artist throws open his prison cell window and tosses three six-foot sections of copper piping out into the yard. Even though he’s done this sort of thing a half-dozen times before, he’s still nervous. He knows he has 50 seconds to breach three fences, one of them pulsing with lethal electricity, and he’s thinking, Fuck. This is it. Clock’s ticking.

His feet hit the dirt about 10 feet below the cell window. His hands corral the pipes, and he quickly assembles them like Lincoln Logs into an 18-foot ladder. Then he sprints across nearly 100 yards of empty space, with no cover. He runs like a maniac, avoiding the floodlights with his clanging metal ladder in tow.

Forty seconds.

First fence. The ladder reaches clear to the razor wire spooling the top, and he scrambles up. He reaches the top and is about to go over when—Oh shit, oh shit, oh shit…. His foot’s stuck in a coil of razors. The ladder slips. He looks back toward the prison and sees his fellow inmates staring from their cells. I’m busted. It’s over. I’m done….

Then, for a moment, everything goes still. The view of the prison from the top of the fence is suddenly like a hallucination that bursts open all five of his senses. The wind, blowing some 40 miles per hour across the scrubby eastern Colorado plains, whips in his ears. He can smell the dirt being kicked up in the yard.

He snaps out of it: Go. Thirty seconds.

His foot slips free, and he sprints toward the second barrier—the “kill fence,” the one supercharged with a high voltage current. But he’s prepared; thanks to his prison maintenance job, he knows electricity can’t kill you if you’re insulated. He pulls out cardboard boxes and a shower curtain tucked into his pant legs and lines them up on the ground to create a portable tunnel. He slides underneath the fence.

Twenty seconds.

The last part is easy. The final fence is designed more for keeping regular people out than inmates in. Up, over, and he’s gone, sprinting through the surrounding prairie and farmland. No looking back. Douglas Alward is finally a free man.

Except, of course, he’s not. Alward, now 52 years old, tall and ropy with a shaved head, graying goatee, and lively blue eyes set behind metal-rimmed glasses, is a convict who’s escaped seven times yet never really gotten away. He shifts in his seat behind a glass partition in the visiting room at Sterling Correctional Facility, the same maximum-security prison he once gamed so easily it was like the guards weren’t even trying. (As Kellie Wasko, deputy executive director of the Colorado Department of Corrections, recalls, “He made the friggin’ ladder and laid in his bunk every night looking at the ceiling, thinking: Idiots. My ladder is right there above my head.”) But he’s been in the prison’s solitary confinement wings ever since a bevy of gun-wielding lawmen surrounded him three days after he last fled. Four years later, confined within stark cement walls and under glaring fluorescent lights, he’s still trying to figure out what exactly went wrong.

The problem with escaping from prison is that outwitting guards, assembling and hiding the necessary contraband, breaching razor-wire fences, and sprinting into the night is all just step one. The vast majority of prison breakouts end in capture, possibly because would-be freedom-seekers spend all their energy on how to actually escape. The “staying free” part is mostly left to chance. If you haven’t nailed down the logistics for a life on the lam—a vehicle on the outside, cash, a new ID, a crew to smuggle you across a border—where do you end up?

You end up back inside.

“It’s not like I didn’t have a plan,” Alward insists. In fact, he had an ingenious one, two years in the making. It began with a job. One unintended perk of a prison maintenance job is that it teaches you what implements you need to escape and how to get them. It gives you access to things most inmates don’t have: tools. Locks. Tamper alert material to cover up seals you’ve broken. It creates certain educational opportunities, such as learning about the intricacies and alchemy of electricity—knowledge that can later be applied to beating a kill fence.

Working in maintenance also means you’re asked to do things like change out cooling systems, which is how you’re able to smuggle away and hide 36 feet of copper piping. The job has you rivet shut the windows in every cell. (Except yours, of course. That one, you rig.) Over time you collect a smattering of objects that can be turned into instruments of evasion. You know where to hide them: inside wall panels across the hall, above the ceiling panels in your cell, the locks of which you pick and then repair. No one will ever suspect a thing.

On the night of the escape, you tie it all underneath your bunk, and you wait for the routine to unfold just like you’ve studied it for months: the guards, their habits, their shift changes. By now you know the precise movements of the perimeter vehicles, everything from how often they circle the prison to the exact times when, thanks to bureaucratic mandates, they’re locked between two gates for inspections, leaving the outside of the prison relatively unguarded, if only for a moment. Once you’ve mastered the procedures, you figure out how much time it takes to get from within your cell to the great, unshackled beyond. After all those months of scrutiny, you calculate the magic number: 50 seconds. And it all works beautifully—until it doesn’t.

Alward’s life has been a pattern of catch and release…and catch again. He once stole a bus from the Buena Vista Correctional Complex garage, threw it into gear, and busted down the gates. He then ditched the bus and jumped into the nearby Arkansas River. The cops found him floating downstream in an inner tube within an hour. Another time he stripped naked at 2 a.m. in his Florida jail cell, lathered his body in shampoo, squeezed through a food tray slot between the metal bars, and started walking nonchalantly away. The searchers found him wandering the streets in a shampoo-soaked jumpsuit before he could get across the nearby town. Then there was the time he was sent to a Denver hospital for a severe foot infection—he’d aggravated his own wound to ensure he’d require medical treatment, hoping a civilian hospital would give him a chance to flee—and figured out how to use the mechanical bed to break his chains. He eluded capture for a few weeks, probably his best chance to truly disappear for good—until he got cocky and decided to send a postcard from New Orleans to his most recent sentencing official, “that punk-ass Judge Eakes.” Then he continued on to Florida, got careless, and called his father—and his father called the authorities.

After seven breakouts over 40 years, Alward has extended what was initially a 10-year stint for attempted murder when he was 17 to what will almost certainly be a lifetime behind bars. It’s gotten to the point at which the only way he’ll ever see the outside world again is to plan his next escape. The way he sees it, what’s he got to lose?

Douglas Alward felt imprisoned long before he ever saw the inside of a jail cell. The beatings started sometime before he was nine years old. He doesn’t remember when they actually began, only that they never made sense. He once stole a bicycle inner tube from a local store, and his father, perhaps sensing a teaching moment, left him welted and bruised. (Alward also recalls that a few weeks later, his old man swiped a package of brake lights because they were “too expensive.”) Sometimes his father pounded him for no reason at all. Alward started acting out in school and spent most of third grade at a desk exiled to the hallway. Around that time, his mother killed herself. His sister would eventually do the same.

Alward found an alternative escape at 12 years old by smoking marijuana and fleeing from home on his bicycle. He started stealing cash from people’s houses, usually making sure to vandalize something on his way out. At 13 he tried to burn down his junior high school with a fire bomb and was sent to what he calls the “nuthouse,” a clinic for the mentally ill. Sometime after he was released from there, he stole a car and wound up lost in some desolate Missouri nowhere during a blizzard. Doctors had to amputate all the toes and a chunk of his left foot because of the frostbite.

Then, at 15, Alward rolled his father’s car and got sent to another mental health institution. It was June, and his stepmother sent him his winter jacket, which meant they intended to keep him there for a while. Not gonna happen, he thought. He fled to Oregon with his girlfriend, lived in an abandoned amusement park called Pixieland with a bunch of hippies, and started doing B&Es along Highway 101—that is, until the time the cops were waiting.

Then it got worse. One morning when Alward was 17, he broke into someone’s house while carrying a knife. The owners awoke to find the teen pillaging their belongings and shot him in the chest, but not before he stabbed them both. Blood was everywhere. “A big melee,” Alward says now. “A shock that no one ended up dead.” The crime landed him a 10-year minimum sentence, an eternity to the 17-year-old Alward. If he had just ridden it out, he would have been free 25 years ago.

Instead, at 52, he’s slowly turning into the old man behind bars he always feared he’d become, still caged the same way he’s always been and always felt, still trying to find a way outside, a claustrophobe in a room that shrinks whenever he moves.

The lights in the visiting room illuminate Alward’s blue eyes, a shifting mixture of patience and rage, kindness and humor, mischief and deceit. To illustrate the size of the box in which he now lives, in which he’ll probably always live, he extends his arms; he can touch both sides of the room without extending to his full wingspan.

That’s why he’ll likely keep doing what he’s always done. He’s getting older, maybe soon he’ll even be “too old for this shit”—but not yet. He’s thinking about Sterling’s vulnerabilities: I won’t be in solitary forever, you know. “The razor wire on the perimeter fences doesn’t hurt that bad,” Alward says, as other thoughts—about how to beat the kill fence and what he’d do differently the next time—trickle almost visibly through his mind. “I’m a prisoner. It’s my job to try and get out of here,” he finally says with a laugh. “It’s their job to try and keep me in. I don’t know why everybody’s gotta be so serious about it.”