In exchange for another eight years in prison—and the chance to be a free man in Canada long before that—Omar Khadr consented to a long list of strict conditions. He cannot sue the U.S. government for damages, regardless of how many torture sessions he may (or may not) have endured inside the barbed-wire walls of Guantánamo Bay. He will never step foot on American soil for as long as he lives. And he is not allowed to profit one penny from public speaking tours or movie deals or anything else that would involve selling his saga to the highest bidder. Any such proceeds, the agreement says, will go straight “to the Government of Canada.”

Khadr has read a lot of books during his stint behind bars (from steamy Danielle Steele novels to Nelson Mandela’s Long Walk to Freedom), and his pen pals include an English professor at an Edmonton university. But when he signed his name to that seven-page plea deal on Oct. 13, he received a first-hand lesson in the meaning of irony: the same government that spent many years and millions of dollars fighting to keep him out of Canada now owns the exclusive rights to his life story.

Perhaps it’s only fitting. At 24, Omar Khadr has never truly been in control of his own life. Brainwashed by a fundamentalist father, raised in the shadow of Osama bin Laden, and sent into battle as a Kalashnikov-waving teenager, he is—in the famous words of one Foreign Affairs bureaucrat—“a thoroughly screwed up young man.” Since his capture in 2002, Khadr has been manipulated by fellow inmates, abused by interrogators, ignored by his home country, abandoned by a long list of court-appointed lawyers, and exploited in ways that even he doesn’t realize yet. Human rights activists, anti-war protesters, opposition politicians and terrorist sympathizers all claim him as their own.

But today—after spending more than one-third of his life locked inside the world’s most notorious cage—Khadr finally has the chance to be his own man. By pleading guilty to five war crimes, including the murder of a U.S. special forces soldier, the Toronto native will serve just one more year in Cuba, followed by a transfer to a Canadian penitentiary. Twenty months after that, in June 2013, he will be eligible to apply for early release.

When that day comes, the National Parole Board will have to answer the one question that remains a mystery: who is the real Omar Khadr? The hardened terrorist who basked in the glory of killing a Delta Force medic? Or the innocent child soldier who desperately deserves a second chance?

The competing narratives could not be more different. The only common thread is that neither is completely believable. If anything, the truth lies somewhere in between.

According to the U.S. government, Khadr remains a real and dangerous threat—a “rock star at Gitmo” who has spent the formative years of his life “marinating in a community of hardened and belligerent radical Islamists.” In his own statement of facts, the cornerstone of his guilty plea, Khadr admits that he was a loyal member of al-Qaeda, was obsessed with killing Americans “anywhere they can be found,” and that the “proudest moment of his life” was when he built and planted improvised explosive devices aimed at coalition troops in Afghanistan.

When prison guards gave him a hard time, Khadr would recall how his grenade killed their comrade, Sgt. Christopher Speer, “and it would make him feel good.”

But according to his supporters—and his own spoken words in court—Khadr is a “gentle giant” who has denounced violence, apologized to Speer’s widow, immersed himself in books, and dreams of one day becoming a doctor. “You’re not going to gain anything with hate,” he told the jury at his recent sentencing hearing. “I came to a conclusion that love and forgiveness are more constructive and will bring people together and will give them understanding and will solve a lot of problems.”

Khadr has pored through Pride and Prejudice, Barack Obama’s memoir, and each instalment of the Twilight series. He has crayons in his cell, and draws pictures of lakes and flowers and other scenes he longs to see with the one eye that wasn’t blinded by shrapnel. “No matter how abandoned he’s been, he doesn’t have any anger,” says Dennis Edney, Khadr’s long-time lawyer. “He is a kid who is going to go back to Canada and start his life, and Canadians will see that this young man is harmless, and that he is a victim.”

When asked how the same boy (now man) can be a proud murderer and a harmless victim all at the same time, Edney is blunt. The agreed statement of facts “is fiction,” he says, and Khadr only signed it because he knew that admitting guilt was his only hope of ever leaving Guantánamo Bay. “Anyone who believes this was a full voluntary confession is crazy,” Edney says. “If they had asked him to plead to the shooting of John F. Kennedy, we would have agreed to that, too.”

The story of Omar Khadr (a narrative that now belongs to the feds) began in a Toronto hospital on Sept. 19, 1986. But it would be another 10 years before the country was first introduced to the curly-haired boy destined to become an “enemy combatant.”

At the time, Omar’s father, Ahmed Said Khadr, was in the custody of Pakistani authorities, accused of financing the November 1995 bombing of the Egyptian embassy in Islamabad that killed 16 people. A Canadian citizen, the Khadr patriarch proclaimed his innocence, embarked on a hunger strike and ended up in the headlines—just as Jean Chrétien, then the prime minister, was flying to the region for a trade mission. Under pressure from the press, Chrétien agreed to broach the case with Pakistani officials, and took time out of his busy schedule to meet Khadr’s wife and young children. Including Omar.

A few months later, Ahmed Khadr was a free man, kissing the ground after his plane touched down in Canada.

It turned out to be a short visit. Before long, he and his family were back shuttling between Pakistan and Afghanistan, mingling with al-Qaeda elites and using his “charity” work as a front to finance bin Laden’s training camps. In 2001, Ahmed Khadr’s name was added to a United Nations’ terrorism blacklist, and when the World Trade Center was toppled later that year, the U.S. branded him a “primary suspect” and froze his assets.

A week after 9/11, Omar turned 15. It would be his last birthday with his family.

In June 2002, as coalition forces hunted for bin Laden and his associates, Ahmed Khadr sent his teenaged son to serve as a translator for members of the Libyan Islamic Fighting Group, a terrorist organization linked to al-Qaeda. (Omar is fluent in English, Arabic, Pashto and Dari, and can also speak some French.) But he did much more than talk. Khadr was trained to fire rocket-propelled grenades, assault rifles and pistols, and was soon assigned to a cell that built and planted powerful IEDs. A home video released by prosecutors shows a grinning Omar Khadr constructing his homemade bombs and holding the Quran.

His duties also included undercover reconnaissance. “On at least one occasion,” says the agreed statement of facts, he “clandestinely spied upon U.S. troop movements near the airport in Khowst, Afghanistan. Omar Khadr did not wear a uniform and attempted to blend in with the civilian population in order to gain as much actionable intelligence as possible.”

On July 27, 2002, less than two months after his father dispatched him to the front lines, Khadr found himself holed up in a mud compound in the village of Ayub Kheil, surrounded by dozens of U.S. troops. Women and children were allowed to leave, and everyone else inside was offered multiple chances to surrender. Khadr stayed put.

Four hours later, after U.S. warplanes annihilated the compound, a group of elite Delta Force commandos made their way inside. “The unit began taking direct fire from an AK-47,” reads the statement of fact. “One soldier saw the individual firing the AK-47, engaged and killed him.” Khadr, hiding behind a wall, pulled the pin from a Russian-made grenade and tossed it in the soldiers’ direction (“like in the movies,” he later told an interrogator).

An American returned fire, hitting the 15-year-old with two bullets to the back.

“Omar Khadr and the others made a pact that they would rather die fighting than be captured by U.S. forces,” the agreed statement says. “He believed he would likely die in the firefight and wanted to kill as many Americans as possible before being killed.”

Khadr, of course, did not die. But Sgt. Speer did, leaving behind a wife, a three-year-old daughter and a newborn son. He was not killed instantly, though. Khadr’s grenade ripped open his skull and peppered his brain with shrapnel, but Speer hung on for 10 more agonizing days before finally succumbing to his injuries.

As Speer’s body was being flown back to North Carolina, Khadr was recovering from multiple surgeries at a U.S. military hospital in Bagram, Afghanistan. For one procedure, the only ophthalmologist in theatre was rushed in to perform a vision-saving operation on his right eye. It would be another six weeks before the Canadian Embassy in Washington learned that one of its citizens was in U.S. custody, and even then, the details were sketchy (except for a Washington Post article that claimed Khadr was “singing like a bird” to interrogators).

In the eight years since, nothing we have learned about Omar Khadr proves, with any certainty, what he is thinking or who he has become. It’s hard to imagine that even he fully understands what’s swirling in his head, but even that would be an assumption. All we know for sure is that Khadr has spent more than 3,000 days and nights in a place that would damage even the strongest of minds.

And a place where torture was standard operating procedure.

Khadr confessed, on numerous occasions, that he threw the grenade that fatally wounded Sgt. Speer. At times, he described that day with obvious pride, well aware that his battlefield kill had won him the respect of fellow detainees. One FBI agent described his demeanour as “cold and callous.”

But Khadr would later claim that he was horrifically abused—and even threatened with gang rape—during his interrogations. In Bagram, where he spent three months before his transfer to Guantánamo, the 15-year-old was questioned more than 40 times, sometimes in a room with barking dogs, sometimes while hung by the wrists. During one session, he says someone placed a hood over his head and soaked him with water until he began to suffocate.

The tactics continued in Cuba. Khadr claims he was left in isolation for up to a month, spat at by an interrogator, and shackled to the ground for hours on end. Once, when he was tied up for so long that he urinated on the floor, guards used him as a “human mop” to clean up the mess.

Agents from CSIS, Canada’s spy agency, visited him in February 2003, and as video cameras rolled, Khadr told the agents he had been “tortured” into confessing and that he didn’t throw the grenade. When the spies left, Khadr sobbed uncontrollably, crying out for his mother. He was 16. (A new documentary, You Don’t Like the Truth, includes long snippets of the videotaped interrogation, as well as a rare photo of Khadr as he looks today.)

Did those first few months in custody reinforce Khadr’s commitment to jihad? Did he wish that he killed 10 Americans, and not just one? Or was he angry at his father, a man who could have raised his kids in Canada but chose holy war instead? Only Khadr knows the answers to those questions—and his actions (or at least those that have been documented) don’t offer any obvious clues.

Consider this scene in March 2004, when a Foreign Affairs official flew to Guantánamo to visit him. At one point, Khadr was handed a photograph of his family and left alone in the interrogation room. He urinated on the picture—twice. And then he laid his head close to the photo in what one observer described as “an affectionate manner.”

“[Omar] does really not understand the gravity of his situation,” wrote R. Scott Heatherington, a senior official in the Foreign Affairs intelligence division. “Before he is returned to Canada (if this were to be a possibility) some thought should be given to ‘managing this process’ and the social services agencies should play a major role.”

A year after that consular visit, Khadr was charged with murder and ordered to stand trial in front of a military commission. He continued to insist that he was not to blame for Sgt. Speer’s death, and that his confession was coerced. By then, home was a solitary cell inside Camp 5, Guantánamo’s maximum security complex. That’s where Dennis Edney met him for the first time. “He was lost,” Edney recalls. They didn’t even speak about his looming court case during that first meeting. “No one had touched him in years,” Edney says, “so I hugged him.”

Outside the wire, there was little public sympathy for Omar Khadr—thanks again to his notorious family. His father had been killed in a 2003 shootout with Pakistani authorities, and Omar’s younger brother, Kareem, had been caught in the crossfire and paralyzed from the waist down. His oldest brother, Abdullah, was facing gun-smuggling charges in the U.S., and his sister, Zaynab, was under investigation by the RCMP. And every time his sister or his mother or his brother opened their mouths—to praise suicide bombers or criticize the country that signed their welfare cheques—Khadr’s case became that much easier to ignore.

“Omar has been branded by the family,” Edney says. “When you talk about the Khadr brand, there is no distinction. But there isn’t an ideological thought in Omar’s brain. I’ve never met a more peaceful guy in my life.”

Stephen Xenakis agrees. A psychiatrist and retired U.S. army brigadier-general, he has spent more than 100 hours speaking with Khadr. “He is a very decent, kind young man—and he has faith,” he told Maclean’s. “We certainly adulate our American POWs who sustain their faith when they are in detention. I don’t think it has radicalized him. There is not a hard edge to him at all, and there is no sense of vengeance.”

Two years ago, Khadr was transferred to Camp 4, a communal section of the prison where detainees sleep in the same room and mingle outside during the day. He spends a lot of time drawing pictures with crayons, but even more time reading. His library list includes the Harry Potter collection, John Grisham novels, Great Expectations and Huckleberry Finn.

Khadr has also been exchanging letters with Arlette Zinck, an English professor at King’s University College in Edmonton. Edney delivers the notes during his visits, sneaking them past the guards in his shoe. “Your letters are like candles very bright in my hardship and darkness,” Khadr wrote in one of his letters. Said another: “About myself, what can I say? We hold on to hope in our hearts and the love from others to us and that keeps us going until we reach our happiness.”

One of the books Zinck recommended was Ishmael Beah’s A Long Way Gone: Memoirs of a Boy Soldier, which tells the story of a 13-year-old who was forced into the Sierra Leone army, ordered to kill, but later rehabilitated. Khadr said he was “struck by the simplicity truthfulness and the straight-from-the-heart” tone of the book. “Children’s hearts are like a sponge that will absorb what is around it, like wet cement, soft until it is sculptured in a certain way,” he wrote. “A child’s soul is a sacred dough that must be shaped in a holy way.”

As far as the U.S. government is concerned—and Sgt. Speer’s widow—Khadr’s soul has been shaped in a way that is anything but holy. Michael Welner, a psychiatrist who testified for the prosecution, said Khadr remains a “highly dangerous” man who is devoted to jihad and will pose an immediate threat as soon as he is released. (It was Welner who said that Khadr has been “marinating” in a community of diehard Islamists.) Tabitha Speer agreed. “He’s a murderer in my eyes and always will be,” she told reporters. “My children are the victims.”

His agreed statement certainly supports that belief. In it, Khadr admits that “if non-believers enter a Muslim country then every Muslim in the world should fight the non-believers.” He admits that he “voluntarily of his own free will chose to conspire and agree with various members of al-Qaeda to train and ultimately conduct operations to kill United States and coalition forces.” And he admits—again—that he tossed that grenade. “Khadr could have left the compound if he wanted,” the document reads. “He chose to stay behind and fight the Americans.”

No matter how many novels he reads or how many pictures he draws, those chilling facts will stay on the public record forever, reminding the world—and the National Parole Board—exactly why he ended up in Guantánamo Bay in the first place.

So, too, will the verdict of a military jury. Although his plea agreement guaranteed a punishment of no higher than eight years, a sentencing hearing was still convened, just in case the panel decided on something less (the jury was not told that about the plea bargain in advance, and their sentence would have only applied if it turned out to be shorter than the agreed eight years).

Symbolic or not, military prosecutors asked for another 25 years behind bars. The jury decided on 40—a full 15 more than even the government wanted. Clearly, the members weren’t convinced that Omar Khadr is safe to walk the streets.

More than 5,000 American service members have been killed in the Iraq and Afghanistan wars. Khadr is the only person to be convicted of murder in connection with any of those deaths.

Tonight, the 24-year-old is back in Camp 5, in a solitary cell where he will count down the days until his flight home to Canada. (Foreign Affairs Minister Lawrence Cannon confirmed that the feds will approve his transfer request next year.) In the meantime, Dennis Edney is preparing for his client’s eventual return to society—which will include welcoming Omar into his own home.

“He will go and visit his family and stay with them, as all kids should do, for a week or two,” he says. “And then he will join me in Edmonton, and we will work on his education and learn to get on with his life. He will be a positive role model.”

But even Edney, a man who has come to love Omar Khadr like a son, understands that the transition will not be smooth. For a person who has spent eight years in shackles, the attention and the publicity will be overwhelming. “I’ve told him that there will be groups wanting to identify with him, to use him for their own needs. And I’ve told him that as much as he thinks he’s strong, they will manipulate him. He needs time to get the strength to stand on his own two feet.”

And to decide—on his own—which direction he is going to walk.