The exact timeline is still sketchy, but at some point in the coming weeks, a blindfolded Omar Khadr will be escorted out of his jail cell, shackled at the wrists and ankles, and carried onto a military cargo plane. Though he won’t have the pleasure of witnessing it with his own eyes, Guantánamo Bay, Cuba—Khadr’s prison for the past seven years, beginning at the tender age of 16—will disappear into the distance within a matter of minutes.

Where he will land is still a mystery. The White House announced last week that the 23-year-old is slated to face a military commission—somewhere on U.S. soil—for his alleged war crimes, including the murder of an American soldier in Afghanistan. Yet in the very same breath, Barack Obama’s attorney general left open the possibility that Khadr, a Canadian citizen, could be transferred to his home country before a trial ever begins. Fuelling such speculation is a separate hearing in front of the Supreme Court of Canada, which must decide, once and for all, whether Stephen Harper should be forced to at least ask the Americans to repatriate Khadr. The legal arguments are complex, but at the heart of the case is a growing sense that if the Prime Minister simply asked for his release, Washington would happily oblige.

In other words, that plane leaving Gitmo could fly straight to Canada.

It’s not quite that simple, of course. The Supreme Court may not issue a ruling until the new year, and even if it does order Harper to bite his lip and lobby for Khadr, there is no guarantee the Americans will hand him over carte blanche. But for a boy (now man) who has grown up inside Gitmo’s barbed wire, the end has never felt so close. Which means the biggest question of all—the one Harper is fighting in court to avoid—must now be answered: if Omar does return to Canada, what exactly do we do with him?

“I’m not going to argue that he hasn’t served enough time, but I might argue that he’s still a threat,” says Layne Morris, a retired U.S. army sergeant who lost his right eye in the 2002 firefight that ended with Khadr’s capture. “It comes down to security. Are we confident we can let this guy go and he’s not going to try to cut people’s throats next week? That’s the overwhelming question.”

There is no easy answer. To many, Khadr is still the loyal son of a senior al-Qaeda operative, a Toronto-born teenager who lived with Osama bin Laden and allegedly tossed a grenade that killed Sgt. 1st Class Christopher Speer, a decorated Special Forces medic. To others, he is an innocent child soldier thrust into battle by his radical dad and tortured, over and over, until he confessed to a crime he didn’t commit. It’s no wonder the feds would rather let someone else (i.e., the Americans) figure out which label fits best.

If he is flown back to Canada, Khadr could—at least theoretically—face a bevy of criminal charges, including high treason (“waging war” against an army allied with Canada) and participation in a terrorist organization (al-Qaeda). But would a jury ever convict someone who was shot by U.S. troops at age 15, shipped to the world’s most notorious prison at 16, and who was clearly under the spell of his fundamentalist father? Even with a guilty verdict, it’s hard to imagine his young age would warrant a sentence other than time served.

The other option—allowing Khadr to reunite with his extremist family, where he is sure to become a folk hero for wannabe jihadists—is equally unattractive. His sister once wished she had “the guts” to be a suicide bomber, his eldest brother is an accused al-Qaeda gunrunner, and another brother is paralyzed from the waist down after being shot by Pakistani troops in the same clash that killed their father. The Cleavers they are not.

“Omar has been branded by the family,” says Dennis Edney, that family’s long-time lawyer. “When you talk about the Khadr brand, there is no distinction. But I have talked to Omar about not going back to his family, and Omar understands that and has agreed to that—and his family has agreed to that.” (Members of the family did not respond to emails from Maclean’s.)

Earlier this year, Edney released a so-called “reintegration plan” for his client that includes religious and psychological counselling, supervision by law enforcement officials, and a home-schooling program delivered by King’s University College in Edmonton. “I would take him home with me, in Alberta,” Edney says. “He’s just a kid who wants to be a doctor and who wants to just get on with his life. I’ve never met a more peaceful guy.”

It’s a difficult description to swallow; fellow Canadians have seen the infamous video of a young Omar smiling as he wires together land mines destined for the feet of coalition soldiers. Stephen Xenakis, a U.S. psychiatrist who has treated Khadr over the past year, has his own opinions about whether his patient is still a threat to society. And although he would prefer to save those opinions for a possible day in court, he does offer this much: “He is a really kind, decent, thoughtful, sensitive young man, and he cares about people. It’s really important to appreciate that he does not have any vindictiveness in his nature at all. There is not a hard edge to him at all, and there is no sense of vengeance.”

What Khadr wants, Xenakis says, is “fair justice.” Speer’s widow and two young children crave the very same thing.