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When Omar was a toddler, his father quit a job as an engineer and moved the family to Peshawar, Pakistan, to join thousands of other radical Muslims, including Osama bin Laden, in the battle against the Soviets. Once there, Ahmed took charge of a Canadian charity that allegedly funneled money to Al-Qaeda. He also ran schools for children who were reportedly taught a radical version of Islam.
In 1992, Ahmed stepped on a land mine and was injured so badly that he was evacuated to Toronto. For a time, the family lived off donations from area mosques, eventually squeezing into a humble flat in a rundown rooming house in the city's west end.
Omar was still in many ways a regular kid. He loved Nintendo, the Bruce Willis movie Die Hard, and junk food. He played basketball and cricket in an alley with his brothers and friends from the local mosque. He could also be a cutup: His sister Zaynab told the Toronto National Post he often impersonated Captain Haddock, the stuttering character from the Belgian comic-book series Tintin. "Buh-buh-billions of bl-bl-blistering bl-bl-blue barnacles!" he would say. "Ten thousand thuh-thuh-thundering typhoons."
Around his father, Omar was different, always bowing his head as a show of respect.
By 1993, Ahmed had healed sufficiently to return with his family to Pakistan. Not long after arriving, the elder Khadr allegedly began plotting with Ayman al-Zawahiri, Osama bin Laden's right-hand man, to blow up the Egyptian embassy in Islamabad. The November 19, 1995, bombing killed 16 and wounded 60. Ahmed was arrested and sent to prison. He went on a hunger strike, protesting his innocence, and was transferred to a hospital in Islamabad. Omar, who was 9 at the time, didn't leave his father's side, often sleeping under the man's bed on the concrete floor.
But the Canadian government lobbied for Ahmed's release, and soon the family was living in Afghanistan with Osama bin Laden. Not yet 12, Omar joined two of his older brothers at an Al-Qaeda training camp, where they were taught to fire Kalashnikovs and build bombs. "[We learned] why we are fighting America ... why being a suicide bomber is an honor, why it's a right religiously," Omar's brother Abdurahman told CNN.
The Pentagon claims to have surveillance video that shows Omar planting a bomb on a road frequently traveled by U.S. troops. "That kid became radicalized," Khadr's former imam says. "It's impossible to go through the experiences he went through and not be affected by them."
When Khadr was captured in the July 2002 firefight that wounded Layne Morris, he was near death. Medics rushed him to the Bagram Air Base in Afghanistan; a few months later, he was dressed in an orange jumpsuit, hogtied, and placed on a C-130 transport headed for Guantánamo. He arrived shackled and hooded, unsure of where he was. "Welcome to Israel," a guard told him.
From the air, Guantánamo Bay is a shimmering body of water knifing toward a jagged ridge of bluish hills on the rugged southern coast of Cuba. The U.S. naval base is 45 square miles of unsettling paradoxes. For more than a century, since the days of Theodore Roosevelt, the United States has held this fortress under an indefinite lease in the dominion of its sworn enemy. The place served as a refueling station during World War II and was a potential target during the Cuban Missile Crisis. In 1995, when Fidel Castro encouraged discontented Cubans to leave, thousands were warehoused here before entering the United States.
The Bush administration began using it as a 21st-century gulag in January 2002, just four months after the 9/11 attacks. The first camp, called X-Ray for its coordinates on a military map, is now in decay, surrounded by razor wire. It sits in a remote, low-lying valley, a rusting ring of cages covered with weeds and vines. Half a dozen hastily built plywood interrogation rooms stand nearby, the site of some of Guantánamo's earliest atrocities.
The heart of the naval base provides a stark contrast. Officers live in brand-new townhouses on winding streets that wouldn't be out of place in suburban Las Vegas. They eat lunch at McDonald's and Taco Bell, and drink Red Stripe beer at a bar tended by cheerful Jamaicans in floral print shirts. Suntanned lawyers spend afternoons playing on the base's Frisbee golf course and puffing on cigars.
"I would bet my boots that when the American public thinks of Guantánamo, they think of these pumped-up Taliban warriors," says Khadr's lawyer, Dennis Edney. "In reality, in the first few years Omar was there, it was a house of horrors. It was a place where Omar was taken from death and back."
Omar Khadr's arrival at Guantánamo in October 2002 coincided with a fundamental shift in the War on Terror. In the 10 months the camp had been open to "unlawful enemy combatants," the military had learned little about Al-Qaeda's inner workings. So officers began employing techniques that included sensory deprivation, waterboarding, and humiliation.
Shortly after his arrival, Khadr was taken to an interrogation room, where his arms were pulled behind his back and cuffed to his legs, straining his limbs from their sockets until he was near delirium, according to the boy's affidavit. He claims he was then forced onto his knees with his wrists cuffed to his ankles. This lasted so long that the 16-year-old urinated on himself. When the military police returned, he contends, they doused him with Pine-Sol and used him as a human mop to clean up the mess. He was then carried back to his cell, where he was left for two days.