Since the 9/11 terrorist attacks, Khadrs have been fixtures in the courts, with members of Canada's so-called "al-Qaeda family" frequently arguing that their rights as Canadian citizens trump the national-security measures used against them.
Rulings in these and other cases have prompted complaints from Canada's spies that a "judicial jihad" is fettering their ability to collect potential life-saving intelligence.
"Over the last few years ... our employees have spent too much of their time thinking about where we stand rather than what the bad guys are up to," CSIS director Richard Fadden said in a speech last year. He added that "ideas, money, products and people - they all move. CSIS therefore has to be more mobile to defend Canada against threats."
Yet spies are finding out that the constraints imposed by the Charter of Rights and Freedoms can travel outside the country's borders.
CSIS, once a stay-at-home spy service, is increasingly getting out into the world to collect foreign intelligence. Much of the information is classified, but it's no secret that some practices have proven problematic: judges are increasingly second-guessing interviews of Canadian "targets" in overseas prisons.
The Supreme Court ruled yesterday that CSIS should have been more sensitive to the rights of Omar Khadr, who as a teenager was captured in Afghanistan in 2002. The Pentagon routed him to the U.S. Guantanamo Bay prison camp, where he remains.
"Canada's active participation in what was at the time an illegal regime has contributed and continues to contribute to Mr. Khadr's current detention," the country's top judges said. While the Supreme Court did not order Canada to ask the United States to return him, it stressed that CSIS's actions in the case "did not conform to the principals of fundamental justice."
The Supreme Court is deciding whether to hear a similar case, involving non-Canadian al-Qaeda suspects who were also interviewed by CSIS in the prison.
Meanwhile, an Ontario court continues to wrestle with the rights ramifications of the U.S. extradition case against Mr. Khadr's elder brother, Abdullah, who was interviewed by the Mounties and CSIS while he was held incommunicado in a Pakistan safe-house.
The Khadr family left Ottawa for Afghanistan nearly 20 years ago, to live in the same mud-walled compound as Osama bin Laden.
Before he was killed by the Pakistan army, Omar Khadr's father inculcated his Canadian sons in the Islamist totalitarianism that dominated late-1990s Afghanistan. Omar Khadr was captured in a firefight with U.S. Forces in 2002.