In 1969, David Milgaard, 16 at the time, was charged and then wrongfully convicted of murder. He was later allowed to claim that Canada conspired with the U.S.in abusing him.
In a similar case, Canadian computer engineer Maher Arar was tortured in a Damascus prison in 2002, after he was transferred there by USA officials based on a Canadian tip-off.
Prominent Canadians, activists and newspaper editorial boards have rallied behind Khadr for several years through public statements, visits to MPs, a parliamentary petition, and a letter writing campaign.
Khadr, 30, pleaded guilty in 2010 to killing a United States soldier in Afghanistan when he was 15, but Canada's Supreme Court later ruled that officials had interrogated him under "oppressive circumstances" such as sleep deprivation.
Khadr, now on bail pending an appeal of his USA conviction, has said he admitted to killing Speer and to the other purported war crimes only as a way out of the infamous prison in Cuba given that he could have been held indefinitely even if acquitted.
The widow of Speer and another American soldier blinded by the grenade in Afghanistan filed a wrongful death and injury lawsuit against Khadr in 2014 fearing he might receive a payout. Khadr's Egyptian-born father was killed in 2003 when a Pakistani military helicopter shelled the house where he was staying with senior al Qaeda operatives.
Former Guantanamo prisoner Omar Khadr (center) is pictured here in 2015 with his lawyer Dennis Edney (left) and Patricia Edney.
Posters used words such as "disgraceful", some called for the Canadian citizen to be kicked out of the country, while others argued the money should go to the family of Chris Speer, the USA special forces soldier Khadr is alleged to have killed in 2002.
Khadr spent a decade in Guantanamo before being returned to Canada in 2012 to serve the rest of his sentence.
After his release, Khadr apologized to the families of the victims and said he rejected violent jihad. He was serving an eight-year sentence, his attorneys said two years ago.
May 28, 2013: Khadr is transferred to the maximum security Edmonton Institution.
April 24, 2015: Alberta judge grants Khadr bail.
The government lost all three cases and, ironically, it was the 2010 Supreme Court decision that may have helped seal the multimillion-dollar deal in this civil case. He can also get rid of his monitoring bracelet.
April 2017: Khadr's official Canadian criminal record contains errors, such as referring to the military commission as "youth court", The Canadian Press reports.
Apologizing is a very Canadian thing to do, but by apologizing and compensating Khadr, we send the wrong message to our allies and to the terrorists we are fighting.