Joshua Boyle, the son of an Ottawa tax court judge, was married for about a year to Zaynab Khadr. Who is the eldest daughter of Ahmed Said Khadr, who was accused by the U.S. and Canada of being an associate and financier for the terrorist group Al-Qaeda. Ahmed Khadr himself studied at the University of Ottawa, and the family moved between Canada, Afghanistan and Pakistan.

Zaynab Khadr was a fierce defender of her family, and this attribute was largelydisplayed when Omar Khadr, her brother was captured as a 15-year-old fighting with the Taliban in Afghanistan and charged with killing an American soldier.

Boyle on the other hand was a principled man by nature “a crusader” said his friend Alex Edwards. It was therefore no surprise when Boyle became captivated by the situation of Omar Khadr, who was being held in a U.S. prison in Guantanamo Bay.

“Here was this kid, this Canadian child, off in an illegal American prison, and everyone in (Canada) was vilifying the Khadr family, and Josh decided, ‘Hey, this isn’t right.’ So he went off and devoted several years of his life to help this innocent kid.” Prior to this, Boyle had no connection to the Khadr family, but introduced himself and volunteered to help them.

Boyle acted as the Khadr family spokesperson in 2008, the same year Zaynab staged a hunger strike to protest her brother’s detention.

A year later, Boyle married Zaynab Khadr. At the time, He was 25, and she 29. This was the third marriage for Zaynab. Her first husband was sought as a conspirator in a bombing of the Egyptian Embassy in Pakistan and Osama Bin Laden was one of the guests at her second wedding in Afghanistan. 

Back in Canada, Zaynab was in the front pages again in 2004 for controversial remarks she made criticizing the way children were raised in Canada. Suggesting that the Sept. 11 terror attacks were justified.

Edwards knew Boyle for over a decade, mainly through an online role-playing Star Wars game. Boyle was a “very private person,” but had a reputation in the gaming world as being both cunning in getting people to do what he wanted and generous to new players, he said.

The marriage didn’t last long, however as they divorced in 2010.

The next year, Boyle was married again to Caitlan Coleman, a U.S. citizen who grew up in rural Stewartstown, Pa. It is reported that the pair met on Star Wars fan sites.

Edwards wrote in a blog post. “What’s even less clear is why they thought this was a good idea. Joshua has a loose connection to Afghanistan, a deep respect for Islam  —  he may even have been in the process of converting  —  and a purely academic interest in terrorism, but none of that even remotely qualifies him to travel safely in Afghanistan. It could have been simple naiveté, but I, and many others, have always known Joshua as an exceptionally cunning and savvy man. Maybe he was overconfident. Maybe he was immature. Maybe this time Joshua just bit off more than he could chew.”