FALLS CHURCH, Va. (AP) — A Canadian citizen who led propaganda efforts for the Islamic State group and personally executed two Syrian soldiers in widely circulated videos was sentenced to life in prison Friday by a U.S. judge.

Prosecutors sought the life sentence for Mohammed Khalifa, 39, a Saudi-born Canadian who held prominent roles for the Islamic State group from 2013 until his capture in 2019.

In a sentencing memorandum, prosecutors said Khalifa played a key role in the group’s successful efforts to recruit tens of thousands of foreign fighters to defend its self-proclaimed caliphate in Iraq and Syria.

In two notorious propaganda videos titled “Flames of War,” Khalifa can be seen shooting Syrian soldiers in the back of the head after they dug their own graves. He also narrated the videos.

Khalifa’s defense attorneys had sought a term of just 20 years at Friday’s sentencing hearing in Alexandria, Virginia. They argued that he was less culpable than two British-born Islamic State members — Alexanda Kotey and El Shafee Elsheikh, nicknamed the “Beatles” by their captives — who personally beat and tortured Western hostages. Both Kotey and Elsheikh were convicted in Alexandria — one has received a life sentence and the other is expected to get life when he is formally sentenced next month.

They also argued that it’s wrong for the U.S. to impose such a severe sentence against a Canadian who was not convicted of directly killing or harming any Americans and could have just as easily been extradited to Canada.

Khalifa pleaded guilty last year to terrorism charges. In a letter to U.S. District Judge T.S. Ellis written ahead of Friday’s sentencing hearing in Alexandria, Virginia, Khalifa said he felt compelled to help the Syrian people in their revolt against dictator Bashar al-Assad, but that he made a mistake by opting to become a fighter as opposed to joining an aid organization.

“As I followed the events in Syria, I became disgusted with myself for sitting by and not doing something,” he wrote.

According to an FBI affidavit, Khalifa told FBI agents he expected to be sent to an IS training camp when he joined the organization in late 2013. Instead, he was recruited to join the organization’s media department because of his English language skills and spent nearly five years as a leader in their propaganda unit.

Khalifa told agents he was captured in January 2019 when he defied an IS order to flee from advancing forces. Instead, he said, he launched a solo attack of sorts on Syrian Defense Forces, surrendering after his AK-47 rifle jammed.

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