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The Canadian Security Intelligence Service headquarters in Ottawa on Nov. 5, 2014.Chris Wattie/Reuters

An informant working for the Canadian Security Intelligence Service, who smuggled three British schoolgirls into Syria for the Islamic State in 2015, breached the spy service’s rules that prohibit paid recruits from engaging in illegal activities including human trafficking.

Trafficking people is also an offence under the Canadian Criminal Code and an international protocol on the practice of which Ottawa is a signatory.

Informant Mohammed al-Rashed trafficked the British teens into Syria for Islamic State on Feb. 17, 2015. Britain’s Scotland Yard was frantically searching for the missing teens at the time and was unaware that they had been smuggled into Syria by an operative working for Canada. Ottawa’s relations with Turkey were also damaged by running an operative in the country without its knowledge.

The rules for CSIS operations that were in place in February, 2015, when the trio of underage girls were trafficked, state: “human sources will carry out their tasks on behalf of the Service without engaging in illegal activities.”

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The Ministerial Directions for Operations issued by the Public Safety Minister at that time also said that CSIS must not only observe the rule of law, but that covert operations must consider the impact on ”Canadian foreign-policy interests and objectives.”

Steven Blaney, the Conservative public safety minister at the time the girls were trafficked, told The Globe and Mail that he wasn’t aware of the covert operation and that CSIS should have acted within the law.

Mr. Blaney said he was never asked and did not authorize CSIS to run an operative who was smuggling Islamic State recruits into Syria, including the underaged girls.

“It is sensitive but the truth is the best thing. My office was not aware of that situation,” he said. “We have to act within the law. … I can hardly see how we could have let this happen or authorized it. It is way too dramatic.”

He added: “It is a sad story because they [teenage girls] were trafficked.”

Huda Mukbil, a former senior intelligence officer who ran CSIS agents before she left the agency in 2017, said the spy service should have sought the approval of Mr. Blaney to conduct that type of intelligence operation.

“The source was bringing in foreign fighters, that in itself is an illegal activity, because you are facilitating terrorism,” Ms. Mukbil said. “So everything he was doing, you needed ministerial approval to do. He was conducting illegal activities on behalf of a terrorist organization.”

A heavily redacted Sept. 2015 report by the Security Intelligence Review Committee (SIRC), an oversight body now known as the National Security and Intelligence Review Agency, cited multiple CSIS failings in the handling of human sources working overseas.

The report speaks of a case, which two sources say was the al-Rashed operation, where “CSIS should have notified the minister” and where Canadian diplomats “were insufficiently briefed.” The Globe is not identifying the sources because they were not authorized to discuss national-security issues.

“The temptation to pursue high-value intelligence may have overcome some of the governance and care that should have surrounded such an operation,” said national-security expert Wesley Wark, senior fellow at the Centre for International Governance Innovation. “It was a tantalizing opportunity for CSIS to acquire an inside source on the pipeline that was taking Islamic State recruits into Syria. That was clearly a high-value intelligence target at the time.”

CSIS has declined to confirm or deny whether Mr. al-Rashed worked for the agency. But the government says stronger oversight measures have since been put in place to ensure covert activities comply with Canadian laws and the Charter. CSIS is also now required to inform and get ministerial approval for any “high-risk” activity that could cause a “potential public controversy.”

“I am unable to discuss specifics without putting sensitive operations at risk,” CSIS spokesman Brandon Champagne said. But he added that “robust” accountability measures were enacted for the spy service after the SIRC report.

It was only after Turkish authorities arrested Mr. al-Rashed on Feb. 28, 2015, that CSIS informed the chief of Scotland Yard’s counterterrorism unit that their operative had transported the British teens into Syria, according to The Secret History of the Five Eyes, a new book by author Richard Kerbaj that recounts parts of the informant’s story.

Mr. al-Rashed’s capture threatened to place Canada at the centre of an international incident, after Turkish media reported that he shared the girls’ passport details with CSIS on Feb. 21, 2015, and that he had smuggled other British nationals seeking to join the Islamic State. Turkish media also reported that Mr. al-Rashed told Turkish intelligence that CSIS promised him asylum in Canada.

The Globe has reported that Mr. al-Rashed was freed on Aug. 5 after serving seven years in a Turkish prison on terrorism and smuggling charges, including trafficking the trio of British girls, and that CSIS had planned to relocate him to Canada after his release. The government will not say if he has been granted asylum.

The 2015 arrest strained relations with Turkey. The Globe reported last week that Jeffrey Yaworski, who was at the time CSIS’s deputy director of operations, went to Ankara shortly after Mr. al-Rashed’s detention to press Turkey to keep quiet about CSIS’s role in the operation.

Turkey eventually agreed to Mr. Yaworski’s request, The Globe reported, but punished Canada by limiting the number of CSIS agents operating at the Canadian embassy in Ankara. CSIS also promised that any further clandestine activities should be joint operations.

Around the time Mr. Yaworski was holding secret talks with Turkish authorities, CSIS persuaded British counterterrorism officials to cover up its role in the handling of Mr. al-Rashed, according to discussions revealed in Mr. Kerbaj’s book.

Mr. Yaworski and CSIS declined to discuss the matter.

The SIRC report in 2015 recommended CSIS should no longer rely on Crown immunity as a defence against criminal liability and said the service should consider the impact that covert operations have on Canadian foreign policy.

CSIS has since accepted those recommendations. In 2017, the government created the National Security and Intelligence Review Agency with stronger oversight powers. In 2019, new ministerial directions were approved for CSIS.

Those directions state that all CSIS activities must be “lawful and authorized” and that the service has a duty to inform the public safety minister and his deputy minister of any “high-risk” covert activities. Any potential foreign-policy risk that could harm relations with other countries must also be discussed with Global Affairs, the directions state.

The government also set up an independent intelligence commission with quasi-judicial powers to review all federal intelligence agencies, the RCMP and Canada Border Services Agency.