Kennedy served in the Canadian military for thirteen years. In a radio interview with VCOM, Kennedy’s mother claimed that he was part of a naval mission to the Gulf of Aden, where numerous nations have deployed warships to combat Somali pirates. In March 2016, Kennedy left the Canadian military and a few months later traveled to Northern Syria to join Kurdish fighters combating Daesh. He would later continue to fight in Nineveh, an Iraqi province sandwiched between Syria and Iraqi Kurdistan.
The Canadian military serviceman was fighting alongside the People’s Protection Units (YPG,) a Kurdish militia force based out of Northern Syria that has extended into Iraq in recent years. AP reports that Turkey considers the YPG to be a wing of the Kurdistan Worker’s Party (PKK), a left-wing political party that has waged a bitter war of independence against Turkey since the 1980’s. This claim on Turkey’s part has proved problematic for the West, as the PKK is considered by NATO to be a terrorist group. The YPG is also a backbone to coalition efforts to defeat Daesh, and are actively armed by the United States.
The most likely explanation for Kennedy’s arrest is that he is associated with a rival faction to the territory he was passing through: the Kurdistan Democratic Party (KDP,) who control the government of Iraqi Kurdistan. They have worked closely with the Turks in the past. A similar incident to Kennedy's arrest occurred in October 2015, when six Western volunteers with the YPG were detained by the KDP. Three others met the same fate in April 2016. However, these nine were all detained because their visas had expired. Kennedy’s mother told VOCM that she is positive her son’s visa was valid through January, suggesting an extra wrinkle to the story.
The Globe and Mail reports that Global Affairs Canada (GAC), which manages Canada’s diplomatic and consular efforts, is aware of Kennedy’s detention and are working to have him released from custody and returned to Canada. Specific details about the incident have been withheld due to "privacy concerns," according to GAC, who also confirmed that he has met with Canadian embassy officials and is in good health.