As a foreign correspondent, Gillespie reported extensively from Afghanistan, Iraq, Chechnya and the Russian Caucuses,[1] relaying information on the fall of the Taliban, the dismantling of Saddam Hussein's statue in Baghdad's central square, and the deadly siege of Beslan School Number One.

Born in Melfort, Saskatchewan, Gillespie attained a master's degree in labour history from Memorial University of Newfoundland.

[3] He reported extensively on Canada's intelligence agencies, the Air India Inquiry, the Toronto 18 and Canadian Omar Khadr, and Guantanamo Bay.

[10] In 2013, Gillespie wrote, produced and narrated the influential short documentary "Made in the USA", which investigated the potential impact of Ontario PC leader Tim Hudak's policy proposal to introduce American style, anti-union right-to-work laws to Canada.

[11] Labour leaders in Ontario have credited the film for playing a significant role in convincing Mr. Hudak to suddenly reverse himself and drop the policy.

Gillespie followed "Made in the USA" with a sequel released in May 2014, called "Hudak's Plan B", an exploration of how Wisconsin governor Scott Walker neutered the state's public sector unions without a right-to-work law.

[15] Gillespie is the author of a book entitled, A Class Act: An Illustrated History of the Labour Movement in Newfoundland and Labrador.

In 2011, Gillespie and colleagues were nominated for the Canadian Association of Journalists 2010 award, for the story "Pakistan International Airline Threat", which aired on CBC News' The National.