[2] Matheson had an intention to follow the footsteps of his father, Jack, a long-time sports editor for the Winnipeg Tribune.
He graduated from the University of Manitoba with a degree in political science, and while in school, worked a part-time night shift with the Tribune.
[1] He got his first job upon completing school with the Regina Leader-Post, but moved west to Edmonton, Alberta six months later.
In addition to writing, Matheson also was a part of the CFRN radio broadcasting team that covered the Oilers.
[1] In January 2022, Matheson became a subject of international sports news after a heated exchange with Oilers player Leon Draisaitl after the team's sixth straight loss, calling Draisaitl "pissy" and accusing him of not providing the kind of answers he wanted for his column.