[4] When he graduated with a Bachelor of Arts degree in 1931, Canada was in the midst of the Great Depression and the only work he could find was at Eaton's selling hats.
[3] While working at Eaton's department store, O'Brien came in contact with sports editor Jimmy McDonagh, who hired him to cover amateur baseball games for the Montreal Standard.
During his first game, a riot broke out over an umpire's call, and O'Brien's coverage of the event appeared on the front page of the paper the following day.
[2] As a sports editor for the Standard, covering hockey, O'Brien was sued by Detroit Red Wings defenceman Jack Stewart for libel after calling him a "ruffian".
[5] While working for the Montreal Star, O'Brien was sent to cover the 1954 British Empire and Commonwealth Games, specifically the "Miracle Mile" between Roger Bannister and John Landy.