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Landsberg started his national career in 1984 as an anchor on TSN's SportsDesk, broadcasting more than 5,000 episodes. Landsberg has covered Canadian college football, horse racing, and figure skating at the 1988 Winter Olympics in Calgary. He also hosted the network's highly acclaimed coverage of the Dubin Inquiry.
In 1997, he received his own show on the network, Off The Record, which is a talk show on current sports news. He continues to host the show after 17 years. He is a regular guest on the TSN Radio 1050 show Macko and Cauz, where he is referred to as the Darcy Tucker/Leo Komarov of radio, in a segment dubbed "the fastest half-hour in sports radio".
Landsberg suffers from generalized anxiety disorder and depression. Landsberg is a supporter for mental health awareness and is trying to popularize the hashtag #sicknotweak in tribute to his mental illness.
Landsberg is Jewish.