Sheldon Plener shares his best advice on becoming an acclaimed sports lawyer

Sheldon Plener's law career took an unexpected turn when he helped negotiate the NBA's expansion into Toronto, creating the Toronto Raptors. (Photo courtesy of Cassels Brock & Blackwell LLP)

Sheldon Plener didn’t set out to become a sports lawyer. But that’s where his legal journey took him: first, by helping to negotiate the expansion of an NBA team into Toronto in the mid-1990s; then as a key figure in the Ottawa Senators organization, where he’s currently the chairman and governor, after former owner Eugene Melnyk died this past spring. Now, the partner at Cassels Brock & Blackwell finds himself heading up the sale of the NHL team.

While Plener was not at liberty to discuss the sale on this podcast, he still has plenty of stories to share, from his behind-the-scenes access to the birth of the Toronto Raptors to his all-star days with the Toronto Maple Leafs intercounty baseball club. And he explains how he got to where he is, including his biggest tip for any young lawyers hoping for a career in professional sports law.

Elsewhere in the episode, the boys chat about who they’re rooting for at the World Cup (hint: not a lot of European countries with regrettable mid-20th-century histories), and they give props to Denis Shapovalov for helping to secure Canada’s victory at the recently wrapped Davis Cup.


Menschwarmers is hosted by James Hirsh and Gabe Pulver, and produced and edited by Michael Fraiman. Our intro music is by Coby Lipovitch, and our outro music is “Organ Grinder Swing” by chēēZ π. This show is a member of The CJN Podcast Network. Follow the Menschwarmers on Twitter @menschwarmers or TikTok @menschwarmers. To learn how to support the show by subscribing to this podcast, please watch this video.