Steve Simmons on Leafs’ Lottery Win & His VIRAL Press Conference Moment

Nick Alberga & Jay Rosehill are joined by Toronto Sun columnist Steve Simmons to break down a huge moment for the Maple Leafs.

Simmons reacts to Toronto winning the draft lottery, calling it a “fantastic” boost for a team and fanbase that badly needed some good news. He explains the significance of landing the No. 1 overall pick, how it adds a premium piece to the organization, and why it’s “manna from heaven” for John Chayka and Mats Sundin as they begin their tenure.

He also addresses his viral question at the Chayka-Sundin introductory press conference—why he asked it, what he was trying to accomplish, and why he might handle it differently in hindsight. Plus, Simmons gives an honest look at the media business, admitting his job is about getting reads and sparking conversation, while sharing the tense tone he felt throughout the presser.

The conversation continues with thoughts on Sundin’s role moving forward, Simmons’ relationship with MLSE CEO Keith Pelley, and how he sees things operating behind the scenes with this new leadership group.

Finally, he weighs in on Auston Matthews’ future with the franchise.

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