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Sergei Bobrovsky is one of the Leafs' biggest gambles of all-time

The Toronto Maple Leafs have made their fair share of gambles in net, but the newest one is the biggest.
Apr 4, 2026; Pittsburgh, Pennsylvania, USA; Florida Panthers goalie Sergei Bobrovsky (72) pokes at the puck against Pittsburgh Penguins center Sidney Crosby (87) during the first period at PPG Paints Arena. Mandatory Credit: Mark Alberti-Imagn Images
Apr 4, 2026; Pittsburgh, Pennsylvania, USA; Florida Panthers goalie Sergei Bobrovsky (72) pokes at the puck against Pittsburgh Penguins center Sidney Crosby (87) during the first period at PPG Paints Arena. Mandatory Credit: Mark Alberti-Imagn Images | IMAGN IMAGES via Reuters Connect

For years, the Toronto Maple Leafs have lacked a true No. 1 goalie. Someone that they can put in between the pipes and rely on to put in quality outings. It is one of the biggest reasons why the "Core Four" era in Toronto did not work out.

Because of that, one of John Chayka's first moves was to fix that problem. He did so by signing Sergei Bobrovsky to a three-year deal at the start of free agency. While this move could solve the goaltending problem, it's a risky one. It will go down as one of the biggest gambles in Leafs history.

How Sergei Bobrovsky stacks up against other gambles the Leafs made

Bobrovsky is coming off one of the worst seasons in his career. In 54 games, he had a 3.07 goals-against average and a .877 save percentage. It is the worst save percentage of his career. While he struggled last season, he was one of the core pieces of a Panthers squad that won back-to-back Stanley Cups. The hope is that he can go back to that player. The guy who had a save percentage around .905 and a goals-against average under three.

But there is no guarantee that Bobrovsky can return to that level of play. Sure, down years happen with everyone, and we have seen plenty of players rebound after a down season. But it normally does not happen when a player is 38 years old. These struggles may not be just a down season. It could be a sign that he is starting to decline. That he will never be able to go back to the player he was, and it's all downhill from here.

If he struggles, it will be just as bad as the time the Leafs gambled on David Clarkson. The Leafs signed Clarkson to a seven-year deal back in 2013. While he averaged around 20 points per season, the hope was he could build off his 2012-13 season, where he logged 46 points. While he was a season removed, they bet he could rediscover it. But this blew up in their faces as he suited up in only 118 games for the Leafs, recording a measly 26 points.

It would also not be the first time that the Leafs have gambled on a netminder. Back in 2007, they traded for Vesa Toskala in hopes that he could go back to the player he was before the 2004-05 lockout. However, that would not be the case, as Toskala struggled for most of his two-and-a-half-year tenure with the club. He had an average goals-against of 3.08 and a .894 save percentage in 145 games. Nowhere near what they hoped he could do.

The Leafs understand the risk they are taking on by bringing in Bobrovsky. He is even riskier, as his not working out will be the defining move of Chayka's tenure and set the franchise back years.

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