Risky 2-Time Stanley Cup Championship Goalie Linked to Maple Leafs

On the latest episode of 32 Thoughts, the podcast, Elliotte Friedman wondered if Sergei Bobrovsky could end up in Toronto. Noting that there are links between the Florida Panthers two-time Stanley Cup-winning goalie and the Maple Leafs, Friedman says that Leafs GM John Chayka is sitting on one or two other moves that would change his team.

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Bobrovsky is reportedly seeking a six-year deal worth $42 million at age 37. The Panthers would like to re-sign him, but they may be ready to turn the page if his ask doesn’t come down. It sounds like Bobrovsky wants the contract Brad Marchand got after his arrival from the Boston Bruins.

The argument against is that goalies age differently than forwards, Bobrovsky had a bad season in 2025-26 and if the Panthers are going to invest term and money into someone, they don’t want it to be a netminder, who’s game could be on the verge of falling off a cliff.

It would be different if he wanted to do a one-year, show-me kind of deal to prove his game is back and he’s worth more money, that would be one thing. Does that lead to him going to Toronto? It seems like a stretch, even though they do have the cap space to pay him well on a one-year contract.

They’d also be moving out one of Anthony Stolarz or Dennis Hildeby to make room for him. Perhaps it’s Hildeby, as Stolarz won a Cup as Bobrovsky’s backup in Florida. “About Bobrovsky, it wouldn’t shock me if he ended up being their guy, potentially.”

Florida can and probably will spend $5-$6m on a starting goalie. Whether that is Bobrovsky, or a name like Jordan Binnington remains to be seen. There was some chatter linking Connor Hellebuyck to the Panthers, but unless they pull off a miracle, he is out. Following the Brady Tkachuk trade, Florida has little to offer now that it traded all their first-rounders.

That leaves Bobrovsky with a decision to make. Stay for less in Florida or test the market and show the Panthers they were wrong. Would he be willing to do the latter in Toronto? If so, then he might also be willing to do the same in a place like Edmonton.

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