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The Toronto Maple Leafs could have another blockbuster signing in the works, as the organization looks to get back into contention.

If Toronto Maple Leafs fans thought that GM John Chayka was ready to play golf after signing Darren Raddysh, they might have another thing coming.

While the Joseph Woll trade and Raddysh signing were major developments, and seemingly bigger ones could be on the horizon.

According to insider Elliotte Friedman, the Leafs could have their sights set on impending UFA goaltender Sergei Bobrovsky.

During Monday’s edition of the 32 Thoughts Podcast, Friedman discussed the next steps for the two-time Stanley Cup winner. In his estimation, the Florida Panthers aren’t overly keen on signing Bobrovsky at the price point he wishes.

In particular, the chatter posits that Bobrovsky is looking for a six-year deal worth around $42 million. That’s something the Panthers apparently aren’t willing to do. And it pretty much shuts the door on the Russian netminder returning to Florida.

But that price point might not preclude the Maple Leafs from making something happen. Even after adding Raddysh’s cap hit to the books, the Leafs have nearly $19 million in cap space. Even at his desired cap hit, Toronto could fit Bobrovsky under the cap and have some space left over to do something else.

Maple Leafs Have 2 Interesting Connections to Bobrovsky

Friedman made another interesting point regarding why Bobrovsky actually makes sense for the Toronto Maple Leafs. The notable insider pointed out the relationship between Bobrovsky and current Toronto goalie Anthony Stolarz, one that dates to Stolarz’s days in Florida.

Stolarz backed up Bobrovsky during Florida’s 2024 Stanley Cup run. While Stolarz saw action for about two periods during the entire run, the relationship between both goalies remains strong.

As such, Friedman’s comments hint at the Maple Leafs recreating the Panthers’ goalie tandem, with Stolarz presumably returning to a backup role under Bobrovsky, the starter.

If that’s the plan, the Maple Leafs could certainly do worse. While Bobrovsky would be 38 heading into this season, he could easily be the best goalie Toronto has had in a long time.

But there’s one other connection. Steven Lorentz, another former Panther the Leafs signed in free agency, also has a good relationship with Bobrovsky. In particular, Lorentz was the Russian goalie’s preferred shooter during practice.

As Friedman put it, Bobrovsky was the reason Lorentz remained in the NHL, as he requested the team to keep him around.

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Does Toronto Have Realistic Chance at Bobrovsky?

So, the question begs: Do the Maple Leafs have a realistic chance at signing Bobrovsky?

On the surface, yes. The Leafs look like they’re getting ready to get back into the playoff race. Despite the mixed reactions to Raddysh, he gives the Maple Leafs blue line and power play a different look.

The addition of another puck-moving blueliner in Emil Andrae, plus Gavin McKenna, presumably, makes the Leafs an attractive team. And especially if the Panthers are unwilling to re-sign him, there’s no reason why the Maple Leafs wouldn’t take a chance on paying Bobrovsky what he wants.

It wouldn’t matter if the deal were even an eight-year max-term contract. The point is to win in the next two to three seasons. So, the back end of the contract ultimately doesn’t matter. If the Maple Leafs win a cup in that interim, no one will really care if the organization signs Bobrovsky for 200 years.