The Toronto Maple Leafs have actively been negotiating with John Tavares and Matthew Kiens. NHL free agency starts at noon eastern on July 1st, which does not give Toronto much more time to negotiate. One insider admitted that he is less confident that Tavares will stay with the Leafs this offseason.

NHL insider Pierre LeBrun wrote on The Athletic that he is skeptical of a John Tavares reunion in Toronto.

LeBrun explained that he is “not as confident” as he has been in the past about a deal getting done.

“Dialogue continues between the Toronto Maple Leafs and John Tavares’ camp, led by agent Pat Brisson. It’s been a grind. But what’s important to note is they’re keeping at it. The dialogue is almost daily. The sides are motivated to find a way to get it done, although the closer next Tuesday gets, the more real the idea of Tavares, 34, dipping his toes becomes. I think it gets done before that happens, but I’m not as confident as I was a week ago.”

LeBrun pointed to recent extensions for Matt Duchene ($4.5 million AAV) and Brock Nelson ($7.5 million AAV) as troublesome for negotiations.

LeBrun noted that Tavares “is willing to take less than market value to stay in Toronto.” But a rising market could make Tavares too expensive for the Leafs to decide to re-sign.

LeBrun does not think John Tavares will accept bargain contract from Leafs

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Tavares will be 35 years old at the start of the 2025-26 NHL season. But that does not mean he's willing to accept more than he's worth on his next contract.

LeBrun previously reported that he thinks it is a “stretch” to imagine Tavares settling for a bargain contract.

“The Leafs and John Tavares’ camp continue to talk and touched base again this week,” LeBrun reported. “There remains mutual interest in getting something done, but finding that sweet spot on a fair deal isn’t quite there yet. The idea that Tavares might sign for a bargain $5 million AAV seems like a stretch to me. It’s going to have to be above that to get it done, given the year he just had, although term is part of the equation as well.”

Big changes could be coming to Toronto this offseason if Tavares does not return. The Leafs are also expected to lose forward Mitch Marner during NHL free agency.

If the Leafs do not have any luck in free agency, they could reinforce the roster through the trade market.