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Why Sidney Crosby's Latest Speculation Could Quietly Matter to the Maple Leafs


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Austin Kelly
September 10, 2025  (0:08)
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Mar 2, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Penguins center Sidney Crosby (87) moves the puck ahead of Toronto Maple Leafs center Auston Matthews (34) during the second period at PPG Paints Arena
Photo credit: Charles LeClaire-Imagn Images

Recent comments by Sidney Crosby's agent Pat Brisson has created new intrigue over the Penguins forwards future as things start changing in Pittsburgh.

New comments from Crosby's agent, Pat Brisson of CAA Sports, has expressed clarity on where Crosby stands as a potential free agent with rumors of his future in Pittsburgh bint uncertain.
Brisson tells 'The Athletic' that the goal is still for Crosby to win a cup, and the hope is that Pittsburgh has a strong season to quiet questions over a potential split.
Well, it's a reality. First of all, he's been so consistent for 20 years. He had another great year last season. He just keeps going. The comparison is Tom Brady. We want Sidney to hopefully be in the playoffs every year. We want him to hopefully win another Cup or two.

So each year the team that he's playing for fails to make the playoffs, it creates a lot of speculation. In reality, he's not getting any younger.

We're here to support him. It's the beginning of the season here. Let's see how things are going. Hopefully they have a great season and the speculation will go away.

How Sidney Crosby's Situation Could Quietly Influence the Maple Leafs' Strategy

Pat Brisson's comments do little in changing the narrative of at least openness that Sidney Crosby could play out his NHL career outside of Pittsburgh.
The goal is ultimately to win, and Crosby may not be done in wanting to do so. Having already won everything he needs to, the hunger still exists to win, and it could play favorably into the hands of the some of the league's top contenders, including Toronto.
The Leafs didn't use the departure of Mitch Marner to add a big name acquisition this offseason, and could set them up to add a major piece next offseason instead, and Crosby is just one of the names out on the rumor mill.
If the Pittsburgh Penguins do indeed struggle and miss the playoffs as they did last season, it'll open the talks of Crosby's potential exit even further, and the chance of a possible full rebuild.

Why Maple Leafs Fans Are Watching the Crosby Storyline Closely

The Toronto Maple Leafs have poised themselves to nab a top free agent option in the 2026 offseason, and Crosby could be one of the many names that attract Toronto.
A player like Crosby would be a dominant mentor on the Leafs, and fill the 2C spot and allow John Tavares the chance to move onto the wing.
It's highly unlikely Crosby would sign with the Leafs, however, but nothing seems certain although the likeliest option would be Crosby finishing out the rest of his career with the Pittsburgh Penguins.
Crosby has little reason to chase a Stanley Cup, having already won three, and has done enough in his career to choose to settle down as a one-team man, even if it's not with a winner.
If Crosby were to stay in Pittsburgh and the team struggle, and have the first pick, Crosby could be a potential mentor to Gavin McKenna, much like Mario Lemieux was to Sid in his first season in Pittsburgh.
It won't stop fans from dreaming, however. Leafs fans have hoped to have a top player eventually join Toronto in the near future, and while the big fish is Connor McDavid, Crosby has still shown himself to be one of the league's best even at the stage in which he has now found himself as one of it's elder statesmen.
More likely destinations have included the Montreal Canadiens, in which Crosby grew up idolizing and could use a #1 center like Crosby in their lineup, as well as the Colorado Avalanche in which he would be reunited with fellow Cole Harbour native Nathan MacKinnon.
One team that hasn't been talked about but could be one to watch is the Vegas Golden Knights.
Vegas has shown their willingness to spend having acquired Mitch Marner this offseason from Toronto, and has impact players in Jack Eichel and Mark Stone.
One player who may be the most intriguing on the Vegas roster who's not an established player but important as a target in Brendan Brisson, the son of Pat Brisson, Crosby's agent.
Just because Crosby is nearing the end of his career, that doesn't mean he still can't be a quality playoff contributor. Brad Marchand was one of Florida's top producers en route to their recent Cup win at the age of 36.
The Detroit Red Wings were led by 37-year-old Steve Yzerman to a Stanley Cup in 2002. Age doesn't always keep away a champion.
Although a proven winner like Crosby, even at the tail end of his career, could still be the type of proven leadership that the Toronto Maple Leafs may want to get them to a Stanley Cup finals.
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Why Sidney Crosby's Latest Speculation Could Quietly Matter to the Maple Leafs

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