Sidney Crosby's Agent Wants to See Trade

"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," Brisson said in the article.

Crosby's History with the Penguins and Canadiens

The 37-year-old center his since been named among the greatest NHL players of all time en route to tallying 1,687 points so far with Pittsburgh.

According to Yahoo Sports, NHL insider Greg Wyshynski was responsible back in the summer for the recent spike in the rumor mill surrounding Crosby no longer being a Penguin. Wyshynski said then that there’s reason to believe Crosby could one day be a Canadien.

 “I’ve long believed that Sidney Crosby will end his career in Montreal,” Wyshynski said on a podcast. “If he’s gonna go anywhere and he’s gonna try to do something spectacular, (that’s) being part of the legacy and lineage of the Montreal Canadiens, being part of a team that’s got upward trajectory and have a good chance, maybe (win) a late career championship with a team that hasn’t won since 1993 ... I always assumed if it wasn’t Pittsburgh, it would be Montreal."

While with the Penguins, Crosby has been a six-time All-Star Game participant and was most recently named the captain of Canada’s 4 Nations Face-Off. The Pittsburgh Penguins have additionally qualified for the Stanley Cup Playoffs a whopping 16 times with Sidney Crosby on the team, specifically from 2007 to 2022.

However, he has only hoisted the Stanley Cup three times as captain of the Penguins (which he was named by the time he was only 19 years old), and clearly yearns to do so at least one more time while with either Pittsburgh or the Canadiens.