The Dallas Stars have all the pieces to be a true Stanley Cup contender; their appearance in the Western Conference Final for three years in a row highlights the team's ability to make a deep run in the playoffs. They have top-level goaltending in Jake Oettinger, a captain in Jamie Benn that bleeds green, offensive production from the squad as a whole (all but one active player had at least one point in the playoffs), and good defense (needs a little work). Two skaters from Dallas ranked in the top-three in blocked shots this postseason; defensemen Esa Lindell and Thomas Harley had 44 and 39 blocked shots, respectively. Kudos to them, that hurts.
The issue is though, they keep falling short. The Edmonton Oilers proved to be too tough of an opponent again, closing out the series convincingly in five games. Although the Stars were eliminated prior to making a Stanley Cup Final appearance, was this Jamie Benn's potential last, best chance at winning it all? The Stars captain, who was drafted in 2007 by Dallas, is an unrestricted free agent and his future is unknown.
Unfortunately, I really think this run was Benn's greatest potential shot at a Cup. Third time's a charm, right? Not this time.
Jamie Benn's history with the Stars
Benn is the second player in Dallas Stars/Minnesota North Stars history to hit the 1,000-game mark, behind Mike Modano, who played in 1,459. He is the longest-serving captain in the history of the franchise, he's had this honor since 2013. Benn won the Art Ross Trophy in 2015 as the league's leading scorer, the only time a member of the Stars achieved this offensive accolade. He ranks second all-time in goals (399) and points (956) and third in assists (557) and short-handed goals (16) in the franchise's history.
He is a tried and true member of this team and he wants it to stay this way. Benn just finished his eight-year, $76 million contract that he signed in 2016 and is now a UFA. Will he hit free agency on July 1 or will June be a deciding month where they can get a deal done?
Jamie Benn on his future in Dallas: “I don’t see myself going anywhere else. This is all I know.”#TexasHockey pic.twitter.com/Nif8L3RwHG
— Victory+ (@victoryplustv) May 31, 2025
Was this really Jamie Benn's last chance at a Cup?
The 35-year-old was the last member of the Stars to step off the ice post-handshake line with the Oilers after their WCF loss. Was he thinking that this could have been his last, best chance at a Cup and it's now gone? We won't know the answer to this, but we do know that there's a lot of moving parts at play here.
The Stars have young talent signed to long-term deals; defender Miro Heiskanen (8 years, $67.6 million in July 2021), forward Mikko Rantanen (8 years, $96 million starting in the 2025-26 season), and Oettinger (8 years, $66 million starting in the 2025-26 season), to name a few.
We know that Benn is getting older, and slightly less productive, so where does that leave him in the line-up? Do the Stars and their needs have the space for Benn and his needs? Stars general manager Jim Nill, who has won the NHL's General Manager of the Year award twice in a row and is a finalist again for a potential three-peat this season, has a lot to think about with his roster; the roster as a whole and his roster in regards to his captain. Where will Benn be next season?
Every NHL player wants to hoist the Cup, but they do say this is the hardest trophy to win in sports. We never know what the future can bring, but the Stars and Benn didn't capitalize when they had the chance to make it to the the Stanley Cup Finals; then it's just one more round of a best-of-seven series to win the Cup. They fell short three years in a row, so that doesn't give me confidence that this can get done in Dallas in the near future.
If Benn ends up on a different team to finish his NHL career, I hope he is able to get the experience of winning a Stanley Cup, he's so deserving of this accomplishment. It's just that the past doesn't give me confidence of this happening, regardless of the team that he is on. I truly hope that I am wrong, I'm rooting for Benn to win the big one!