Which NHL teams with the league's longest playoff droughts are closest to being a Stanley Cup contender?
After the Buffalo Sabres broke their 14-year playoff drought this past season, that leaves us with a new team leading the drought department, that being Steve Yzerman and the Detroit Red Wings, who haven’t seen the post-season since 2016.
Three other teams have missed at least the last five playoffs, those being: The San Jose Sharks (seven), the Chicago Blackhawks (six), and the Columbus Blue Jackets (six).
Which one of these powerhouses is closest to truly being a cup contender, and which ones still have a while to go?
Detroit Red Wings
Alex Debrincat played his third season with the Red Wings this past year, tying his career-high in goals with 41, while setting a new career-high in assists, 44, and points, 85. Despite his personal success, the team failed to make the playoffs, and now, captain Dylan Larkin has requested a trade.
The contending teams that will want Larkin likely won’t want to give up current roster players, so it’s looking like this drought will continue.
Moritz Seider and Simon Edvinsson have become one of the best defensive pairs in the league.
If the team can build around them, as well as the abundance of young talent like Lucas Raymond, Emmitt Finnie, Nate Danielson, and two very solid young goalies in Sebastian Cossa and Trey Augustine, they could start to be a legit team soon, but contenders, not for a while.
San Jose Sharks
This past season could be seen as the best-case scenario for GM Mike Grier’s Sharks. They played meaningful games in April, and they somehow still landed the second overall pick in a good draft class.
Having Macklin Celebrini changes the whole game. This past year has added expectations to the Sharks and their attempt to make the playoffs next season, in what might be another weak Pacific Division.
The core of Celebrini, Will Smith, William Eklund, and Michael Misa is one of the better young forward groups in the NHL for the coming years. The Sharks could be a true contending team by the 2027-2028 season.
Who knows if current head coach Ryan Warsofsky will be the team’s head coach during their contending window? This team is almost ready, but it shouldn’t be surprising if they have a similar season to the one the Montreal Canadiens just had.
Chicago Blackhawks
Connor Bedard is heading into this summer as an RFA, so GM Kyle Davidson has to get the chequebook out and give it to Bedard. If they complicate this contract, it could lead to a really awkward situation with the team’s franchise player.
Before the Blackhawks can become serious contenders, they need to find a No. 1 defenseman or at least have current young blueliners step up. There’s a path where Alex Vlasic turns himself into a Jaccob Slavin-type player, but there still has to be an emphasis in that department.
They have the fourth overall pick, but have the option of moving it. With Anton Frondell looking like a legit player already, a win-now move could be risky, but the league is getting younger and faster every day that passes, so winning while you still have key players on entry-level deals is so important. Expect to see them step into a contender in the 2028-2029 season.
Columbus Blue Jackets
Based on the past two years, Columbus may not be that far away.
Adam Fantilli has continued to develop as a two-way center who can play in all situations. He added more physicality in his game this year, going from 113 hits last season to 139 this past season. Also, he left room for improvement in terms of faceoffs, winning 41.2 percent of his draws in 2024-25. In 2025-26, he improved to 49.8 percent.
Not to mention Zach Werenski just won the Norris Trophy and has had back-to-back seasons at over a point per game. Jackson Smith, a 19-year-old at Penn State, and Denton Mateychuk, who just had a 13-goal season in the NHL, will be great defensemen for Columbus in the coming years.
Jet Greaves is an RFA with arbitration rights this summer and is looking like one of the best young goalies out there right now. In just his first full NHL season, he played 55 games, which is no joke.
The Blue Jackets could be one big trade or signing away from truly being in contention. But if they can’t see success while Werenski is at the top of his powers, it could be a very harsh rebuild. GM Don Waddell could be a busy man this summer.
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