Seven superstars who broke through to win the Stanley Cup after long droughts

Matt Larkin
Matt Larkin(MLarkinHockey)
Detroit Red Wings captain Steve Yzerman

They call it the hardest trophy to win in sports for a reason. To capture the Stanley Cup even once, it means winning 16 games in the postseason, surviving injuries, overtimes and rowdy road environments. It means getting saves at the right times, the right bounces, the right everything.

As a result, plenty of legendary players have gone their entire careers without lifting the Cup, including Marcel Dionne, Jarome Iginla and Joe Thornton.

If Connor McDavid can’t get there with the Edmonton Oilers this year, he’ll be nine seasons into his career without hoisting the chalice. David Pastrnak will be 10 seasons deep should the Boston Bruins bow out. The Toronto Maple Leafs’ Auston Matthews just completed an eighth season without anything close to a championship.

But if the superstars wonder when they’ll ever break through and win one, they can take solace in the fact we’ve seen plenty of iconic players take a long time, some even carrying around unofficial choker labels, before finally earning rings.

Here’s a look at some prominent stars who took many seasons to win it all. The list only includes players who won it with the teams who drafted them. The idea here is to see which fan bases were rewarded for sticking it out long-term with their team’s foundational players. Also, I’ve stuck to true “franchise players,” the guys who were tasked with being the marquee performer on their teams. That’s why I omitted Alex Pietrangelo (11 years).

Mario Lemieux: 7th season

It took Mario the Magnificent five seasons just to make the playoffs at all. It’s not that seven years was an eternity to wait; it just that, relative to his one-in-a-lifetime talent, it was surprising that it took the Penguins that many seasons to go all the way. On a stacked team that included a rookie Jaromir Jagr and additional future Hall of Famers galore in Paul Coffey, Ron Francis, Larry Murphy, Joe Mullen, Mark Recchi, Tom Barrasso and even a greybearded Bryan Trottier, the Pens broke through for their first championship. Lemieux compiled an astonishing 44 points in 23 games en route to the Conn Smythe Trophy.

Joe Sakic: 8th season

The Nordiques were very bad for a very long time. After nabbing Sakic 15th overall in the 1987 draft, they landed the No. 1 pick in 1989 (Mats Sundin), 1990 (Owen Nolan) and 1991 (Eric Lindros, traded to Philadelphia a year later). Armed to the teeth with young talent, they busted out with a dominant team by 1992-93. But they stand as an example of a team that was willing to break up some of its young core to reach its ultimate goal. While Lindros was used to bring in a massive return including Peter Forsberg, GM Pierre Lacroix, who arrived in 1994, also sacrificed Sundin and Nolan en route to building his juggernaut. The Nordiques relocated to Colorado by 1995-96 and won the Cup in their first season there, led by an all-time playoff performance by Sakic, including 18 goals in 22 games.

Nathan MacKinnon: 9th season

Remember when Nate Dogg was a disappointment? Four seasons into his career. The 2023 No. 1 overall pick hadn’t topped his rookie highs of 24 goals and 63 points, and he’d competed in the playoffs once. By his fifth season, he busted out as an all-world talent, and he’s never looked back. He and the stacked Avalanche core, including Mikko Rantanen, Gabriel Landeskog and Cale Makar, were playoff disappointments for a while, never escaping Round 2 until 2021-22, MacKinnon’s ninth season. That was when Colorado’s collection of elite stars peaked at just the right time, augmented by some shrewd trade deadline additions in Artturi Lehkonen and Josh Manson.

Mike Modano: 10th season

Here’s another star who survived a franchise relocation before lifting the chalice. Modano made it to the Stanley Cup Final in 1990-91 on a stunning underdog Minnesota North Stars team that had 68 (!!!) points in the regular season, but his North Stars turned Dallas Stars were non-threats for most of the decade until Ken Hitchcock took over as coach beginning in 1995-96. They morphed into a powerhouse the following year. They built around drafted talents in Modano, Derian Hatcher and Jere Lehtinen but also brought in Hall of Fame veterans to help get them over the top in Ed Belfour, Joe Nieuwendyk and Brett Hull. They reached the summit in 1998-99 on Hull’s “foot in crease” overtime winner, arguably the most controversial goal in NHL history.

Steven Stamkos: 12th season

The Bolts had plenty of good runs in the Steven Stamkos/Victor Hedman years before embarking on their mini-dynasty beginning in 2019-20. They reached Game 7 of the Eastern Conference Final in 2010-11. They lost in the Stanley Cup Final in 2014-15. In fact, Tampa fell to the eventual Cup champion in 2011, 2015, 2016, and 2018. They even tied an NHL record at the time with 62 victories in 2018-19 before being shockingly swept by the Columbus Blue Jackets in Round 1 of the playoffs. There were enough instances of “almost” to warrant questions of whether Jon Cooper’s group would ever reach the promised land. They finally did so in the 2020 bubble. Stamkos only suited up for one game that postseason due to injury but did score, and he was a key contributor on the 2020-21 team that went back to back.

Alex Ovechkin: 13th season

If you’re in despair over your team’s inability to get over the hump, Ovechkin is the cap-era player to model your hopes on. By his 13th season, Ovechkin’s Capitals had never come close to a championship. They’d never even competed in the third round of the playoffs. But thanks to a Conn Smythe effort from Ovechkin, scintillating scoring from Evgeny Kuznetsov and a clutch turn in goal from Braden Holtby after he opened the playoffs on the bench, the Caps did it. No team in recent memory seemed to enjoy the aftermath more. The Caps’ post-Cup celebrations were epic.

Steve Yzerman: 14th season

Here it is. The granddaddy of late-career redemption stories. Yzerman, a three-time Stanley Cup champion and Olympic gold medallist, is so synonymous with clutch play now that it feels forgotten that the narrative in Detroit was once very different. If you don’t believe me, read this Oral History of the 1996-97 team in which I spoke to players and management. They choked in Round 1 of the 1993 and 1994 playoffs. They were shockingly swept by the New Jersey Devils in the 1994-95 Final. They were almost out of ideas, so they got desperate. They brought in Scotty Bowman as coach. They brought in Brendan Shanahan in a trade that included shipping out a Norris Trophy winner in Coffey and a promising young forward in Keith Primeau. And finally, they found the right chemistry to win it all, sweeping the Philadelphia Flyers in the 1997 Final. If you’re ever convinced your team and its franchise-pillar star will never win the big one, just think about Yzerman’s Red Wings.

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