Down Goes Brown: Five legends who waited longer than Alex Ovechkin to win a Stanley Cup

Sean McIndoe
By: Sean McIndoe
May 18, 2016

Alex Ovechkin and Steve Yzerman. (Getty Images) Author: The Hockey News


Down Goes Brown: Five legends who waited longer than Alex Ovechkin to win a Stanley Cup

Sean McIndoe
By: Sean McIndoe
May 18, 2016

Remembering five legendary players who took until at least their 12th season to finally get their hands on a Stanley Cup.

Alex Ovechkin has been under the spotlight for the past week, following the premature end to the Washington Capitals' dominant season at the hands of Sidney Crosby and the Pittsburgh Penguins. He's been criticized for a lack of production at key moments and an inability to lead the Capitals to a deep playoff run, and took further heat for his decision to head to Russia right away for the World Championship.

Not everyone agrees, with plenty of voices defending Ovechkin's track record. But the fact remains: 11 years into his NHL career, Ovechkin has racked up record-breaking numbers and plenty of individual awards, but no Stanley Cup.

So it may be worth remembering that still leaves him in pretty good company. Plenty of legendary NHLers never won it all, with names like Marcel Dionne, Gilbert Perrault and Darryl Sittler failing to earn a ring. But there have also been plenty of superstars who did get their Cup, but had to wait for it. And in some cases, they waited a lot longer than Ovechkin has.

So today, let's offer up some hope to Ovechkin (not to mention guys like Henrik Lundqvist, Roberto Luongo, Joe Thornton and the Sedins) by remembering five legendary players who took until at least their 12th season to finally get their hands on a Stanley Cup.

Ray Bourque

The long wait: Probably the first name that came to your mind when you saw this list, Bourque's drought lasted a stunning 21 years, during which he captured the Norris Trophy five times and was a first-team all-star 12 times. Despite being the generation's best defenseman, he debuted in the 1970s and made it to the turn of the century without earning a ring.

Worst near-miss: The Bruins made the final twice during Bourque's career, in 1988 and 1990. But both times, they ran into the Edmonton Oilers, and they only managed to win one game between the two series. (They also managed to become the only team in final history to be swept in five games, thanks to a Boston Garden power failure that forced the suspension of a game in 1988.)

How it finally ended: The good news for Ovechkin is that Bourque finally did get his Cup. The bad news for Caps fans is that it took a trade for it to happen. The Bruins dealt Bourque (at his request), sending him to Colorado at the trade deadline in 2000. The Avs didn't win it all that year, but Bourque returned for one final run, and finally got his Cup in 2001, becoming the most iconic OGWAC story of all-time and leading to this moment that still makes you cry a little bit.

Dominik Hasek

The long wait: Hasek's career was all about waiting. He didn't make the NHL until he was 25, and didn't become a fulltime starter until he was 28. But from there he quickly established himself as the league's very best, winning the Vezina six times in eight years. But with the Sabres declining and a big option year payday looming, Hasek's time in Buffalo came to an end in 2001 without a title.

Worst near-miss: Well, there was this

How it finally ended: It's easy to forget now, but the trade that sent Hasek to Detroit was an odd one at the time. The Red Wings already had Chris Osgood, who'd won two Cups for them. But Hasek represented a clear upgrade, so they made the move, and it paid off. They won the Cup, Hasek got his ring, and then retired. It was a storybook ending.

(Then he came back a year later, shivving Curtis Joseph and eventually teaming with a returning Osgood to win a second Cup in 2008. Look, it was Dominik Hasek, the storybook was always going to be a weird one.)

Johnny Bucyk

The long wait: The future Hall of Famer broke into the NHL with the Red Wings in 1955. After two years in Detroit, he was dealt to Boston for Terry Sawchuk in what turned out to be one of the bigger trades in NHL history. Much like Bourque, he found that winning a Cup in Boston was easier said than done, even in the Original Six era.

Worst near-miss: Bucyk and the Bruins lost in the final in his first year there, in 1958, and again over a decade later in 1969. In between, they endured an eight-year stretch where they missed the playoffs every season.

How it finally ended: In his 15th season and just two days before his 35th birthday, Bucyk finally got his first Cup in 1970 when Bobby Orr scored his famous overtime winner.

Bucyk won a second Cup two years later, and played in the NHL until the age of 42.

Teemu Selanne

The long wait: Selanne was drafted in 1988, debuted in 1992, played for four teams and was an all-star ten times by the time the 2007 playoffs arrived. But at 36 years old, he'd never been to a Cup final. And much like Ovechkin, he made it through the first dozen years of his career without even making it out of the second round.

Worst near-miss: Selanne finally got a taste of the conference final in 2006 with the Ducks before losing to the upstart Oilers. But his toughest miss probably came in 2003-04, when Selanne and Paul Kariya took massive paycuts to join a star-studded Avalanche team that looked like it could streamroll to a championship. Instead, he had the least productive season of his career and the Avs went out in Round 2. To make matters even worse, they were knocked out by the Sharks, the team Selanne had left to come to Colorado.

How it finally ended: Selanne and the Ducks finally broke through in 2007, beating the Senators in five to capture the Cup for the first time. Everyone felt happy that Selanne could ride off into the sunset with a title. Then he played for seven more years.

Steve Yzerman

The long wait: Let's take pity on Washington fans by ending with a guy who won his championship without ever playing a game for another franchise. Despite being recognized as one of the best players of his generation, Yzerman was still without a Cup 13 years into his career. That was despite putting up gaudy offensive numbers and leading the Wings to all sorts of regular season success, both of which may sound familiar to Caps fans.

In fact, as bizarre as it sounds now, there was a time when it wasn't uncommon to hear hockey fans talk about Yzerman the same way so many talk about Ovechkin today. He was a regular season player, a numbers guy who didn't know how to come through when it counted. There was even talk of trading him, including a rumored deal that would send him to Ottawa for Alexei Yashin.

Think about that: There were people who thought that if Detroit wanted to win it all, they had to replace Steve Yzerman with Alexei Yashin – and their ranks included plenty of Red Wings fans. Keep that in mind the next time somebody tries to tell you that the Capitals need to move on from Ovechkin.

Worst near-miss: The Red Wings were swept in the 1995 Cup final, but 1996 was probably more painful. That was the year the Wings won an NHL record 62 games, then lost to the Avs in the conference final to launch the legendary rivalry between the two teams.

How it finally ended: The Red Wings didn't panic after that 1996 disappointment. They stayed the course, added a few more pieces, and passed on Yashin-for-Yzerman. Then they went out and won back-to-back Cups, followed by a third in 2002. Yzerman retired in 2006 and is now viewed as one of the greatest winners in NHL history. If you're an Ovechkin fan looking for the best-case scenario, it looks a lot like this.

Sean McIndoe has been writing about the NHL since 2008, most recently for ESPN and Grantland. He spends most of his time making jokes on twitter, where you may know him as @downgoesbrown. He appears weekly on

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Down Goes Brown: Five legends who waited longer than Alex Ovechkin to win a Stanley Cup