Sidney Crosby is bumming me out these days.
Not because he’s playing poorly. Quite the opposite — even at 37, he’s still scoring and playing a strong two-way game. No, the sad part is that it’s not anywhere near enough for the Pittsburgh Penguins. With a sub-.500 record in a surprisingly tough division, their season already looks like a lost cause.
If so, it will be the third straight year that Crosby misses the playoffs. And with two more years left on his extension, and little in the way of optimism that the aging Penguins can get any better, getting to five straight doesn’t seem unrealistic. Assuming he doesn’t push for a trade, it’s legitimately possible we’ve already seen the last of Sidney Crosby in NHL games that actually matter.
Maybe things will turn around in Pittsburgh. But if not, Crosby could at least take some solace in knowing he won’t be the only legend to end his career with little or no playoff action. It happens more than you might think, especially regarding players who are still performing at a high level. You’d think the hockey gods would ensure every star gets the send-off they deserve, but for every Ray Bourque or Lanny McDonald or Mark Recchi who goes out on top, or even an Adam Oates who at least comes close, some stars never get that chance.
Let’s remember a few of those guys, if only to make Sid feel better. OK, fine, to make me feel better about where Crosby might be headed.
Mark Messier
The consensus pick as the greatest leader in NHL history won two MVPs, a Conn Smythe Trophy and six Stanley Cups, including the one that snapped the Rangers’ 54-year drought. That came in 1994 when he was 33 and already had one of the greatest resumes in modern league history.
Then he kept going.
At first, that was fine. He helped lead the Rangers to the playoffs for three more seasons and even finished as Hart Trophy runner-up in 1996. But in 1997 he left for Vancouver. While that was a great signing for the Canucks, they missed the postseason in all three of Messier’s years there. He returned to the Rangers in 2000, just in time to be part of four more playoff-less seasons.
Add it all up, and that’s seven straight years across two different teams that the sport’s greatest leader couldn’t lead his team to the postseason. He finally retired at the end of the 2005 lockout at 44, and the Rangers immediately made the playoffs without him.
Sadness index: At the time, it was pretty high. But since we all apparently had a big meeting at some point and agreed to never mention this again, I guess I have to nudge it down to an 8/10.
Mark Messier skates with the Rangers in a game against the Maple Leafs in October 2002. (Dave Sandford / Getty Images / NHLI)
Pavel Bure
By 1994, Pavel Bure was a first-team All-Star, had just posted his second straight 60-goal season and had helped lead the Canucks to an inspiring playoff run that fell just one game short of the franchise’s first championship, over which he’d scored a postseason-leading 16 goals. Oh, and he had just turned 23. The sky was the limit. We thought.
One season later, the Canucks were swept in the second round. We couldn’t have guessed it at the time, but that opening-round victory featured the last playoff game Bure ever won.
Vancouver made the playoffs again in 1996, going out in the first round, but Bure was hurt and couldn’t play. The Canucks missed the playoffs in 1997 and 1998, after which Bure was traded to the Panthers in the offseason. He spent three full seasons in Florida where despite leading the league in goals twice, he only saw playoff action once — a four-game sweep to the Devils in 2000.
Like every star on the wrong side of his 30s in that era, Bure was eventually traded to the Rangers, where he was part of those late-era Messier teams that missed the playoffs each year. By the time injuries had cut his career short, he’d played his final eight seasons for three teams without winning a single playoff game.
Sadness index: 7/10. At least he made the playoffs, albeit briefly. But like a few guys on our list, he gets bonus marks because he never did win a Cup.
Eric Lindros
Nobody in a generation had come into the league with more hype than Eric Lindros, and for eight seasons he largely lived up to it. It took him two years to get the rebuilding Flyers into the playoffs, but between 1995 and 1997 he led the team to six wins in nine rounds, culminating in a trip to the 1997 Final that saw Lindros post a league-leading 26 postseason points.
It turned out to be the peak of a career that was about to be decimated by injuries. Lindros and the Flyers made a first-round exit in 1998, and he missed the 1999 postseason due to injury. Another injury set the stage for a dramatic comeback in the 2000 conference finals, which ended in one of the most dramatic moments of the era.
That was the last game Lindros played for the Flyers. He sat out a year to recover and force a trade, then spent three years with that pre-lockout Rangers team that keeps showing up here. After the lockout it was on to a season with the messy Maple Leafs, who missed the playoffs, and then a final season in Dallas. He did make the playoffs that year, returning to the postseason for the first time since the Scott Stevens hit. But the Stars lost in the first round, and Lindros was only healthy enough to contribute three games without points.
The career totals from the moment Lindros ran into Stevens’ shoulder: Seven years, five seasons, three playoff games, zero points.
Sadness index: 9/10. Still one of hockey’s all-time “What if he’d stayed healthy?” stories.
Alex Delvecchio
Alex Delvecchio’s career was one of the longest — 24 seasons in all — and most productive in NHL history. It was also spent entirely with the Red Wings, which will give you a sense of where this story is going.
Playoff success came early. Delvecchio’s first full season was in 1951-52, joining a Red Wings powerhouse that already featured legends like Gordie Howe, Ted Lindsay, Red Kelly and Terry Sawchuk. Not only did they win the Cup that year — they didn’t lose a single playoff game while doing it. They won in 1954 and 1955, too, meaning Delvecchio had three rings before he turned 23.
While that would be it for championships, Delvecchio and the Red Wings were playoff regulars throughout the rest of the Original Six era, including five trips to the Final. But expansion signaled the end of the Red Wings as contenders and the end of Delvecchio’s playoff success; they lost in the 1966 Final and then fell out of the playoff hunt.
The future Hall of Famer played for Detroit until early in the 1973-1974 season, at which point he retired and took over as head coach and (shortly after) general manager. He held both of those roles until 1977. But in those 11 years spent as player, coach and GM after the 1966 final, Delvecchio and the Wings only saw postseason action once — in 1970, when they were swept in the first round. They didn’t win a single playoff game in the last decade-plus of Delvecchio’s career with the team.
Sadness index: Sadness? More like darkness. As in the Darkness with Harkness, which is what that era of Red Wings hockey came to be known as in (dis)honor of early ’70s GM Ned Harkness. The Wings didn’t win another seven-game series until 1987.
Marcel Dionne climbs over the boards to join the Kings’ action in a 1980 game against the Islanders. (Bruce Bennett Studios / Getty Images)
Marcel Dionne
This might feel like piling on, given Marcel Dionne almost certainly has history’s highest ratio of regular-season-to-playoff success. He retired as the second most productive scorer the NHL had ever seen, and still ranks sixth, but somehow never even made it out of the second round.
So, sure, maybe you wouldn’t expect him to have much of a late-career playoff resume. And sure enough, he has just two appearances in his last six seasons, both first-round exits that lasted a combined nine games.
The frustrating piece here is that, unlike players like Crosby or Delvecchio, Dionne wasn’t loyal to just one struggling franchise. He orchestrated his way out of Detroit in the ’70s and headed to L.A. for a second chapter while still in his prime. And he finished his career with the Rangers — yes, them again — when they were at least a solid playoff team and not too far from legitimate Cup contenders.
So, what happened? After missing the postseason in his final year with the Kings, he was traded to the Rangers at the 1987 deadline. They made it but went out in Round 1, and then missed the playoffs a year later despite Dionne scoring nearly a point per game at age 36. And then, with the Rangers headed toward a playoff berth midway through the 1988-89 season, Dionne just … quit. Tired of ongoing squabbles with the Rangers front office, he retired midway through the season and started a dry-cleaning company.
Sadness index: 8/10. Um, maybe nobody tell Crosby about that whole “retiring to become a dry cleaner” option.
There’s still one name to go, but first …
Dishonorable mentions
While it’s not quite at the same level as some of these other stories, Wayne Gretzky missed the playoffs in each of his last two seasons, as did Jarome Iginla and Paul Kariya. Pat LaFontaine, Roberto Luongo and Jonathan Toews missed in three, while Ryan Getzlaf and Theo Fleury missed the playoffs in each of their last four seasons. And Brian Leetch was yet another casualty of those pre-lockout Rangers; he only made the playoffs once in his final eight seasons.
OK, on to our final name.
Mario Lemieux
As if we weren’t bringing down Penguins fans enough.
Yes, we have to mention Mario, whose emotional comeback allowed his unparalleled career to overlap with Crosby’s for one partial season. That comeback came in December 2000, a midseason stunner that still ranks as one of the greatest nights I can remember. (The banner being lowered still gets things a little dusty around here.) Lemieux basically picked up where he’d left off, which is to say making everyone else in the league look silly. He led the Penguins to the playoffs where they won two rounds before bowing out in the conference finals.
Unfortunately, while Lemieux played parts of four more seasons, that 2001 run spelled the end of his playoff story. The Penguins missed the postseason in each of the last three years before the lockout, and then again in 2005-06. That season was Crosby’s debut and Lemieux played the final 26 games of his career. After two Stanley Cups, two Conn Smythes and a borderline ridiculous 1.60 points-per-game playoff resume, Lemieux didn’t get a postseason invite in any of his final four seasons.
Sadness index: 6.6/10. This was awful because we missed out on Mario’s playoff brilliance, but we were just glad to have him back at all. And Pittsburgh fans knew the team was in good hands with the passing of the torch to this Crosby kid, who’d lead them to 16 straight postseason appearances before … well, you know.
(Top photo of Sidney Crosby: Claus Andersen / Getty Images)
