Column: Comparing Crosby to late careers of other NHL greats

Oct. 19—The nickname "Sid the Kid" is just blatantly incorrect nowadays. He's 36.

Sidney Patrick Crosby just entered his 19th season in the National Hockey League, and while he is still not showing any signs of slowing down, the dude's pushing 40 and with that... he will be retiring sooner rather than later. But don't cry yet. It's not over until he says so.

Crosby is hardly the first superstar hockey player to play past 35. Countless other Hockey Hall of Famers have done it. But did any of them win anything relevant in the twilight years of their careers? Today, let's look at some of the greatest players in NHL history who managed to play deep into their late-30s to try and get a sense of what we can expect to see from Sid over the next few years.

Cup-less

I've grouped the players I want to talk about into a few different categories. The first is thankfully a category that Crosby has been out of since 2009, players who never won a single Stanley Cup.

It is saddening, but several legendary players like Joe Thornton, Patrick Marleau, Jarome Iginla, Mats Sundin and Eric Lindros despite multiple accolades, thousands of games played and several deep playoff runs, never got a Cup.

This typically led players like them to leave the team in which they have spent the bulk of their career with to go to a contender to try and win a Stanley Cup. Some even came to the Penguins.

With three Stanley Cup rings to his name, Crosby will thankfully not be bouncing from team to team desperately chasing his first opportunity at the ultimate prize.

One more taste

Instead, Crosby falls into the category of players who want another taste of Lord Stanley's Cup. However not all players in the past stayed loyal to their teams in this endeavor.

Some players won Stanley Cups with a specific organization, then moved on to other teams in the twilight years of their careers for a "better shot" at the Stanley Cup.

Wayne Gretzky and Mark Messier going to New York, Ron Francis signing in Toronto or Mike Modano playing with the Red Wings are all examples of this.

While technically speaking Crosby could request a trade and go to a team like the Lightning or Avalanche who might have "better shots" at the Stanley Cup nowadays, I think we all know he's going to stay in Pittsburgh until he retires.

One team man

So that leaves us with players who stayed with one team throughout the entirety of their career. These are the players I think are the best in terms of a comparison for Crosby.

They are: Steve Yzerman and Nicklas Lidstrom with the Red Wings, Joe Sakic with the Nordiques/Avalanche organization and Patrice Bergeron with the Bruins.

All of these players were drafted by a team, won Stanley Cup(s) with said organization and then retired with the same franchise. It's a tremendous and rare accomplishment that can only be said for a few athletes in sports history.

(Seriously as great as they are, guys like Gretzky, Michael Jordan, Tom Brady and Babe Ruth can't even say they have done this).

Comparing Crosby

Looking at the careers of some of these one-team wonders give us some encouraging results (at least if you are a Penguins fan like me). Steve Yzerman won his final Stanley Cup (2002) at the age of 36 and also won a Masteron Trophy for dedication to the game when he was over the age of 35. While a defenseman, Nicklas Lidstrom won four Norris Trophies (best defensemen) and a Stanley Cup at 37. Patrice Bergeron won two Selke Trophies for best defensive forward in the NHL and two Mark Messier Awards for leadership when he was over 35 years old.

Outside of continuing to climb up the NHL's all-time goals, assists, points and games played leaderboards, there are a few individual awards I think Crosby can still win in 35-plus club. I think a Messier, Masterton or Selke Awards are all in the realm of capability for Sid.

While all of these individual awards help bolster Crosby's legacy, another Stanley Cup would likely cement him as a top-five player all time.

Deja Vu?

The oldest player to win a Stanley Cup was Chris Chelios in 2008 with the Detroit Red Wings. He was 46. That same year, Lidstrom, captain of the Red Wings, raised the Stanley Cup at 38-years-old, making him the oldest captain to win it all as well.

Fittingly enough, at the other end of the ice that year was a 20-year old Crosby and the Pittsburgh Penguins who lost the 2008 Stanley Cup Final against the Red Wings. The next year, the same two teams met in the Stanley Cup Final and this time, Crosby and the Penguins won.

You can look back on this series as the passing of the guard from one generational team to another. The Red Wings won four Stanley Cups in 11 seasons and made the playoffs 25-straight times. The Penguins then went on to win three Stanley Cups in nine years make the playoffs in 16-straight seasons.

How cool would it be for this to happen again? Except for this time, Crosby and the Penguins are the team that is running out of gas. Erik Karlsson might have been the right addition for the Penguins to go to the Finals against Connor McDavid and the Oilers and for the cycle to repeat.

My biggest issue

I won't go into full critique mode here on the Penguins current roster, but I will address possibly the biggest thing I have failed to mention so far. That is that guys like Chelios, Lidstrom and Yzerman had fantastic teams around them when they won Stanley Cups in their late 30s. The 2002 Red Wings might just be the most stacked NHL roster of all time as nine players from that team are currently in the Hockey Hall of Fame. Yzerman was sixth in scoring for them that season. And while the 2008 Red Wings still utilized Lidstrom a lot, they had stars like Pavel Datsyuk and Henrik Zetterberg to help take the weight off.

My point here is that, as great as he is, I don't know if Crosby can lead the team to another Stanley Cup. Now, could he be a key cog in another championship like Lidstrom or Yzerman were? Absolutely.

Don't get me wrong I don't want Crosby to stop playing like he does, instead I want to see someone, maybe Jake Guentzel, maybe Erik Karlsson or someone new establish themselves as the Penguins future and help Crosby in whatever way they can for one last Stanley Cup.

Owen Krepps can be reached at 814-724-6370 or at owenk@meadvilletribune.com.