The Sidney Crosby story and why it ends in Pittsburgh

Barring something wild, I feel comfortable saying Crosby will retire a Penguin.

I usually try to stray from giving oxygen to internet rumor fires, but sometimes they become so big and so stupid, you just have to put something out there.

I’m going to put my flag in the ground now: Sidney Crosby is going to retire as a Pittsburgh Penguin.

Sure, I don’t have any inside sources or knowledge of what Crosby and his camp think, and hell, I could definitely be wrong. In a year and a half, he could be wearing another jersey, and everyone will point to this newsletter and call me an idiot.

What I do have is reading comprehension skills and two eyes that are connected to my brain.

The Penguins’ rebuild/retool began, unofficially, on March 8, 2024, when they sent Jake Guentzel to the Carolina Hurricanes. If there was any clearer sign they weren’t competing for a playoff berth, let alone a Stanley Cup, it was that move.

It was also the correct move. The Penguins had too many holes in their roster, not enough prospects to make up for it, and an aging cast of characters who were either on the tail end of their best years or fully out of them. Winning the Stanley Cup was about as realistic as me reaching the top shelf at Giant Eagle.

Since that move, Kyle Dubas has pretty much done exactly what a rebuilding GM does: sign short-term contracts to be traded, collect draft picks, and manage expectations. The Penguins are in a position they haven’t been since a sophomore at Harvard launched something called The Facebook.

What does that all have to do with Sidney Crosby?

Well, six months and eight days after trading Guentzel, he signed a two-year contract extension that kicks in at the beginning of this upcoming season.

If the captain had any consternation about the direction of the franchise, he surely would’ve played out this past season and either walked to free agency or asked to be dealt at the 2025 NHL trade deadline.

Instead, he re-upped with the only franchise he’s ever known as a professional.

While I totally understand in the attention economy that is the current media landscape, talking about the idea of one of the greatest players of all-time playing for another team can generate downloads, clicks, and shares, that’s really all it is.

It’s speculation built out of fantasy.

Seriously, if you want to numb your mind as a Penguins fan (or get irrationally angry), I’ve got plenty for you to check out.

Those are just two examples from shows that I enjoy. There is no shortage of discussion about this on social media, blogs, you name it, they all cite…well, the fact that the Penguins aren’t good anymore.

That’s their entire foundation. The Penguins are no longer a contender, so he must go.

Instead of making up a reality where Crosby’s time in Pittsburgh was different, I’ll just use one of his counterparts: Alex Ovechkin. Ovi’s time with the Capitals has been tremendous. They won the franchise’s first and only Stanley Cup in 2018. They watched him break a record once believed to be unbreakable, and they’ve had some remarkable regular-season success.

They have also advanced past the second round exactly once. That was 2018 when they won the Stanley Cup.

Maybe I’m not remembering it, but I don’t recall a fever pitch of “Alex Ovechkin should leave the Capitals because they are wasting him” stories and podcast industries. I’m sure there was. Any time a team with a generational talent doesn’t win, the calls for the talent to go elsewhere and win go up.

On the other side of it, let’s remember what Crosby and the Penguins have done since he entered the league.

They’ve won the Stanley Cup three times, including the first back-to-back championships in the NHL’s salary cap era. They’ve been to the Stanley Cup Final four times. They reached the Eastern Conference Final five times. They went to the Stanley Cup Playoffs a remarkable 16 straight years.

Hockey and the NHL have not been deprived of Sidney Crosby on the biggest stage. This isn’t even factoring in the amount of success he’s had at the international level to go along with his NHL successes.

If the Penguins had been some floundering, middle-of-the-road to bottom-of-the-barrel franchise in the 20 years Crosby’s been with the club, I could understand wanting to see him go elsewhere and try to win. Hell, we’re seeing that right now in this very city with Paul Skenes. Do you really think the Pittsburgh Pirates will suddenly become a championship-caliber team while he’s on a rookie contract? If you answered yes, I’ve got ocean-front property to sell you in Iowa.

The Penguins and Sidney Crosby have lived up to their end of the bargain. As a player and as a franchise, the Penguins were one of, if not the most, successful teams since the 2005 lockout. The Penguins did not waste him or his generational gifts. They maximized them.

I’ll end with this, and it’s a question the great Josh Yohe of The Athletic said to us on Locked On Penguins: What would be a better story: Sidney Crosby gets traded to a contending team like Colorado, or hangs around for this rebuild and just as it starts to come back around he goes on one last playoff run with the next generation?

I know my answer, and if you’re reading this, I bet I know yours, too.