Four Questions Penguins Face While Trying To Maximize Sidney Crosby Era

The Pittsburgh Penguins are approaching a pivotal point in the history of the franchise.

Sidney Crosby, one of the best players in both Penguins and NHL history, entered the offseason with one year remaining on his contract. There’s been nothing to suggest Crosby will finish his career anywhere other than Pittsburgh, but there still is plenty of uncertainty when it comes to the future Hall of Fame center and the franchise he’s represented since 2005.

With that in mind, here are four questions the Penguins face ahead of a crucial 2024-25 season.

1. Will postseason hiatus be halted?
Pittsburgh turned into a Stanley Cup playoff fixture once Crosby joined the organization. The franchise ripped off 16 consecutive postseason appearances after the center’s rookie season in 2005-06, winning three Cups over that span. But the streak came to a halt in the 2022-23 campaign and the Pens failed to bounce back last season. With Crosby in the twilight years of his legendary career, Pittsburgh should be as motivated as ever to give the future Hall of Famer another shot to add to his incredible résumé.

2. Buyers or sellers?
The Penguins were close to clinching a playoff berth last season, finishing only three points out of the second Eastern Conference wild-card spot. But one had to wonder if that slot would have been occupied by Pittsburgh had it hung onto homegrown talent Jake Guentzel, who was shipped to the Carolina Hurricanes before the trade deadline. Crosby didn’t seem thrilled about the move, and it’s easy to understand why. The Pens don’t need wholesale changes to become a playoff team this season, but a prudent midseason transaction could help with the goal of giving Crosby another crack at the Cup.

3. Can Crosby keep pace?
This admittedly feels like a foolish question to float out there. It’s almost like asking if Tom Brady still could perform at a high level ahead of any of his seasons after age 35. But in a sport as grueling and unforgiving as hockey, it’s fair to wonder if Crosby, who turns 37 next month, still can play at an above-average level. There shouldn’t be much worry for the Penguins and their fans here, though, as he’s coming off back-to-back 82-game slates in which he logged 93 points or more.

4. How will offseason additions pan out?
Pittsburgh didn’t approach the offseason quietly after missing the playoffs for a second straight season. The Penguins didn’t make any blockbuster signings that yielded headlines, but they brought in a few proven veterans who could help turn things around. Kevin Hayes, Matt Grzelcyk and Anthony Beauvillier have all been around the block, and Blake Lizotte could prove to be a low-risk, high-reward acquisition. Did those moves make Pittsburgh a Cup favorite? No. But they should make the club more relevant in the postseason conversation.