Insider reveals what it would take for Penguins to re-sign Sidney Crosby

When the Pittsburgh Penguins decided to part ways with forward Jake Guentzel last Friday, it was not only emblematic of a retooling period for the storied organization but could be a sign of things to come. Still the oldest team in the National Hockey League by more than a year on average, the current iteration of this Penguins team is certainly going quietly into the night.

With the main core of Sidney Crosby, Evgeni Malkin, Kris Letang and Erik Karlsson on the wrong side of 30, Pittsburgh is quickly encroaching upon a future where Bryan Rust, Rickard Rakell and Marcus Pettersson lead the team. Not to be taken as a knock on either of those three players, but it will certainly not be good enough for the Penguins to be a competitive team in the Eastern Conference unless some major changes take place.

As difficult as it is to imagine Crosby wearing the sweater of any other team, it is becoming a disappointing end to one of the greatest careers in the history of the game. Last season, Pittsburgh failed to make the playoffs for the first time in Crosby’s career since his rookie season, and are headed for the same outcome again this year.

Having one year remaining on his 12-year, $104.4M contract after this season, Crosby will have the option to leave the only team he has ever known in an attempt to finish his career on a high note. However, being one of the most humble athletes in the game today, there is little to no insight into which way Crosby is leaning.

In this week’s edition of 32 Thoughts, Elliotte Friedman shows a lot of empathy with Crosby’s frustration with the Penguins organization but believes the organization should do everything in its power to retain their franchise player. Friedman believes that if Pittsburgh were to offer Crosby a three-year, $30M contract, that should be enough to get him to remain with the Penguins.

However, to push back, Friedman’s ideas appear to be an oversimplification of the factors that have driven Crosby in his career. Even when he signed his mega-contract with Pittsburgh back in 2012, paying Crosby an AAV of $8.7M was a bargain contract for the Penguins.

Owning three Stanley Cup championship rings, two Conn Smythe Trophy victories and three Olympic Gold Medals, it is more than clear what has driven Crosby throughout his career. Being one of the most competitive athletes in sports history, Crosby is first and foremost concerned about winning, which is something Pittsburgh is not built to do over the next few years.

Of the top-10 highest point scorers in NHL history; Steve Yzerman, Mario Lemieux and Joe Sakic are the only three to have stayed with the same team throughout their careers, with the others not having the privilege of spending their entire career in one spot. Given that it is not irregular to see a generational player make a move like this, it would be inappropriate to think it would impact Crosby’s legacy in any way.

Nevertheless, if Pittsburgh pulls off some crafty moves this upcoming offseason, there is a legitimate chance they could turn things around. However, it is becoming increasingly likely that this organization is headed for a lengthy rebuild, which is something Crosby may not want to be a part of to finish off his incredible career.