The Tampa Bay Lightning let their captain and best player walk away in free agency. Will the Pittsburgh Penguins do the same with Sidney Crosby?

Sidney Crosby, Evgeni Malkin, and Kris Letang have skated together with the Pittsburgh Penguins since 2006. 

The trio's longevity rivals that of Derek Jeter, Marino Rivera, and Jorge Posada, who donned a New York Yankees jersey together for 17 seasons and won five World Series titles. 

The Penguins stars won Stanley Cup titles in 2009, 2016, and 2017. When they retire, Crosby and Malkin will be the first-ballot Hall of Famers, while Letang has a chance to get in at some point but is locked to make the team's Ring of Honor.

Heading into the 2024-25 season, Crosby will be 37, Malkin will be 38, and Letang will be 37. 

Considering the Penguins haven't played a playoff game since May 15, 2022, some say the club's contention window is closed.

After a 16-year playoff run came to a halt in 2022-23, Pittsburgh has switched general managers and made some roster adjustments. 

However, when the final buzzer sounded in April 2024, there was no extra hockey for the second consecutive spring.

Discussing the Future of Crosby, Malkin, and Letang

Crosby has one year left until free agency. Malkin's deal expires at the end of 2025-26, followed by Letang in 2027-28.

As a franchise icon on the same level as Mario Lemieux, there will be much talk about Crosby's future in the coming 11 months. 

Until he signs a new deal or gets traded, it will be a wild season speculating on his future.

Yet, we don't need to look further than what happened in Tampa Bay on Monday. 

The greatest player in franchise history, Steven Stamkos, was allowed to walk away in free agency after 16 years, 1,137 points, and two Stanley Cup championships.

It was a horrible day to be a Lightning fan, but at the same time, a decision had to be made to keep their contending window open, which they did by signing former Penguins star Jake Guentzel.

Interestingly, Stamkos is not the only future Hall of Famer released at the end of his career to pursue more hockey in a different location. 

For example, the New York Rangers let Henrik Lundqvist go, the Ottawa Senators let captain Daniel Alfredsson walk, and the Dallas Stars allowed Mike Modano to play elsewhere.

For those sentimental fans, even Ray Bourque, the highest-scoring defenseman in NHL history, had to leave the Boston Bruins to win a Stanley Cup, which he did with the Colorado Avalanche.

So, while no one ever wants to see their heroes leave, there is a trend in the NHL for it. This means general manager Kyle Dubas is in quite a situation.

Does he continue to try to maintain a contender built around a trio of stars, or does he let Crosby ($8.7 million AAV) chase another Stanley Cup with another team? Will he explore all options to move Malkin ($6.1 million) or Letang ($6.1 million)?

If any or all three players left Pittsburgh, that's a potential savings of $20.9 million in cap space.  

Before anyone gets upset, this isn't about cap space or even legacies. Jaromir Jagr left the Penguins in 2001 and is still considered a hero in town over two decades later.

If Crosby, Malkin, and Letang left, the team's fanbase would be cut in half, but as the saying goes, time heals all wounds.

Despite what the fans, the players, or coaches want, the future of these three players falls on one man: Dubas. He needs to think about the next season and the one after that.

Ultimately, Crosby has earned the right to retire in a Penguins uniform or pursue more personal success elsewhere. 

The same can be said about Malkin and Letang, but both have years left on their deals, making a move a little more complicated.

No matter what happens between today and July 1, 2025, Penguins fans must understand that superstar players always move. 

The days of players spending their entire career with one franchise, like Lemieux, Steve Yzerman, and Jean Believeau, are gone. 

The NHL is more of a business than a sport today, hence the work stoppages in the past three decades—money and opportunity trump loyalty almost every time. 

Although no one wants to talk or even think about it, franchise icons relocate. 

If that happens in Pittsburgh this summer or next, everything will be okay, and departed players will receive a standing ovation upon their return.

Everyone needs to remember if a player with Stamkos' statue can be moved, let alone be allowed to walk away, anything is truly possible in today's NHL.

This means there are no guarantees for Crosby, Malkin, or Letang.