The Pittsburgh Penguins sit at a crossroads. While Sidney Crosby and Evgeni Malkin still anchor the roster, GM Kyle Dubas hasn’t made any big offseason moves. The front office appears to be leaning toward a youth-focused strategy that might not align with Crosby’s closing championship window. The writing may already be on the wall.
What Major Move Could Pittsburgh Make To Keep Veteran Sidney Crosby Happy?
Several core veterans are being shopped around the league. Erik Karlsson, Bryan Rust, and Rickard Rakell have all surfaced in trade discussions. There’s growing belief that none of them will still be wearing Penguins jerseys by the time the 2026 trade deadline arrives.
One source close to the team revealed the organization’s true intentions: “I expect the Penguins to do everything in their power to get into the top-3 of the 2026 Draft.”
This creates a timing problem. With Malkin entering what could be his final season under his current contract and Crosby’s own future uncertain, the team faces pressure from multiple directions. The crucial decision looms: pull the plug early on this core or wait and make a splash midseason to outmaneuver lottery-bound teams like San Jose or Chicago.
How Long Will Sidney Crosby Wait For Another Championship?
Crosby has never suited up for another franchise. He’s delivered Pittsburgh championships, remained loyal through rebuilding years, and continued producing at an elite level. But even his patience has limits.
Speaking on The FAN Pregame, analyst Jason Bukala said, “Pittsburgh is not going to be very good for a long time. He’s going to age out of that roster and go win somewhere else.”
Don’t miss Hour 2⃣ of The FAN Pregame with @jccuthbert & @jesserubinoff
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At 37, Crosby continues putting up elite numbers with 90-plus points in each of the past three seasons. However, Pittsburgh finds itself trapped in no man’s land. They aren’t terrible enough to secure a top draft pick, yet they’re nowhere close to being Stanley Cup contenders.
As veteran teammates appear headed for the exit, Crosby faces the prospect of being surrounded by unfamiliar faces and diminishing playoff hopes. The question becomes whether he’s willing to waste his remaining prime years on a rebuild.
Despite signing a two-year extension recently, reports suggest Crosby might be quietly exploring his options behind the scenes. Frank Seravalli claimed the superstar may already have identified potential landing spots.
Frank Seravalli: Re Sidney Crosby: I think there’s been some teams, or a short list, Montreal, LA Kings, Avalanche, those are the teams have been talked about, but he hasn’t shown any interest…in moving – Bleacher Report (Jul 15)
— NHL Rumour Report (@NHLRumourReport) July 17, 2025
NHL front offices are monitoring the situation closely. The prevailing sentiment around the league is that it’s no longer a question of if Crosby would consider leaving Pittsburgh, but when and under what circumstances.
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The captain maintains complete control over his destiny. He’s earned that right through years of loyalty and excellence. But if the Penguins continue drifting without a clear direction, Crosby may decide to pursue one final Stanley Cup run elsewhere before hanging up his skates.
