For the sake of discussion, I will comment - I have NEVER, not ONCE been mad at Sidney Crosby since his draft day in 2005. That said, I can say that if he is at the point where is suggesting "hmm...I may not resign if we are not going to be competitive" then I have a significant problem with that because I believe that, more likely than not, it is HIS well-earned stubbornness and catering to that has played a bigger role than we want to admit for the mess we are in. Now, on one hand, there's just a general cyclical nature to team success. We all knew full well that when Sid and Geno got old, the team wouldn't be as competitive. In the pursuit of the cup when it made sense, they went for it. They mortgage the future constantly for pursuit of the cup and that's fine. It's hard to win the Cup and Sid has three with two conn smyths. It's hard to ask for much more. But at this point, there are some glaring issues that we can point to that are, at the root cause, Sid's fault.
Number one - the continued employment of Mike Sullivan. This offseason, a lot pointed to the premise that: 1. FSG likes Sullivan. 2. The core loves Sullivan and doesn't want to play for anyone else and 3. Sullivan may not have opted to leave because he's loyal to Sid and Geno. Coaching has been a MASSIVE issue for this team for 5+ years. To the point where other "fixes" are merely window dressing for a team rotting from the inside due to the unwillingness to move on to something different. If Sid has alluded to Sullivan being the only Penguin coach he's willing to play for, THAT is an issue and it's a Sidney Crosby issue.
Next, we have seen Sid be very selective with linemates to the point where line combos are put together that go against better judgment and better performance. To that end, we have seen the organization keep players on this roster that should have traded a while ago to recoup the assets needed to maintain performance. For example, Letang, Rust, and Guentzel. Now, we did trade Guentzel for an appropriate return but I don't think it was a secret that people were upset. They went out of their way to tell Rust that they love him though even though there was every incentive to ship him off as well. We should have done so if Detroit had been interested and we could have gotten a similar return to Guentzel (or slightly less). We could have replaced both Jake and Rust in free agency recently.
Those are issues that have festered and manifested themselves in significant ways, but we were happy to do so because that is what Sid wanted, and certainly, it's understandable that you give your franchise legend what he wants. If he's coming back now and saying, "Oh, wait, yeah, now it's a problem...but I'm also not going to support the moves necessary to make the changes,"...then that's a Sidney Crosby issue. That's a level of "unfairness" that is concerning to my viewpoint of Sid. That's a "no, don't turn the Titanic away from that iceberg. That would disrupt my life too much...oh...well now that the ship is sinking I wish to get on the lifeboat first" approach.
The organization set in place a plan to revamp as quickly as possible for the twilight years of Sid's career. To turn back now...especially after Geno and Letang resigned to be lifers...just sucks. Now this all said, it's not like I wouldn't be thrilled for Sid to join a playoff team and win another Cup. I would love nothing more but it sacrifices the "life long Penguin" aspect that I think would be important to his overall legacy. I don't think another Cup changes much. Finishing top 5 in points with a single team while ushering in a new era, that is a very Sidney Crosby-esque way to go out. To jump ship at the last minute...ouch.