Mid to late 20's? Are we looking at the same guys? Late teens/early 20's. Chelios was 22. 21 if you count I guess essentially walking onto the Habs late in the year and being the 2nd leading scorer in the playoffs. Pronger took a while to become Pronger.
I think the competitive environment as an older guy has something to do with it. None of the names mentioned missed the playoffs at 29/30/31 years of age. Some won Cups around then. Deep playoff runs. At the very least teams that had good regular seasons, and maybe disappointed come playoff time, but they were in the game, part of the conversation. Of course most were 30 in the non-cap era. Easier to trade if they wanted to go. Easier to bring talent in to help them. Pronger and Niedermayer were that age right around the lockout, then ended up on the same team to form a super-duo. With the cap.
It has to be tough for all 5 old heads on the team. And all the holdovers that were here the last couple years. Who wants to be 30+, a former top player, on a bottom of the league team? Relative to the sports world(because they're still making a crap ton of money as players), it's like, what the hell am I doing here? At least if you're Ovechkin, you may not have won the Cup earlier, but you were in the trenches every year. As fans, 1 Cup for 10 years of crap, most fans will take it. It'll die down around year 4, and then you start complaining again, but most will take the trade. I have no doubt that Doughty would not trade the Cups for anything later in his career, but as a player, you might rather be SJ than Carolina. As you're playing. When you're done, when you retire, if you were in Carolina you get to say I was in that one moment of glory. As you're active though, you get the moment, but then the next 500+ games are pointless in the context of competing against your peers? That doesn't sound fun.
The problem with the "Doughty: is he done or just bored?" experiment is that every year that goes by he just gets older. If he could only stay 28 until the Kings were done rebuilding. But he'll be what, 32, the next time the Kings probably have a chance to catch a spot? That's assuming things go well, and most of what they try works out. Maybe 33? 34?
Not that Doughty is the only one. I'm sure Patrick Kane has no interest in coming to work this year. All the guys left in SJ are up in the air as to what that team is anymore.