At a wrestling group I frequent, an interesting question popped up: "I know people often talk about wrestlers wanting to go to WWE before they retire just to finish out their career. And every time I see this it seem to be said in a way that somehow it’s less of a hassle than the indies and an easier ride for the end of their careers. And while the more consistent work probably makes that true payment wise, that schedule barely seems like a fun end of career slow down. I’m not even sure I’m phrasing this properly but I guess do folks think wrestlers who are nearing retirement head to WWE just to get a (potentially) bigger cash in? To check off some bucket list items before they retire? To have less question marks in their last few years? It just seems like such a grueling schedule to want to do when you’re more or less no longer in the best shape of your life, yknow? So what do you think the motivating factor is? And is it an actual trend or is it just perceived to be that way because a couple guys have transitioned to WWE later in their careers?"
Wrestlers have historically not made good decisions with their money, but I'd like to think that a lot of them have taken the lesson of their peers to heart and are thinking long term. Specifically, what will be they doing when they can't wrestle any more. Here are some pros of ending your career with at least one run in the WWE:
Older guys can still get one run with major money. Money in WWE might not be ways better as in the indies (see Young Bucks) but there's something to be said for the other opportunities: convention appearances, indie boost upon release, etc. Plus, if they get a Legends contract even for working a short stint or last run, with access to their intellectual property and merch, that would be so worth it (see Sting and Bret).
Alternate careers. Some old guys want to get back and see if they can join for a possible future lighter career change. The WWE does provide opportunities for on the job training (see Road Dogg). I don't think Chris Hero would ever be featured in the main roster right now. But doing the job in NXT seems to be his way in for an agent or trainer job in the future.