To play upon my post earlier, my problem with Trips isn't with his declined in-ring skills or backroom politicing... after all he's not the first to possess either trait and won't be the last.
My problem stems from two related things. First is that, since dropping the DX-styled bad-boy character around 2000 or so, I have no idea what his character is supposed to be. Now, that isn't to say that all wrestlers need an identifiable character, but when you get as much TV face-time as Trips has had the last five years, you should have something you can point to (ex: During their primes: Hogan as super-patriot; Flair as playboy). This leads to my other problem: His interviews.
"I'm among the greatest wrestlers ever! Don't bother challenging me because I will beat you! Also, I like having the world title!"
Not really a whole lot to them, but somehow he manages to parlay that into weekly 15-minute interview segments that go absolutely nowhere.
Conclusion: Even if I can ignore the skills/politics issues, I'll remember Triple H as a guy who just happened to be there.