Well firstly Flair had 21 World Title Reigns technically, not sure whether my source is correct though
8 WCW World Title Reigns, 6 NWA World Heavyweight Reigns, 2 WWF World Heavyweight Reigns were the official ones
anyway going with these stats technically Flair had 16 NWA/WCW/WWF world Title reigns, Triple H currently sits on 8 WWF/E World Titles, 5 (WCW) World Championships
very similar
But given technically Flair has 21 Trips is nowhere near, and personally i don't think he would want to out of respect. pass his official record, maybe. He will tie it at the least.
Or since Flair is now riding with TNA who's to say Vince doesn't push for the record to be broken
Dopesn't matter either way, it's just a title and stats don't mean shit really anymore since titles are thrown around like candy