This is one of the easiest questions ever. HBK by the WIDEST margin EVER.
HBK has had countless classic matches with a variety of opponents, had revolutionary concept matches (HIAC and Ladder)that became big staples and draws for the E. NONE of that can be said about Triple H. Not to mention HBK is one of the best promos in the history of the biz.
I would like to say HHH is NO slouch, but there is NO validity in comparing him to HBK. HBK straight worked his way to his spot, HHH benefited from being HBK's cocksucker backstage buddy, then got the best possible rub in wrestling history (consecutive programs with Foley, Rock than Austin, in which he went over in ALL) then he was given his "prestigeous" reigns after knocking up the bosses skank daughter. Not fair to compare, let alone the glaring, gaping hole between the two's abilities
HBK has had great matches with great workers like Taker, Hart, Owen and Bulldog. He's also had great matches with known stiffs like Nash, Sid, Masters. Triple H's ability to have great matches all depends on who's in the ring with him. Not surprisingly his best matches have come against Austin, Foley, Rock and of course...HBK.
Since HBK's 2002 return his classics with Angle, Jericho, Cena, and Taker have been way better than any of Triple H's matches. The best matches Trips has had in that same span have been with HBK.
HBK is not above working mid-card guys and making them look good and giving them credibility,(Carlito, Masters, Benjamin, and in 2004 an up and coming Orton and Batista) Triple H has squashed anyone not named Cena or Batista at every turn. He has buried many over wrestlers too. RVD and Kane come to mind. HBK was a backstage politicker, but at least he has made things right. Tripps, one would think, would lay down for some guys, since legitimate, proven draws, did it for him to help make him.
I can go on and on, but really it's nonsensical. HBK was better than HHH before he ascended to the upper card, and he's been way better since he returned. Really, there is not a worker in the past twenty years on the North American continent that can be compared to HBK unless that name is Flair. And if we were looking for peers of a similar age thy names would be Misawa and Kobashi.