For starters, the term "grand slam" for today's wrestlers is completely irrelevant since the WWE has FIVE titles floating around the men's division - and that doesn't take into account the two defunct titles (Euro and Hardcore.) Just as we don't refer to John Cena as a Triple Crown Champion (WWE, US, Tag champ), why should I refer to anyone as a Grand Slam Champion? The point is that neither designation represents what it was originally intended to represent: That a wrestler had captured every active championship in the company.
The WWE made the Grand Slam status obsolete in May 2001 when - according to Wikipedia (I don't really remember this) - the WWE said the Hardcore Title was a valid substitute for the European Title in terms of achieving the status. Why would the WWE maintain the term Grand Slam - synonymous with FOUR - when they had five active belts floating around? Seems dumb to me.
The WWE has continued to be very sheepish in their definition of Grand Slam status. They have since updated it to acknowledge that a World Title is as good as a WWE Title but they still refuse to acknowledge the existence of the US Championship. Again, why can't the WWE just RE-DEFINE the damn status to acknowledge all the active titles? Wasn't that the concept when they went from Triple Crown Champion to Grand Slam Champion ... to acknowledge that they had FOUR belts?
This might be a little controversial - but given that today's ACTIVE titles include the WWE Title, World Title, IC Title, US Title and Tag Titles ... then I believe the only three wrestlers that fit the status of what the Grand Slam Championship is SUPPOSED to represent would be Chris Jericho, Kurt Angle and Edge.
However, I will actually acknowledge wrestler's that won the WWE, IC, Euro and Tag Titles before May 2001 - when the WWE ridiculously acknowledged the Hardcore Title as anything more than a comedy relief prop - as true Grand Slam Champions ... The only two wrestlers that actually accomplished that were HBK and Triple H.
Of those two, I give the nod to Triple H in a landslide.
Look at HBK. Two of his three IC Title reigns ended with him forfeiting the belt, and one of his three WWE Title reigns ended with another forfeiture of the belt. Michaels might be the best wrestler of all time, but he was a pretty shitty champion in my opinion.
Now, before people some young kids try to say that the way a wrestler loses a belt is irrelevant because wrestling is scripted ... realize that none of HBK's forfeitures were scripted. The first time he vacated was because of a drug suspension. The second forfeiture was either due to him getting his ass kicked at a club or his refusal to lose to Shane Douglas, whichever you want to believe. His WWE Title forfeiture was either due to a career-ending knee injury or his refusal to drop the belt to Bret Hart at WrestleMania 13 - again - whichever you want to believe.
On top of it, I'm a big believer that HBK ONLY won the European Championship so that the WWE could "re-write" its own history. Consider this, according to Bret Hart's autobiography, VKM told him on September 22, 1997 that he would be breaching his WWE contract. I don't think it's a coincidence that just days prior, Shawn Michaels won the European Title ... and that later that night (it was a Monday), HBK referred to himself as the first Grand Slam Champion, thus eliminating the term Triple Crown Champion, which was an honor held only by HBK, Hart and Nash. With Nash in WCW and Hart seemingly on his way, the WWE coined a new term so they wouldn't have to recognize those two.