Trips' 2 Best Matches:
6 Man Elimination Chamber - World Heavyweight Championship: Summerslam 2003
I am probably going to get some red rep for this, but I could care less. This match is my favorite of all time, and Trips' performance is essential to its quality. He does NOTHING. That's right....NOTHING during the entire match except hide out in his pod, get superkicked in the pod, get totally dominated by Goldberg, only to use the sledgehammer on Goldberg to pick up the win in classic heel fashion. I mean, Goldberg STEAMROLLED through the rest of the competition (including a sickening spear on Jericho through plexiglass)...having him TOTALLY built up to pick up a freaking energetic and massive win for the title. Then, Trips, with his sledgehammer, sucks ALL of the positive energy out of the building and turns it into absolute heat on himself. Classic, classic, classic. That's why Trips is in contention (if not the front-runner) for best heel of all-time.
Triple H v. Cactus Jack - Street Fight - WWF Championship: Royal Rumble 2000
This match sometimes gets overlooked by the circus-like Hell in a Cell match at No Way Out, but this is another classic heel display by Triple H. The majority of the match just consists of him completely obliterating Foley, using chairs, a barbed wire 2x4, and the best of all...handcuffs. The handcuffs really bring out the sadistic nature that Triple H's character was trying to display at the time...showing absolutely no mercy to a highly crowd-favored and sympathetic Cactus Jack. Then after Foley broke free from the cuffs, back-body-dropping Cactus onto thumbtacks, and unsuccessfully pinning Foley after a normal Pedigree, Triple H goes to another level of sick when he Pedigrees Cactus onto the thumbtacks. I remember watching that and legitimately cringing. It just makes you think, "Wow. Triple H is nothing a but a sick *&(%^&&^!!!"