Triple H

Hunter Hearst-Helmsley entered the World Wrestling Federation in 1995. He came from Greenwich, Connecticut, and consistently reminded everyone that he was much more higher-class than they were. During this time, he held the Intercontinental Championship on several occasions. But after two years, Triple H made friends with Shawn Michaels, and the two began a group of rebellious, sophomoric wrestlers called D-Generation X. Helmsley captured the European Championship from Shawn Michaels in December, following a mock of a match ordered by then-WWF Commissioner, Sgt Slaughter. Following Shawn's departure due to injury, HHH took over the faction, bringing in X-Pac, Road Dogg and Billy Gunn. It was Helmsley's eventual betrayal of the group at Wrestlemania XV, almost exactly one year after rebuilding it, that led him on the path to his first WWE Championship, in August of 1999, defeating Mick Foley.

DX re-formed in late 1999, now acting as Helmsley's lackeys. The group dissolved again in 2000, but Triple H was now a three-time WWE Champion, and allied himself with Stone Cold Steve Austin, with whom he won the WWE Tag Team Championship, making Helmsley the company's second-ever Grand Slam winner (winning the European, Intercontinental, Tag Team, and WWE Championships) after Shawn Michaels. A quadriceps tear in spring 2001 kept Helmsley sidelined until January of the following year, where he returned to win the Royal Rumble match and defeat Chris Jericho for the WWE Undisputed Championship at Wrestlemania X8. He lost the belt to Hulk Hogan shortly thereafter, but was awarded the World Heavyweight Championship in September of 2002. That title seemed to be superglued around HHH's waist, especially after he formed the faction known as Evolution, with former 16-time World Champion Ric Flair, and up-and-coming stars Randy Orton and Batista. It took upwards of two years before Evolution finally dissolved, Helmsley winning more World and WWE Championships along the way. In 2006, he and Shawn Michaels reunited to re-form DX, until another injury sidelined Helmsley for most of 2007.

Triple H was drafted to Smackdown in 2008 taking his WWE Championship with him. He went back to Raw in 2009, bringing his again-newly-won WWE Championship back to the "Red Brand," and remained a mainstay of the WWE's main event scene, until he lost to The Undertaker at Wrestlemania 27.

In July of 2011, Triple H was named Chief Operating Officer of the company. He still occasionally gets in the ring, but is now a figure of authority within the company.

Over the course of his career, Helmsley has won 8 WWE Championships, 5 World Heavyweight Championships, 5 Intercontinental Championships, 2 European Championships, 2 Tag Team Championships (once with Stone Cold, once with Shawn Michaels), and won both the King of the Ring Tournament and a Royal Rumble match. He is amongst the most-decorated Superstars in WWE history.

WWE Champions
Triple H defeated Sycho Sid in the opening round, but lost to Hulk Hogan in round 2.

World Heavyweight Champions
Triple H entered the second round of this list as an Alternate, replacing the tying Kevin Nash and Sheamus from round one. He faced off against The Undertaker, and was hastily defeated.

WTF
Triple H defeated Taki in the first round, but was eliminated by The Flash in round 2.