Shawn Michaels wrestled consistently for WWE, formerly the World Wrestling Federation (WWF), from 1988 until his first retirement in 1998. He held non-wrestling roles from 1998 to 2000 and resumed wrestling in 2002 until retiring ceremoniously in 2010, before being assigned as a trainer in 2016 and returning for one match in 2018.
HBK is a four-time world champion, having held the WWF Championship three times and WWE's World Heavyweight Championship once. He is also a two-time Royal Rumble winner (and the first man to win the match as the number one entrant), the first WWF Grand Slam Champion and the fourth WWF Triple Crown Champion, as well as a two time WWE Hall of Fame (2011 as singles wrestler and 2019 as part of D-Generation X).
In the latest edition of his podcast, WWE Hall of Famer Jim Ross (JR) recalled Shawn Michaels’ personal issues in the late 1990s: “You can’t let guys go and just walk on their contract when they feel like they want to leave … At that time he was [ill-equipped to handle his position in the company].
At that time he was, because again, you make a lot of decisions under stress. Depression sets in on a lot of things, these performers. And you add either drugs and/or alcohol abuse, you know, self-medicating, prescription meds, all this other crap”.