Shawn Michaels is widely considered one of the greatest in-ring performers of all time. During his over twenty-year-long career, Michaels competed in countless classics, from the ladder match against Razor Ramon at WrestleMania X to his retirement match at WrestleMania XXVI against The Undertaker.
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However, Shawn's career also provided a lot of drama - both behind the scenes and in the ring. There are probably few other wrestlers that so many bad things have happened to - in kayfabe, although often precipitated by real-life incidents. Here then are the ten worst things that have happened to Shawn Michaels in kayfabe.
10 Getting Stripped Of The IC Title (1993)
Shawn's career seemed to be going somewhat well - at least in kayfabe - while he was part of The Rockers. Him and Jannetty won tag team gold in the AWA and made an impact in the WWE. Although never (officially) winning the tag team titles, the Rockers did well for themselves. In early 1992, Shawn finally cut off the dead weight of Marty Jannetty that he felt was holding him down. Within a year, Shawn would be proven right: he won the Intercontinental title from the British Bulldog and headlined Survivor Series 1992 against Bret Hart. Things went great - until Jack Tunney stripped Shawn of the title in September 1993 for failing to defend the title regularly. In storyline, Shawn had missed a few agreed-upon matches, which left Tunney with no alternative, but to declare the title vacant.
9 Having To Vacate The IC Title (1995)
Shawn eventually regained the title in July 1995 from Jeff Jarrett. He was supposed to defend it against Dean Douglas at In Your House 4 but was attacked ahead of the event by a group of Marines. While the incident actually occurred, the scale of it was blown out of proportion on television. Either way, Shawn was not medically cleared to compete and therefore had to hand the title over to Dean Douglas.
8 Career-Threatening Concussion (1995)
Michaels made his triumphant return to in-ring action at the Survivor Series 1995 in a winning effort in the Wildcard Survivor Series match. The next night on Monday Night Raw, Shawn faced Owen Hart. During the match, Owen performed an enzuigiri to Shawn's head. Minutes later, Shawn collapsed in the ring. EMTs came to the ring to check on Shawn and even Owen and his manager Jim Cornette seemed shocked. It turned out that Shawn had suffered a career-threatening (kayfabe) concussion and his career hung in the balance. Of course, Shawn returned two months later at the Royal Rumble and would go on to beat Bret Hart at WrestleMania 12 to win his first WWE title.
7 Knee Injury And Misplacing His Smile (1997)
For most of 1996, Shawn Michaels was on top of the world as the WWE Champion - until Survivor Series, that is, when Sid beat him for the title and attacked Shawn's mentor and manager, Jose Lothario. Shawn vowed for revenge. The rematch would take place in San Antonio's Alamodome at the Royal Rumble 1997 where Shawn would regain his title. A final match between him and Sid was scheduled for a special Thursday Raw Thursday episode of Raw, but Shawn had to forfeit the title suddenly due to a career-threatening knee injury. Much more tragic though was that Shawn also lost his smile. He would return to the ring - smile included - in May.
6 Getting Beat Up By DX And The Corporation (1999)
Michaels retired from in-ring competition after WrestleMania 14 as a result of a legit back injury. He returned to television as the WWE Commissioner in December 1998. He would initially be associated with Vince McMahon's Corporation stable and make DX's life difficult but that would last only for a month.
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The trouble he caused his former friends in DX wouldn't be forgotten, though, even after Shawn turned on McMahon. In January 1999, the Corporation and DX seemingly made a deal and beat Shawn up outside the arena. The bloody and unconscious HBK would be put into an ambulance and not be seen on TV for two months.
5 Stabbed In The Back By Triple H (2002)
After a two-year TV absence, Shawn returned to WWE television in the summer of 2002 and joined the ill-fated WWE version of the NWO. His mission was made clear immediately: bring Triple H into the group. However, Vince McMahon disbanded the group. Thankfully, Shawn had a plan B - reuniting DX. When it seemed that him and Triple H were on the same page, Hunter turned on Shawn and gave him the Pedigree. A week later, Shawn was attacked backstage just as Triple H explained his actions. Hunter vowed to find the culprit - until it was revealed that it was Hunter himself! Triple H had stabbed his best friend in the back. The rivalry would continue until 2006 when, ironically, both men reunited against Vince McMahon and brought back DX.
4 Concussed by Randy Orton (2007)
DX would have a successful reunion until Triple H suffered a torn quad (again) at New Year's Revolution 2007. Shawn would continue to feud with Rated-RKO alongside John Cena. After Backlash, the two sides both disbanded and Shawn continued to feud with Randy Orton. At Judgment Day, Randy would send Shawn on the shelf by punting him in the head. Shawn would not return to the ring until the fall.
3 Eye Injury Forces Retirement (2008)
2008 would turn out to be a terrible year for Shawn Michaels, at least in kayfabe. After retiring his friend Ric Flair, Shawn was accused by Chris Jericho of faking a knee injury. The feud would heat up and Jericho would send Shawn head-first into a monitor on Highlight Reel, causing a detached retina (in storyline).
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The injury would lead to Shawn's wife asking her husband to retire, which he would agree to at SummerSlam 2008 - only to return to the ring as a result of Jericho (accidentally) punching Shawn's wife.
2 Losing All His Savings (2008)
But retirement was not the worst thing that befell Shawn Michaels in 2008. By December, the recession had apparently melted away all the savings that the former multiple time World Champion and regular main eventer had accumulated over his career. As a last resort, he agreed to serve as JBL's personal henchman. The feud would culminate at No Way Out 2009 and Shawn was a free man again - just in time for his WrestleMania 25 classic against The Undertaker.
1 Losing To The Undertaker At WrestleMania 25 & 26 (2009/2010)
Shawn would lose that match against The Deadman in Houston. After the loss, Shawn disappeared until SummerSlam when he returned alongside DX partner Triple H against Cody Rhodes and Ted DiBiase Jr. Shawn's career seemed to be going well, until the Slammy Awards award for 'Match of the Year' in December reminded Shawn of the match at WrestleMania 25. Shawn challenged the Undertaker for a rematch at WrestleMania 26 but the Deadman declined. Shawn would pursue every avenue he could to get the match and finally found it when he cost the Undertaker the World Heavyweight Title at Elimination Chamber 2010. Taker would accept Shawn's challenge on one condition: Shawn had to put his career on the line. The rest is history.
