Few wrestlers have ever made as much of an impact on the wrestling industry as Shawn Michaels did in his career. Michaels is named more than any other wrestler by the current talents who are asked about who inspired them to become wrestlers. The matches of Michaels put him at the highest level of performer in the history of the business.
Not even a nearly flawless wrestler like the Heartbreak Kid had a career without embarrassment. The worst moments of Michaels as a character or as the person performing would not overshadow his greatest times, but they were there. Find out just which memories added some flaws to the icon’s legacy. The following embarrassing moments stand out for the negative in Michaels’ career.
10 JBL Storyline About Him Going Broke
One of the forgotten storylines from Shawn Michaels’ career for good reason featured JBL holding leverage over him. The angle claimed that Michaels had lost all his money on bad investments and declared bankruptcy.
JBL hired Michaels and demanded he followed orders to make enough money back to have a secure life for his family. The storyline was completely made up as Michaels was in good standing at the time. WWE’s bad idea was dropped in time for Michaels to ditch JBL before WrestleMania season.
9 Retiring To Get Out Of Dropping Title
Many of the personal issues and selfish decisions made by Shawn Michaels in the first chapter of his main event run still haunts his legacy. One of the low moments came in 1997 when Michaels retired with the infamous speech about losing his smile.
Michaels was reportedly scheduled to drop the WWE Championship to Bret Hart at WrestleMania 13 one year after Hart put him over. The cheap cop-out hurt WWE’s long-term planning and was allegedly a ruse as Michaels returned to the ring about five months later.
8 Brown Pants Gear
Shawn Michaels almost always had cool gear with the various red and blue color schemes usually leaving a lot of positive reactions from the viewers. However, the gear choice of Michaels during one of the biggest nights of his career ended up being remembered just as much.
Michaels won the World Championship for the last time in his career back at Survivor Series 2002 in the first Elimination Chamber match. For some reason, the fashion choice of brown pants was selected by Michaels and has been mocked for years with fans and wrestlers still joking about it today.
7 Chris Jericho Punching His Wife
The need for wrestling characters to get embarrassed can lead to great storylines. Shawn Michaels and Chris Jericho had one of the best rivalries in WWE history back in 2008. Jericho turned heel to form the most successful character of his in WWE.
The biggest segment to take things to another level featured Michaels claiming he was going to retire at SummerSlam. Jericho was upset about this and tried to swing at Michaels who ducked. The fist hit the face of Michaels’ wife in an uncomfortable moment that made fans want to see Michaels get revenge.
6 Failing As Authority Figure
WWE wanted to continue working with Shawn Michaels when he retired from the ring for real in 1998. Various back injuries would continue to make Michaels’ run end after putting over Steve Austin to stop performing in the ring.
The role given to him to return was the Commissioner position running the show in 1998-1999. Michaels felt out of place and didn’t have the same magic. WWE removed him from the position faster than expected as it wasn’t meant to be.
5 Losing To Hulk Hogan
WWE wanted to book a dream match between Shawn Michaels and Hulk Hogan for the first time at SummerSlam 2005. The match would see two iconic WWE performers finally clashing, but the drama behind the scenes made it a strange dynamic.
Michaels was expecting to put over Hogan at SummerSlam but win a rematch the following month. Hogan changed the plans before the show revealing he wasn’t going to return. Michaels was livid and comically oversold all match. Everything about the scenario provided embarrassment for the legend.
4 MSG Fans Turning On Him For Sid
Diehard wrestling fans typically had the reputation for rallying behind the great in-ring workers and turning against overpushed big men in the ‘90s. That made it even stranger when Madison Square Garden cheered for Sycho Sid over Shawn Michaels at Survivor Series 1996.
Many fans grew tired of the stale babyface act of Michaels. The natural personality of Michaels was an arrogant heel at the time and the New York fans turned against his heel act. This was one of the first instances of the audience completely turning against a top face in WWE.
3 Montreal Screwjob
The Montreal Screwjob changed the wrestling world forever when Vince McMahon ended the Survivor Series 1997 match of Shawn Michaels vs Bret Hart by ringing the bell. Michaels won the match via the sharpshooter even though Hart never submitted.
A wrestler not knowing what would happen in a match was almost never done in wrestling before this. Michaels claimed he had no idea and swore to Bret that night. The reveal came years later when Michaels admitted he was aware before and felt shame for lying all that time.
2 Teaming With "God" Vs The McMahons
Vince McMahon entered a long feud with Shawn Michaels in 2006 as one of WWE’s top programs. Michaels scoring a victory over Vince at WrestleMania 22 was not the end of the feud. The follow-up would see Vince mocking Michaels’ religion after it changed his life during his retirement.
Michaels was forced to team with God against Vince and Shane. WWE had a spotlight show an invisible shadow claiming it was God coming to help Michaels as Vince’s latest attempt at heat. Michaels took part in the angle, but many assumed it wasn’t an easy decision given how he felt about religion.
1 Coming Out Of Retirement For Worst Match Of His Career
Shawn Michaels seemed like one of the few wrestlers who had a great retirement and would never ruin it. Many years passed with tempting ideas like AJ Styles, Daniel Bryan and other incredible performers creating interest for a comeback match of the legend.
Michaels made the move to return for a match in Saudi Arabia where the paydays were significantly higher than any other shows in WWE history. The match of Michaels and Triple H vs The Undertaker and Kane ended up being a disaster. All four men expressed shame and it was considered one of the worst matches of all time.