When wrestling personalities mull over the greatest all-around talents in the history of the business, more often than not, the name Shawn Michaels comes up in the mix. That’s particularly so for talents who were dedicated to WWE. True, HBK got his start working on smaller stages. Once he got started in WWE in 1988, though, it was the only promotion he wrestled for straight through his retirement in 2010 (plus a comeback match in 2018).

Related: Shawn Michaels' 10 Biggest Wins In His Career

Michaels was entertaining and incredibly talented. Moreover, he was one of the influential stars of his generation. HBK also had his moments of undermining his employer, though, via questionable decision making and the direction his life took at some key junctures.

10 The Incident In Syracuse

HBK Concussion

In 1996, Shawn Michaels fell victim to a real life beat down in Syracuse, New York. To this day, details remain sketchy and conflict between accounts, but the general gist of the story was that Michaels antagonized one or more men in a bar who wound up beating him up in the parking lot.

There were heavy implications coming out of the story—even as it was reported in WWE’s own documentary about HBK’s career—that he and the wrestlers with him were at least intoxicated, if not affected by other substances. The result was a dangerous and embarrassing situation that derailed WWE's immediate plans, including Michaels being unable to work a PPV match with Dean Douglas. More importantly, HBK fortunate not to face more permanent injury or even death.

9 Losing His Smile

Michaels Lost Smile

As Bret Hart discussed in his book and a number of other sources have corroborated to varying degrees, WWE’s plan was for The Hitman to face and more than likely defeat Shawn Michaels in the main event of WrestleMania 13, a rematch from the year before. That match didn’t happen because Michaels lost his smile and vacated the title.

Related: 10 Insane Quotes From Pro Wrestling Books

In Michaels’s autobiography, he claimed a knee injury was what truly took him out of action. There’s no shortage of wrestlers who have expressed their skepticism—most notably Hart—with the suggestion that HBK simply didn’t want to put over Hart or anyone else for the title. The promo was ripe for parody and HBK’s handling of the situation, whether he truly was hurt or not, reflected poorly on WWE and its top title.

8 The 1993 Suspension

HBK 1993

1993 saw Shawn Michaels face a suspension for failing a drug test, which caused him to relinquish the Intercontinental Championship. The merits of the suspension remain unclear as HBK denied wrong doing at the time, and has continued to ever since (even while owning up to other poor behavior).

It's possible that WWE actually did wrong by The Showstopper in wrongly suspending him, but if, as it would seem on the surface, Michaels was to blame, it’s another example of him failing the company. Despite getting a solid push as a long-standing Intercontinental Champion, with a bright future, he undermined plans here.

7 Sabotaging Vader

HBK Vs Vader

Big Van Vader was one of WCW's greatest heel world champions, and when he signed with WWE, he looked primed to carry forward in similar fashion. Indeed, between getting a big push and being heavily featured in promotional materials, it seemed the writing was on the wall that Vader would win the WWE Championship off of Shawn Michaels at SummerSlam 1996.

Accounts vary as to what went wrong for Vader, with insiders like Bruce Prichard suggesting he didn’t gel with the company’s plans or meet management’s expectations. Nonetheless, one prevailing narrative contends that HBK himself campaigned against dropping the title to The Mastodon, with complaints ranging from Vader being too stiff, to smelling badly, to more generally not being fit to take the world title. We’ll never know how things might have looked with Vader picking up this win, but based on his success in WCW, there’s reason to believe he could have thrived atop WWE, too.

6 The Curtain Call

Curtain Call

The spring of 1996 saw Diesel and Razor Ramon leave WWE for WCW. For their last show in Madison Square Garden, they shared the ring with real-life close friends and kayfabe rivals Shawn Michaels and Triple H. In an era when WWE still protected the business, this moment was earth-shattering.

Michaels has since claimed that he did get permission from management for what became known as “The Curtain Call.” It seems that, at minimum, the powers that be were conflicted about this unusual scene, even in a house show environment, as it undermined the credibility of the stories WWE told.

5 Crown Jewel 2018

DX Crown Jewel

Shawn Michaels appeared to have accomplished the unlikely when he lost a match with his career on the line and did, in fact, retire. He capped a series of great WrestleMania matches by losing his last one to The Undertaker at WrestleMania 26 and stayed out of action afterward. That is, he remained retired for eight and a half years.

HBK put on his boots one more time for Crown Jewel 2018 in Saudi Arabia. As he discussed in an interview with The New York Post, he viewed the match as less of a comeback or breaking his retirement than a nostalgic reunion with his friends. The match, which saw him team up with Triple H against The Undertaker and Kane, went poorly by just about every metric. To be fair, The Showstopper probably gave the best performance of the match. Even HBK wasn’t able to beat father time and pull out a performance that would redeem this debacle of a match.

4 Substance Issues

Shawn Michaels WrestleMania 14

In WWE’s Heartbreak & Triumph documentary about Shawn Michaels, he was open about how issues with painkillers and recreational substances impacted his attitude, performance, and lifestyle. Paired with ego issues, Michaels became difficult to work with during his original time at or around the main event level in WWE, and even less pleasant when he worked in part-time, non-wrestling roles.

While wrestling is full of outlandish characters and poor behavior can be considered par for the course at times, Michaels let his personal issues affect his work and arguably made him an embarrassment for the company for a period of time.

3 The “Sunny Days” Promo

Sunny HBK

In one of Shawn Michaels’s most infamous promos, he said Bret Hart was having some “Sunny days,” in a thinly veiled suggestion that The Hitman was having an affair with Sunny. Hart wrote about it in his book, noting that not only were the allegations false but they caused strife in his already strained marriage.

Related: Every Version Of Sunny, Ranked From Worst To Best

This cheap shot at Hart was unprofessional and contributed to unnecessary drama as Hart and Michaels shared space atop WWE. (It’s even more obnoxious given that—if Sunny is to be believed in shoot interviews—Michaels was actually having an affair with her.)

2 Not Having The DX Spirit For The Reunions

DX Reunited

In 2006, D-Generation X came back to life as Shawn Michaels and Triple H teamed up as active wrestlers for the first time in over eight years. The reunion, which extended and was revisited over the four years to follow (in addition to an angle in 2018) created some memorable promos and solid tag team action. However, a lot of the old DX magic was gone.

Some of the reunited DX’s limitations had to do with both principle players being older, besides the notable absence of other key contributors to the stable’s chemistry. However, HBK himself was a part of limitations. While his Born Again Christian lifestyle undeniably helped his personal life, it also meant that him working the rebellious, juvenile DX gimmick wasn't a fit and fell flat with long-time fans.

1 Not Joining The Part Time Mix

Goldberg Lesnar Survivor Series

The general consensus among wrestling fans seems to be a respect for HBK making his retirement mean something—saying that he was going away in 2010 and actually meaning it. However, in the contemporary wrestling landscape full of legends who work part-time, Michaels has been notably missing form the mix.

HBK was a great enough in-ring worker and talker to make complete sense as a part-time act in modern WWE. Michaels not contributing has cut out a surefire draw WWE might have had, not to mention someone who’d probably deliver at a higher level than most of the talents who come back well past their primes.

Next: 7 Times Shawn Michaels Said No To Vince McMahon