Top 15 Worst Wrestlers Shawn Michaels Ever Had To Work With

It’s hard to find a lot of results when putting “Shawn Michaels” and “bad match” together in an online search. That’s not to say that the Heartbreak Kid was perfect, but he usually was able to put together a good match any given night. Many of us who grew up watching wrestling either in the Attitude Era or the Ruthless Aggression Era know Michaels to be one of the best in-ring performers in World Wrestling Entertainment history.

Many of his best matches feature legendary names like Razor Ramon, “Stone Cold” Steve Austin and, in his final match, The Undertaker. There’s a reason why Michaels was given the nickname “Mr. WrestleMania.” However, not all of his matches were five-star quality and there were opponents who weren’t able to perform at the same level that Michaels was able to for a little more than 25 years in the world of professional wrestling.

The list of his lackluster opponents include names who may have had high hopes when starting out in the WWE and then fizzled out quickly. There are also some legendary names in the WWE who faced the Heartbreak Kid during a rough part of their careers. In any case, here are the 15 of the worst wrestlers with whom Michaels had to work.

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15 John Cena

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This might be one of the more controversial posts, but there was a time in WWE history when John Cena was the most boring wrestler in the ring. There are still some who claim that even with decent matches against the likes of Kevin Owens, Sami Zayn and AJ Styles; a number of wrestling fans are not likely to enjoy Cena in the ring. He did face off against Michaels for the WWE Championship at WrestleMania 23 in a match where it was entertaining but the two exchanged words during the match.

Michaels was always known for being a perfectionist in putting on a show for the fans, and had some words for Cena regarding the fact that Cena didn’t sell the work that Michaels had done on his leg early in the match. The two have since had some decent matches, including a nearly hour-long match on Raw after their WrestleMania bout. The jury is still out on whether Cena is one of the best wrestlers in history.

14 El Matador

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Tito Santana had a pretty successful run with the WWE during the 1980s and early 1990s, but was repackaged as El Matador where he wore a full suit usually worn by Spanish bullfighters. He would face Michaels in a singles match at WrestleMania VIII at the Hoosier Dome in Indianapolis, Ind. It was not one of the best matches of the night as it was very mediocre because both men were capable of doing so much more in the ring.

Santana, I mean The Matador, spent a good portion of the match keeping Michaels in a headlock. This slowed the match down and it felt like the 10-minute bout lasted an eternity. It wasn’t the best start to a WrestleMania, but it could have been a lot worse. Santana claims that the WWE missed an opportunity with making The Matador character work, but mediocre matches like this one probably doesn’t help his case.

13 JBL

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Let’s forget the fact that the story line about how John “Bradshaw” Layfield pretty much owned Michaels due to financial difficulties because it’s hard to believe that Michaels was hurting financially during the final years of his WWE career. The match these two had at No Way Out in 2009 was at best an average match where Michaels was essentially the one telling the story through his emotions and actions.

JBL was not at his best after being the longest reigning champion of SmackDown history. Most of his offense was strikes, which comprised the majority of his move set throughout his career. There are many people who believe that JBL was one of the most overrated wrestlers to hold the WWE Championship. There was a reason why JBL didn’t hold many titles after dropping the belt to John Cena back at WrestleMania 21. For a match between two champions, only one was showing the skills worthy of a title.

12 Vladimir Kozlov

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Usually, John Cena is the person who is credited for ending undefeated streaks and main event pushes for talents like Umaga, Wade Barrett and others. But Shawn Michaels could be blamed, sort of, for the beginning of the end for Vladimir Kozlov. The Russian heel was never pinned in singles matches for nearly a year before an episode of Raw in March 2009 where Michaels was able to defeat Kozlov – this time to decide who was going to face The Undertaker.

It’s a good thing that we ended up with Michaels vs. Undertaker at WrestleMania XXV that was a showdown of epic proportions. Kozlov was very one-dimensional and was another example of a powerhouse that the WWE wanted to push until they discovered the wrestler’s limits on the microphone and in the ring. At least we saw a funnier side of Kozlov before he was released from the company in 2011.

11 Rob Conway

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Just looking at Rob Conway and one can tell he wasn’t the worst wrestler of all time, nor even the worst in the WWE’s original brand split era as he was part of a tag team with Sylvan Grenier in La Resistance – and enjoyed a WWE Tag Team Championship reign. But Conway by himself was never really an impressive talent in terms of in-ring abilities and speaking on the microphone.

He had a mediocre match on Raw one-on-one with Michaels in March 2005, but he also teamed with Grenier to face Michaels and a returning Marty Jennetty in another loss to the reunited Rockers. Michaels also got the better of Conway with the infamous “May 19” referee shirt before Conway wrestled Kane in a squash match in favor of the Devil’s favorite demon. In the end, Conway felt a lot like a Buff Bagwell copycat. Need confirmation? Just look at him.

10 Ted DiBiase, Jr.

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Michaels has had a number of matches with the Million Dollar Man in Ted DiBiase in the 1990s, but he also wrestled his son – Ted DiBiase, Jr. – as part of the D-X vs. Legacy storyline that took place in 2009 that featured the two teams facing off at SummerSlam 2009, followed by a submissions count anywhere match and a Hell in a Cell match to finish the feud. The thing was that the second-generation WWE superstar did not have much of his father’s in-ring charisma.

In fact, the younger DiBiase was about as boring as paint drying on a block of wood. He formed a tag team with Cody Rhodes to win the WWE Tag Team Championships in the beginning of his career, but wasn’t able to do much after splitting up into a singles superstar. The WWE even tried to bring back the Million Dollar Championship, which did nothing for DiBiase. Eventually, he chose not to re-sign with WWE and left wrestling in 2013.

9 Batista

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Here are two superstars who faced one another multiple times during the original brand split era as Batista was evolving into the WWE’s next powerhouse main event talent. It seemed like a great idea to have the two face each other in matches since Michaels is a veteran who could help put over the Animal and also help build a high-quality match for the fans. Their matches included a singles match at Armageddon 2003 and Backlash 2008. There was even a lumberjack match on an October 2008 episode of Raw.

While he was definitely a strong wrestler, he was never really as talented in the ring as someone like Michaels. Over the years, his in-ring skills diminished and he has been booed multiple times in recent years. There may have been a time when Batista could have been the next Goldberg or Brock Lesnar. Then again, that might have been the problem.

8 One Man Gang

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One of Michaels’ earliest matches of his professional wrestling career came in the old WCCW against One Man Gang in January 1985. It was a short match where Michaels was essentially the jobber where the very large and very powerful giant was booked to look dominant. The two would run into each other multiple times, granted with much different gimmicks in the WWE. While Michaels had come to WWE as part of a tag team with Marty Jannetty in the Rockers, One Man Gang had been transformed into Akeem – embracing his African roots in one of the most absurd vignettes in wrestling history.

At WrestleMania V, Akeem and the Big Boss Man (also known as the Twin Towers) defeated Michaels and Jannetty. Both Michaels and Gang had separate career paths after that event. Overall, the One Man Gang was one of the big men in wrestling history who was not able to climb the ranks of the match card, never capturing world championship gold in WWE or in WCW.

7 Gene Snitsky

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Gene Snitsky was a large man, but was never originally meant to be a main roster wrestler right away until the match with Kane that led to the accidental loss of Lita’s baby in late 2004 led to him being kept on Raw. But he would have multiple character changes that included being placed as an enforcer for Edge, a tag team with Tyson Tomko, another tag team with Goldust and finally shaving his hair and face and having discolored teeth.

Somewhere in between all of that was a singles match on a December 2005 episode of Raw and it was more of a match to give Michaels a win. There were other times where Snitsky teamed with Umaga to face DX in 2006 and 2007. Snitsky is another example of one of those larger talents who may have been rushed in his development to joining the main television roster.

6 Mike Knox

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The ECW brand in the WWE had a number of large figures and other athletes who were not necessarily ready for television, but the WWE officials wanted to bring up from the development territories in some way. Mike Knox is one of those guys who might have been rushed a little too quickly and he didn’t really have much going for him other than being the jealous giant boyfriend of Kelly Kelly.

When part of the Survivor Series match in 2006 as a member of Team Rated RKO to face off against Team D-X, he was getting in Triple H’s face for flirting with Kelly Kelly. Michaels would deliver Sweet Chin Music and looked confused, seemingly not aware that Knox was in the match. Fans could see him walk over to the corner asking “Who was that guy?” Knox’s career in the WWE would involve defeating jobbers but struggling against other peers on the main roster before his release in 2010.

5 Salvatore Sincere

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In the 1990s era of the WWE, there were some interesting characters seen on television that hit all walks of life. Salvatore Sincere was one of them as he spent nearly three years with the company. One of his earliest matches was against Michaels in November 1996 during an episode of Superstars. For a good part of the match, Sincere was in control as the cocky, arrogant heel before Michaels had a rally that ended with HBK hitting Sweet Chin Music in less than 10 minutes.

Outside of this match, Sincere wasn’t really able to make a big impact in the WWE. He had a feud with Marc Mero to win the valet services of Sable. Mero would call him out by his real name of Tom Brandi, which would be carried over for the rest of his WWE run in 1998 in a loss to Jeff Jarrett on Raw.

4 Johnathan Coachman

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Before joining ESPN and helping bridge the gap between the WWE in Stamford, Ct., and the sports media giant in Bristol, Ct., Johnathan Coachman was one of the Ruthless Aggression era’s commentators that was brought into the ring every once in a while. Now the WWE was always known for bringing commentators into the ring everyone – not counting Jerry “The King” Lawler since he was a full-time wrestler before joining the WWE broadcast team.

The problem with commentators being in-ring competitors is that they usually are never really as good as a full-time wrestler. That’s just a fact. Coachman would repeatedly need assistance from others, like the Spirit Squad in a match with Michaels on an episode of Raw in March 2006. Another mediocre match through no fault by the Heartbreak Kid. But that didn’t stop the Coach from being involved in multiple matches where he was either being beaten up like a jobber or barely winning thanks to another heel.

3 The Spirit Squad

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It was previously talked about how the Spirit Squad were one of the worst tag teams in WWE history. They were easily one of the most disliked teams in 2006 and were helping other heels win matches that maybe they should have had no reason to be in the ring – i.e. Johnathan Coachman. The Spirit Squad had been part of the feud with Michaels in early 2006 and it would eventually lead to the reunion between HBK and Triple H to reform DX.

Over several months, the Spirit Squad transformed from WWE Tag Team Champions to becoming jobbers that were fed to the DX team that eventually fit all five members of the faction into a box marked for being shipped to Ohio Valley Wrestling. While there was talent with the now Dolph Ziggler and Kenny Dykstra – who would later be released from the WWE in 2008 – the other three members didn’t have a lot to bring to the table.

2 Gary Sabuagh

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In a January 1995 episode of WWE Superstars, Shawn Michaels carried a faux Intercontinental Championship to the ring during a match with Gary Sabaugh – known to many as the Italian Stallion. This was a point in his career where he had some experience with WCW and the National Wrestling Alliance, but was nowhere near his prime as he was about 37 years old. The match itself was one-sided to help put Michaels over and lasted approximately five minutes in total.

While with the WWF, Sabaugh played an intrigal role in the Matt and Jeff Hardy getting a chance to join the WWF in the mid-1990s. He would charge an appearance fee for them to work as jobbers and was scheduled to meet with them in North Carolina before going to a WWF show in Georgia. According to reports from Matt Hardy, Sabaugh left them stranded and collected the money – an incident that was part of why he was fired from WWF.

1 Hulk Hogan

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While the leader of Hulkamania can be considered one of the most iconic wrestling superstars in the 1980s and 1990s, Hulk Hogan started to decline in the final years of his wrestling career. Hogan was not on a full-time contract when he was billed to compete with Michaels in a feud that would lead to a match at SummerSlam in 2005 – a match that was billed as the first-ever meeting.

Thankfully, it was the only meeting. Hogan was not on television for many of the weeks leading up to the pay-per-view and Michaels oversold many of the moves that Hogan has done for years – essentially mocking that Hogan is made to be a powerhouse with simple moves. It was considered a dud of a match for obvious reasons. Michaels would later comment it was supposed to be a best of three series and it shouldn’t take much investigation to see why it ended up being a one-time only occurrence.

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