When you’ve built a multimillion dollar global company like Vince McMahon has, you tend to have a lot of successes to hang your hat on at the end of the day. No matter how bad of a day it’s been, McMahon can look upon his empire and feel like he ultimately made a fair amount of right decisions along the way. However, just as those with many friends tend to have a lot of enemies, anyone who has achieved as much as Vince McMahon must surely be able to think back on quite a few regrets. In the specific case of Vince McMahon, you have to believe that many of those regrets involve specific characters he’s created over the years.

The wrestling business is no stranger to awful gimmicks, but there is a difference between a bad character and one that goes down in history as one of a company’s biggest errors. The characters that keep Vince McMahon up at night aren’t just the ones that can easily be described as simply awful gimmicks, but also those who were so bad that they threaten to topple Vince’s empire. These are the top 15 characters that Vince McMahon regrets the most.

15 15. Rodney Mack of Thuggin & Buggin Enterprises

Oh man, we’re willing to bet that most of you have already forgotten about this one. The Thuggin & Buggin stable was a group of ECW African American wrestlers managed by Teddy Long. They were a bit like the Nation of Domination in that they were presented as militant types fighting the man. The difference is that the Nation of Domination eventually clarified that their cause wasn’t a white thing or black thing. They were just fighting the power. The Thuggin and Buggin stable never made such a clarification. In fact, Teddy Long would often talk about how they were going to “kill whitey.” For obvious reasons, Vince probably regrets giving the green light to this stable. He probably really regrets it ever since stable member Rodney Mack sued the WWE for racism over the gimmick.

14 14. Meat

One of the best things about the Attitude Era was that there were seemingly no limits on what WWE’s creative team were allowed to try. One of the worst things about WWE’s Attitude Era was that there were seemingly no limits on what the creative team were allowed to try. That’s how we ended up with characters like Meat. Meat was the name of a character played by wrestler Shawn Stasiak who is best described as a sex slave. He was the muscle for the all-female group Pretty Mean Sisters and would often become tired during a match due to sexual exhaustion. Against all odds, WWE got months of storylines out of the Meat character. Somehow, each new storyline was even worse than the last one.

13 13. Naked Mideon

By all accounts, Vince McMahon has a very childish sense of humor. He loves it when people get thrown into pools, when someone farts, or when someone makes an obvious pop culture reference to something that happened at least 20 years ago. Sometimes, however, Vince does seem to realize that he’s gone too far with his particular style of humor and should have taken the advisement of others. You have to believe that’s the case with Naked Mideon. Naked Mideon is the name given to the stage of wrestler Dennis Knight’s career when he decided to stop being a Ministry of Darkness servant and take up stripping instead.

Yes, Knight would go out to the ring and remove his clothes before dancing around for a bit. The joke was that Knight was fat and shouldn’t be wearing such little clothing. Yes, that was the joke.

12 12. Friar Ferguson

Some gimmicks are historically regrettable because they are offensive. Others achieve that status by virtue of being simply bad. Friar Ferguson is one of the best examples of the latter. Friar Ferguson was brought into WWE during the company’s awkward mid-90s period when they were trying to be kid friendly and were struggling to come up with memorable characters. For some reason, it was decided that what WWE really needed was a wrestling monk. You’ve never seen a gimmick die faster than this one. Ferguson barely looked like a wrestler and, for reasons that nobody is quite sure of, came to the ring wearing a yellow writing pad around his neck that had “monk” scribbled on it. This is one of many gimmicks from this era that Vince would like to forget about, but it certainly stands out as one of the absolute worst.

11 11. "Baby Killer" Gene Snitsky

Okay, if we’re being fair, Gene Snitsky only really killed one baby. However, when it comes to such things, one incident is more than enough to earn you the gimmick of baby killer. This goes back to that awful storyline WWE ran involving Kane molesting Lita and getting her pregnant. Eventually, Snitsky was inserted into the mix to take part in a story involving him causing Lita to have a miscarriage. That should have ended this storyline, but instead, someone thought it would be a good idea to have Snitsky continue to mock Lita about her miscarried child. The miscarried child that he was responsible for, mind you. While we agree that baby killers make for effective villains, Snitsky’s character is certainly a candidate for the lowest low in WWE creative history.

10 10. Creepy Heidenreich

When Jon Heidenreich joined WWE, we wonder if they told him exactly what they had in mind for his character. We would venture a guess that they did not. After all, how desperate would you have to be for a job in WWE to agree to play a rapist? Yes, for a brief period in 2004, Heidenreich became obsessed with trying to rape Michael Cole. Typically, this consisted of reading him strange poetry and then trying to drag him to the bathroom to assault him. The really weird part about this whole storyline is how open WWE were regarding it. At no point did they try to present this angle as anything less than what it was. Stephanie McMahon even admitted that the idea was inspired by that classic pawn shop scene in Pulp Fiction.

9 9. Beaver Cleavage

Generally speaking WWE and Vince McMahon don’t own up to their creative mistakes that often. The surest way to tell if anyone actually regretted a decision was to see if a particular character or storyline was immediately dropped after it was introduced. That’s pretty much how we know that Beaver Cleavage was an out and out disaster for WWE. We’d love to give you some insight into what the Beaver Cleavage character was about, but we’re not sure we understand the attempt. It appears that WWE wanted to allege that Beaver and his mom were a ‘50s style family that just happened to be sleeping with each other. Vince and co. caught a lot of flack for this one and decided to drop the character in the classiest way possible; a domestic assault storyline.

8 8. Kerwin White

It’s rare that you get to offend two races with a single character, but Kerwin White is a special kind of character. Perhaps as part of some punishment, Chavo Guerrero was forced to become...well, basically a white guy. He started to wear khakis, go golfing, and other things that rank among the most stereotypical white activities you can imagine. This gimmick was awful partially because it was just stupid, but mostly because it forced a proud Mexican wrestler to start prancing around like a white a guy in order to participate in some comedy sketches and some really awful matches. As a one-off appearance, Kerwin White may have been forgivable, but the character lasted for months even though the joke only really lasted a minute.

7 7. Saba Simba

Speaking of offending races of people, we come to Saba Simba. Now, we’re not going to try to claim that certain racist characters are more offensive than other racist characters, but there are some characters of that type that just go way over the top in a way that people of all races recognize is is just ridiculous. That was the case with Saba Simba. To be honest, WWE had done tribal African gimmicks and most of them have gone by without drawing too much heat from concerned fans. Saba Simba was different. Maybe it has to do with how blatant the character was. Maybe it was because Simba debuted in the 90s. Maybe because it was Tony Atlas, a previously established star, having to portray such an awful gimmick. Whatever it was, audiences took one look at Saba Simba and immediately rejected it. The character is almost never referenced.

6 6. Fake Razor Ramon and Fake Diesel

Vince loves to put out content that makes WCW look like complete idiots. He never likes to acknowledge just how long WCW beat WWE in the ratings, nor how desperate WWE got to beat WCW during their prime. He really never likes to bring up fake Razor Ramon and fake Diesel. If WWE had simply trotted out these obviously fake characters in order to make fun of Scott Hall and Kevin Nash, they may have not been so bad. Instead, they hyped these characters up for weeks as being the actual wrestlers and then spent a few more weeks treating them like actual stars. This booking strategy backfired horribly as fans tuned out in droves when they realized what was going on. Vince couldn’t have been happy that he sent thousands of viewers to WCW.

5 5. The Greater Power

In 1999, WWE ran an angle involving Undertaker’s Ministry of Darkness and a mysterious “Greater Power” that even The Undertaker had to answer to. For weeks, millions watched as WWE teased the arrival of this higher power. When the character finally appeared on television, it was revealed that the greater power was Vince McMahon. That reveal essentially invalidated weeks of storylines and immediately brought an end to one of WWE’s hottest angles at the time. The only reason Vince even played the greater power is because he rejected the guy that was originally supposed to play the character - Christopher Daniels - and WWE weren’t able to sign a big star from WCW to jump ship and play the character instead. This was one of Vince’s many failed projects and the one that most fans will unfortunately never be able to forget.

4 4. Muhammad Hassan

The initial version of the Muhammad Hassan character was actually pretty brilliant. He was an Arab-American wrestler who was angry at fans for perpetuating post-9/11 stereotypes about his heritage. He was technically a heel because of this, but he was the kind of heel that people could sympathize with because they understood his motivations. At some point, WWE apparently got tired of this particular heel character and decided to just make Hassan an actual terrorist supporter. At least that’s what we think happened when Hassan had a group of masked operatives beat up The Undertaker and choke him with piano wire. Oddly enough, nobody in WWE seemed to realize that this was a terrible idea until the London bombings occurred a few days after this event. This character turn was pretty much wiped from WWE history after that.

3 3. Iraqi Sympathizer Sgt. Slaughter

You have to believe that the decisions Vince McMahon regrets most are the ones that lead to him losing money. In terms of characters, there are few that lost Vince McMahon more money than Iraqi sympathizer Sgt. Slaughter. In order to capitalize on the Gulf War, McMahon decided to turn Sgt. Slaughter into a heel Iraqi supporter. McMahon thought that millions would tune in to watch the very American Hulk Hogan battle this evil turncoat at WrestleMania VII. So, he set the storyline in motion and booked the L.A. Coliseum for the upcoming event.

Fans immediately recognized that Vince was essentially trying to profit off of the war and immediately changed the channel. WWE was forced to move their biggest show of the year to a smaller stadium - they later claimed it was due to security concerns - and WrestleMania VII suffered one of the worst buyrates in WrestleMania history.

2 2. Alcoholic Road Warrior Hawk

WWE never really did much with the Legion of Doom during their initial WWE run. As the Road Warriors, Hawk and Animal became one of NWA’s biggest draws and most infamous acts. However, they just kind of became yet another tag team in WWE. For some reason, WWE decided to bring back Hawk and Animal during the Attitude Era even though both wrestlers were well past their prime and WWE clearly had no stories in mind for them. During this failed run, the company decided to capitalize on Hawk’s real-life addiction problems by turning him into an on-screen drug and alcohol addict.

Whatever dignity this storyline could have had immediately went out the window during an on-screen segment in which Hawk was seemingly killed by Droz during a suicide attempt. It was just as bad as it sounds.

1 1. Suicidal Tim White

You know, of all the awful storylines and characters WWE have featured over the years, few were quite as bad as suicidal Tim White. Don’t remember this character? We’re not surprised. Most fans have tried to block it from their memory. For reasons unknown to anyone, WWE decided to turn longtime referee Tim White into a suicidal character. At first, White tried to shoot himself with a shotgun. After that failed, WWE ran a weekly - yes, every single week - segment called the Lunchtime Suicide Series. Each of these segments featured White trying to kill himself in some new and horrible way. He ate rat poison, threw a toaster into a bathtub, and even cut his own wrists which resulted in comically over-the-top blood sprays.

The whole thing resulted in Tim White shooting Josh Matthews. Given the sheer amount of backlash these segments resulted in, it’s highly unlikely there’s a single character Vince regrets more than suicidal Tim White.