Sports

30 Shadiest Individuals In All Of Sports History

Darren Ryding - March 13, 2024

Sports

30 Shadiest Individuals In All Of Sports History

Darren Ryding - March 13, 2024

People love sports partly because they provide escapism from the grind of daily life. This comes from competing and also from being a sports fan. Unfortunately, not everybody has this mindset. Some characters exploit sports to make as much money as possible. So today, we looked at 30 of the shadiest people in all sports.

This list includes athletes who were serial drug cheats. There are also evil owners who lie to their fans. Then there is the notoriously seedy world of combat sports. These are the worst because they take it to a whole new level. Check out our list below via GQ.

30. Robert Kraft

The longstanding owner of the New England Patriots, Kraft is undoubtedly an efficient businessman. He mostly avoided the embarrassing antics of Jerry Jones and Dan Snyder until 2019. Then, Florida prosecutors hit him for soliciting sexual favors at a massage parlor in Fort Lauderdale. However, in one of the shadiest decisions on this list, the judge ordered video footage from the parlor to be destroyed.

Meanwhile, the underpaid masseuses suffered the consequences of their actions. Kraft escaped scot-free because he has expensive lawyers. In terms of football, Kraft’s regime oversaw some of the biggest scandals in modern NFL history. These include the DeflateGate scandal, SpyGate, and Aaron Hernandez’s murder case. While Kraft obviously isn’t responsible for everything, his leadership doesn’t help.

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29. Bob Arum

Arum is one of boxing’s oldest promoters and shadiest figures. The veteran Top Rank CEO attracted the attention of the FBI on numerous occasions because of potential match-fixing. This included Oscar De La Hoya’s fight against Shane Mosley. Other boxers were involved in this investigation and it was messy for Arum. He’s all about the money and doesn’t care about anything else.

He is one of the main reasons why Terence Crawford hasn’t fought Errol Spence Jr. Meanwhile, Arum has no issue working with alleged drug cartel boss Daniel Kinahan because “nobody was killed at my fights.” At the end of the day, the bottom line is the most important factor in Arum’s life. There’s no doubt about his success and his ruthlessness, but he also alienated himself from many top stars.

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28. Fiorentino Perez

Real Madrid is one of the two biggest soccer clubs in Spain. Their club president, Perez, is also one of the most powerful figures in European sports. However, his influence is pernicious. Genuinely feared in Spain, he is a bullying and overbearing leader. In 2021, he attracted scorn after his attempt to create a European Super League. This turned him into a laughingstock around the continent.

Perez wanted to make a league just for the biggest clubs in Europe. It would have guaranteed them maximum profits. It was a symbol of hubris and greed. In the end, fans turned against him and all of the other club owners involved. He failed in his efforts to consolidate this league and became a joke figure. It was a major humiliation for Perez that came after the shadiest attempt to usurp soccer’s structures.

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27. Bill Belichick

A serial winner with the New England Patriots, Belichick is also a master of the dark arts. His teams were embroiled in numerous scandals over the years. Meanwhile, Belichick was also in the middle of them. The most notorious was in 2007 after the SpyGate saga. The Patriots lost a first-round pick while Belichick received a $500,000 fine. This was because the Patriots secretly videotaped the Jets’ sideline during a game.

Of course, this was an illegal thing to put in place. Nor was it the first time that Belichick encouraged this practice. Then there was the DeflateGate scandal. But Belichick threw Tom Brady under the bus for that one. As a result, Belichick’s reputation is one of the shadiest in the sport. Opponents accused his teams of bugging their locker room and interfering with their radio waves.

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26. Bobby Petrino

First off, Petrino was a good collegiate football coach. There was no denying his effectiveness and that’s why schools continue to hire him. But he’s also one of football’s shadiest individuals. Petrino always has one foot out of the door. This is because he doesn’t want to go down with a sinking ship. The Atlanta Falcons found this out when he abandoned overnight.

Petrino quit the 3-10 Falcons for Arkansas without telling any of his players. Nobody could believe the way he ran away from the franchise. Meanwhile, he lost his job after an affair with a female employee. This emerged after he crashed his motorbike while she was a passenger. However, he still finds work despite his character flaws. In the end, it’s on-field results that matter.

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25. Silvio Berlusconi

A four-time Prime Minister of Italy, Berlusconi is the former owner of AC Milan. He oversaw the club for 20 years winning many trophies. However, his antics away from soccer ran the club into the ground. This was because he became embroiled in over 20 court cases before 2009. This was a major turning point for Milan because they could no longer afford to buy the best players.

Definitely one of the sports’ shadiest figures, Berlusconi is a dubious character. Berlusconi was convicted of tax fraud. He also faces many other charges like sexual relations with a minor. Meanwhile, he can’t shake allegations of mafia links. Berlusconi is colorful and sleazy in equal measure. Worth billions of dollars, he invites controversy wherever he goes. Behind his smiling facade, he’s ruthless.

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24. Howard Schultz

When Schultz became a leading shareholder of the Seattle Supersonics, fans were ecstatic. The CEO of Starbucks was one of the city’s most successful businessmen. As a result, fans flocked to the chain’s coffee shops in support. However, Schultz is a New York native and not a sentimental figure. That’s why he had no problem tearing the SuperSonics out of Seattle.

This irreparably damaged his image in Seattle. The only saving grace was that their name and color scheme were left behind. Schultz was a driving force behind the franchise’s move to Oklahoma City. On the face of it, this was a strange move because Seattle is a bigger market. He revealed his regret about the situation 10 years later. But that was too little, too late.

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23. Robert Irsay

We’ve tried to keep this list of people who are alive. However, Irsay made this impossible. He packed up the Baltimore Colts overnight and drove the franchise to Indianapolis. A fleet of moving vans took them to Indiana in the dead of night before fans knew their team was gone. It remains one of the most devious moves in the history of the NFL.

This came after relationships with coaches and players imploded at various points. Irsay is definitely not a popular name in Maryland now because he ripped the heart of the community. Many of their former fans say that Indianapolis feels like a totally different franchise. The audacity of his decision is almost glorious but is definitely one of the shadiest moves ever.

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22. Ben Johnson

Johnson went from hero to villain overnight in Canada. He became an icon after winning gold in Seoul in 1987. Unfortunately, it was too good to be true. The sprinter failed drug tests after the race and lost his medals as a result. A glance at his bulging physique before showed veins popping out of him – it would have been crazier if he wasn’t on steroids.

Crazily, Johnson failed several more drug tests after this. He attempted numerous comebacks but never stayed clean. After his third failure, a Sports Minister branded him a national disgrace. It’s safe to say that he lost all credibility because of this. Few people had any respect for him because he was a blatant cheater. The reason he’s not further up this list of shadiest sportspeople is that he was too dumb.

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21. Barry Bonds

In 2007, Bonds broke Hank Aarons’s hallowed 33-year home run record. Everybody knew he was going to do it but Commissioner Bud Selig didn’t even attend the game. This was because of Bonds’ reputation as one of MLB’s shadiest players. He was the main beneficiary of the Steroid Era. Bonds broke record after record while allegedly taking amphetamines throughout his career.

Of course, he wasn’t the only one. The likes of Roger Clemens, Alex Rodriguez, and many others failed drug tests before and after Bonds played. But Bonds was blatant in his cheating. A normal human couldn’t achieve what he did. In the end, MLB changed the rules. Meanwhile, Cooperstown banned him from the Hall of Fame. However, he still made millions of dollars from cheating.

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20. John Calipari

Calipari is like a cockroach. Numerous scandals arose over the years with his name linked yet he survives everything. It’s almost admirable how effective he is at keeping his nose clean. His most dramatic story was when Memphis tapped up Derrick Rose. They cheated his SAT results so that he could win a scholarship to the school.

An NCAA investigation revealed the truth but it also failed to incriminate Calipari in the process. Then there was the Marcus Camby ‘grocery money’ incident. While at UMass, Calipari allegedly allowed NBA agents to tap up Camby. Once again the NCAA cleared his name of any wrongdoing. Since settling down in Kentucky, Calipari has stayed very clean.

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19. Andrea Agnelli

Agnelli is one of those sports executives who thinks he’s smart because he has a lot of money. However, the truth is that he inherited a massive fortune from his family. He took over Juventus after the infamous match-fixing scandal and revitalized the club’s fortunes. But Agnelli is not a hero. In fact, he is one of European soccer’s shadiest and greediest.

Firstly, he was the subject of an investigation in 2014, after allegations of mafia infiltration into his team. He received a one-year ban from football for his illegal ticket sales. Then, in 2021, he attempted to lead Juventus into a European Super League. This was a total failure. But it was an attempt to violate the conventions of European soccer. He also revealed his greed in the process.

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18. Gary Bettman

Bettman is the first of several Major League commissioners on this list. He is arguably the least successful of any of them even though hockey is arguably the most exciting sport. It is so fast-paced and has incredible action but Bettman’s reign has seen viewing numbers decline in key areas. He focused on the Sun Belt because of the lucrative revenues there than in loyal hockey markets.

Meanwhile, he oversaw three lockouts. One of these resulted in the write-off of an entire season. In short, this was an absolute disaster. As a result, many hockey fans loathe him. Like all of the shadiest sporting figures, money is everything to Bettman. It’s not about delivering a great product but gaining a major profit. But this is short-term thinking.

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17. Bob Baffert

The most famous racehorse trainer in the United States, Baffert has had extreme success. His stables have seven Kentucky Derby victories to their name. But not everything is as it seems with this shadiest of characters. His horses failed 31 drug tests over the course of 40 years. In sum, that’s an average of one per year. Somehow he maintained credibility until 2021.

Then his horse Medina Spirit failed a drug test after its Kentucky Derby win. This led to other races suspending Baffert’s horses. Furthermore, he attracted the ire of Former President Donald Trump. Trump sneered at Baffert’s misfortune and labeled the horse a junkie. To be fair, he wasn’t far wrong. Baffert tried to say a groom urinated on the horse’s hay after consuming cough syrup. Right.

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16. Chatri Sityodtong

ONE labels itself as Asia’s biggest sports holding company. They also consider themselves the region’s equivalent of the UFC. Led by Sityodtong, the promotion is active across the continent and boasts millions of potential viewers worldwide. However, this promotion has a dark side. Firstly, Sityodtong has direct links to Evolve MMA in Singapore. Many fighters from this gym receive favorable match-ups and treatment.

Another problem is that other fighters endure punishments if they beat one of his favorites. For example, they may go unbooked for the near future and left stuck in a contract. Furthermore, the promotion has a dubious weight-cutting record and has no known anti-doping policies. If a result doesn’t go Sityodtong’s way, he’ll even call fights a no-contest and create a rematch. He talks a good game but he’s one of MMA’s shadiest promoters.

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15. Roger Goodell

NFL owners love their league’s commissioner because he’s on their side. The 2011 NFL lockout was a joke but he got it sorted out in the end. Meanwhile, his solution to the 2012 referee lockout was crazy. The league brought in a host of college referees who weren’t up to the job. It was a disaster from beginning to end. However, Goodell stood by his decision. He was the only one who thought it was a good idea.

Meanwhile, Goodell personally decides punishments for teams that break rules. He has far too much power for one man and uses it freely. One of his shadiest actions was his attempt to cap concussion compensation. As the NFL lawsuit rumbles on, he’s getting nervous. These high-ranking major league officials don’t care about player welfare. Overall, they’re only interested in making money.

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14. Stan Kroenke

Kroenke is the owner of one of the most notorious sports holding companies in the world. His business owns almost every franchise in Colorado. Meanwhile, their flagship brands are Arsenal FC and the L.A Rams. It’s these two teams that make him one of the sporting business’s shadiest figures. St. Louis fans loathe him because he moved their franchise to California. The city felt betrayed by his greed and decision.

Meanwhile, in 2021, he attempted to lead Arsenal out of the Premier League. The new European Super League crashed and burned in three days. But Kroenke stained his reputation even further. However, Kroenke genuinely doesn’t care what fans think about him. He’s not interested in success on the field. It’s all about making money for him. That’s why his business is successful but his teams are not.

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13. Ali Abdelaziz

One of MMA’s most famous managers, Abdelaziz is very successful. The Afghan is the founder of Dominance MMA and represents many champions. His decorated stable include the likes of Khabib Nurmagamedov, Kamaru Usman, and Henry Cejudo. While Abdelaziz’s personal success is remarkable, he’s also one of MMA’s shadiest figures. First of all, he maintains a relationship with Chechen dictator Ramzan Kadyrov.

Kadyrov’s regime is one of the most brutal in Europe. Meanwhile, in MMA, Abdelaziz has become involved in violent scuffles. He allegedly punched his fellow manager, Malki Kawa, and put a pregnant woman in danger. Furthermore, he uses his fighters to enhance his own fame. It’s cringeworthy because he often speaks for them and tweets from their accounts. But overall, there is just no doubting his effectiveness as a manager.

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12. Eddie Hearn

As one of boxing’s most visible promoters, Hearn is incredibly successful. He is one of the faces of British boxing and represents the likes of Anthony Joshua and Tony Bellew. Furthermore, he worked with Canelo Alvarez in 2021. Barry Hearn founded the Matchroom promotion and passed it down to his son. However, it’s impossible to work in the world of boxing without being involved along some of the sports’ shadiest figures.

While Hearn avoids personal controversy, he isn’t afraid of working with those standing knee-deep in it. He has relationships with cartel boss Daniel Kinahan and MTK. Meanwhile, he has led boxing to Saudi Arabia where Crown Prince Muhammad Bin Salman throws money at the sport. This is because Bin Salman wants to sports-wash his country so people ignore their horrendous human rights record.

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11. John Terry

Former Chelsea captain Terry became one of the most notorious players in the sport. One of his earlier and shadiest actions was his illegal tours of Stamford Bridge stadium. Terry earned well over $150,000 per week but still took cash to show people around the facilities. It was ludicrously petty and he received a fine for his actions. However, Terry proved that he was capable of even sleazier behavior.

Terry became embroiled in a massive scandal when it emerged that he had an affair with the ex-girlfriend of a former teammate. He began seeing Vanessa Perroncel while he was married. He was also a teammate of Wayne Bridge, Perroncel’s former partner. Then, there was the racism scandal, when he verbally abused Anton Ferdinand on the field. In sum, Terry is a piece of work.

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10. Greg Williams

Williams is one of the shadiest figures in the NFL. ‘Bountygate’ was a major scandal after it emerged that Williams rewarded players for injuring opponents. This occurred during his time as defensive coordinator in New Orleans. The NFL found out and suspended him indefinitely for his actions. Of course, he returned after just a year on the sidelines. It was heavily evil.

Allegedly, Williams ran similar schemes during his tenures in Washington and Buffalo. Both franchises denied this but the allegations haven’t gone away. Nor is it likely that Williams just came up with the idea during his time at his sixth franchise. Furthermore, he never coached a game for the Rams because of his NFL punishment. This was definitely one of the craziest stories in recent NFL history.

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9. Joshua Fabia

Fabia entered the MMA world in 2019 when he became Diego Sanchez’s coach, manager, and life mentor. Leader of the School of Self-Awareness, Fabia soon attracted criticism from media, fans, and UFC fighters. Everybody saw him as a snake oil salesman and accused him of taking advantage of Sanchez. Former UFC athletes Matt Serra and Paul Felder shredded him in verbal confrontations.

His relationship with Sanchez reached its disturbing zenith in 2021. Video footage revealed Fabia kicking and punching Sanchez as the fighter hung upside down from a beam like a punchbag. Meanwhile, he also cost Sanchez his job in the UFC after accusing the promotion of not caring about his welfare. Fabia is one of the strangest and shadiest personalities in the MMA world. He’s also ironically, quite devoid of the self-awareneww he claims to run a school of.

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8. Lane Kiffin

A long-serving college football coach, Kiffin only spent a season with the Tennesse Volunteers. However, that was long enough to assert himself as one of the shadiest figures in the game. Everywhere he goes he gets involved in some kind of unsavory incident. But his tenure in Tenessee brought this to the next level. For example, he used interns to contact high schools and try to influence their players.

Then there were the deflategate scandals and the jersey-switching incidents. Kiffin is a cowboy but he still attracts big-name schools. A student manager paid the price for the first incident, but everybody knows that Kiffin had a hand in it. College football is a ruthless game because executives and coaches exploit their athletes. Remember, while they receive benefits they don’t make money. Coaches such as Kiffin are constantly hustling.

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7. Joel Glazer

Fans of the Tampa Bay Buccanneers love the Glazers now after they won the Super Bowl in 2021. However, the family maintains a very different relationship with their soccer team, Manchester United. They faced accusations of asset-stripping and allowing the club to decline. In 2021, they even tried to take the club out of the Premier League to join the new European Super League.

Hundreds of fans invaded the stadium field to show their anger and the Glazers backed down. Meanwhile, Old Trafford Stadium is rusting away and the team is failing to win trophies. The loss of head coach Sir Alex Ferguson in 2012 coincided with the team’s lack of competitiveness. Fans believe that they are pouring their attention into Tampa while allowing United to suffer.

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6. Lance Armstrong

Armstrong put cycling on the map but also ruined the sport’s reputation. The American star won the Tour de France an incredible seven consecutive times. This included a victory after he recovered from cancer. However, World Cycling stripped him of all his accolades after one of the most shocking doping scandals ever. This was systemic cheating at the highest level and Armstrong was in the middle of it.

It wasn’t even a case of Armstrong cheating by himself. A court proved that he bullied teammates into using PEDs as well. In the end, he confessed to cheating and lost out on over $150 million. Furthermore, his reputation as one of the sports’ shadiest figures was embedded in stone. This scandal transcended cycling because he was a global figure. In the end, he became a figure of embarrassment.

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5. Daniel Kinahan

Irish courts named Kinahan as the leader of one of Europe’s most violent drug cartels. Responsible for almost 20 murders in Ireland and Spain, they a brutal force. Currently, Kinahan lives in exile in the Middle East, where he avoids extradition. Why does this matter? He is also a major influence in boxing because of his promotion, MTK. MTK insists that Kinahan is no longer affiliated with them But everybody knows the truth.

In 2020, heavyweight champion Tyson Fury made waves when he thanked Kinahan on Twitter. It was seen as an attempt to legitimize Kinahan and sports-wash his reputation. Kinahan maintains an advisory role with many fighters like Fury and Billy Joe Saunders. Meanwhile, his cartel allegedly deals drugs, launder money, and ruins the lives of innocent people. He’s definitely one of boxing’s shadiest figures.

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4. Rob Manfred

MLB commissioners are typically some of the worst in American sports. Bud Selig was dreadful but Manfred makes his predecessor look competent. Franchise owners love Manfred because he is their man. They are making more money than ever before but at the expense of baseball. Meanwhile, players and fans loathe him because he does very little to improve their experience. He’s been awful from beginning to end.

Firstly, his mealy-mouthed reaction to the Houston Astros’ sign-stealing scandal was ludicrous. His justification for failing to strip them of their 2017 title win was that nobody had done it before. Then, he came into conflict with players after attempting to force them to take pay cuts and risk their health in 2021. Needless to say, this went down like a sack of potatoes. Overall, he’s as well-liked as a cockroach in a Big Mac.

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3. Don King

King literally killed people. This definitely makes him one of the shadiest people on this list. The boxing promoter is one of the most notorious figures in the history of the sport. He exploited fighters like boxing was going out of fashion. King’s legal team is always busy. This is because they’ve faced so many lawsuits down through the years. Larry Holmes, Lennox Lewis, and Muhammad Ali all sued the promoter.

It all comes down to money because King sneakily attempted to underpay his fighters. Mike Tyson also sued him for millions of dollars and won the case against King. He also called him ‘vile’ and ‘greedy.’ Those words adequately sum up one of the shadiest figures in sports promotion. Historically, boxing has a terrible reputation but King is one of the worst offenders. It’s amazing he’s never spent time in jail.

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2. Dan Snyder

Snyder owns the Washington Football Team and is one of the NFL’s most notorious figures. Fans and pundits alike have criticized him heavily for his actions. First and foremost, Washington has a losing record since he took charge in 1999. At the end of the day, results on the playing field affect public perception like nothing else. If they were good, then many fans would overlook his other misdemeanors.

Then there was the controversy over the ‘Redskins’ nickname. Activists and Native American support groups advocated for a change for years. Finally, Snyder dropped the ‘Redskins’ name after sponsors threatened to pull out. In short, he didn’t listen to the fans but rather the money. Meanwhile, he recently faced sexual harassment allegations. Snyder was involved in some of the league’s shadiest shenanigans.

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1. Dana White

UFC President White is one of the most visible promoters in the world of combat sports today. He is also one of the shadiest characters out there. White is a serial liar. In sum, he has made millions of dollars off the backs of his fighters. Meanwhile, he has also had a ridiculous number of fallouts with his athletes. This is because his organization underpays them. They care more about profits than fighter welfare.

Whenever a fighter demands more money, White regurgitates the same tired old lines. He almost always says that they are ‘afraid’ of their opponent. Then, he makes out that they are being unreasonable. Jon Jones, Conor McGregor, and Dustin Poirier have one thing in common. They have all had problems with the bald one in the past. but White is like a dictator in his Las Vegas castle.

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30 Shadiest Individuals In All Of Sports History

30 Shadiest Individuals In All Of Sports History

30. Robert Kraft

29. Bob Arum

28. Fiorentino Perez

27. Bill Belichick

26. Bobby Petrino

25. Silvio Berlusconi

24. Howard Schultz

23. Robert Irsay

22. Ben Johnson

21. Barry Bonds

20. John Calipari

19. Andrea Agnelli

18. Gary Bettman

17. Bob Baffert

16. Chatri Sityodtong

15. Roger Goodell

14. Stan Kroenke

13. Ali Abdelaziz

12. Eddie Hearn

11. John Terry

10. Greg Williams

9. Joshua Fabia

8. Lane Kiffin

7. Joel Glazer

6. Lance Armstrong

5. Daniel Kinahan

4. Rob Manfred

3. Don King

2. Dan Snyder

1. Dana White

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