Top 15 Greatest Cheaters in Sports

By Bob Eckstein, of The Bob

15. Hans Niemann

New to this list but with a bullet, Neimann has turned the chess world upside down, being accused of using a computer to help him cheat in hundreds of games (The super nerd’s next move was to slap grandmaster Magnus Carlsen and Chess.com, the world’s largest chess website, with $100 million defamation suit.)

Punishment: The case is still pending but there is no harsher punishment than being kicked out of the chess club.

14. Houston Astros

One of baseball’s biggest cheating scandals in years tarnished the team’s championship in 2017.

Punishment: the manager and general manager were fired, and the team was fined $5 million and docked several top draft picks. 

13. Ty Cobb

Sure, he was involved in a game-fixing scandal but that’s not why he’s on this list (and why Pete Rose isn’t included—Charlie Hustle never pulled a Buckner to throw a game. The bar is high here.) Cobb was a dirty player who spiked players in the family jewels on a regular basis. Just imagine anyone doing the same in any other sport. There is no equivalent in modern-day sports where an athlete flies into you with metal cleats.

Punishment: Legacy tarnished and universally known as a player that fans loved to hate.

12. Renee Richards

This is a stickler because on one hand an argument can be made for this transgender Hall of Famer being a brave trailblazer, but many competitors couldn’t help but notice that as a man Dr. Richards could not break into the pro tour but as a woman reached a high of #20 in the world, twice semi-finalist mixed-doubles U.S. Open with notorious cheater Ilie Nastase.

Punishment: had to endear unfair ridicule and was late-night TV fodder.

11. Rosie Ruiz

Won the 1980 Boston Marathon by taking a shortcut. In her defense, many people always preach to take public transportation. She used the subway.

Punishment: In 1982, Ruiz was arrested for embezzling $60,000 from her job and spent one week in jail, five years’ probation. Next year she was running (from the law) and was busted in a cocaine deal and sentenced to three years probation.

10. Tiger Woods

Tiger is the second greatest golfer in the world and is roundly considered with Wayne Gretzky, Roger Federer, and Michael Jordan, part of the Mount Rushmore of sports. On the course, he exhibited exemplary sportsmanship. Off the course, no athlete in history did more to damage to their career from their cheating, having won 14 of his majors before it was disclosed, he had a reported 18 mistresses (the same amount of majors Jack Nicklaus holds.)

Punishment: Tiger has won only one major since his double-bogey. Divorce settlement costs him an estimated $100-110 million.

9. Gaylord Perry

Perhaps no cheater in sports history, along with grifter/tennis player Bobby Riggs, leaned into it with such pride and humor as Perry, wearing it like a badge of honor. Perry doctored balls for eight teams from 1962 to 1983 and was the oldest Cy Young winner (40) at the time.

Punishment: was elected into the Baseball Hall of Fame in 1991.

8. Ilie Nastase

One of the most gifted and obnoxious players ever to play tennis. The former number one player in the world and International Tennis Hall of Famer holds records for suspensions, violations, and fines that even John McEnroe cannot hold a candle to.

Punishment: constantly getting into trouble on Twitter.

7. Diego Maradona

His controversial “Hand of God” goal in the 1986 World Cup was a clever maneuver, where Maradona palmed the ball. Maradona used his hand again in the 1990 World Cup, again without punishment, on his own goal line, to prevent a Russian goal.

Punishment: not much.

6. Bill Belichick

We contend Tom Brandy didn’t want to throw his coach under the bus but that the football air pressure controversy was somehow Belichick’s handiwork, too.

Punishment: the NFL fined the Patriots and Belichick multiple times. In 2008, the team was fined $250,000 and a first-round draft pick. In 2015, for Deflategate, Tom Brady was suspended for four games, the Patriots fined $1 million and the club forfeited a first- and fourth-round draft pick. In 2020, the team earned a $1.1 million fine, lost a third-round draft pick and Belichick was fined personally for $500,000 for spying on teams.

5. Ben Johnson

Poster boy for Olympic steroid use, he was once the ‘fastest man alive’ competing for Canada.

Punishment: was stripped of his gold medal and world record. A Canadian Olympic swimmer hung a bed sheet banner out his Olympic Village apartment window that said, “Hero to Zero in 9.79.”

4. Lance Armstrong

Nobody has made peeing into a cup more problematic.

Punishment: Lost many lawsuits, civil suits, sponsors, medals, and Sheryl Crow.

3. Tonya Harding

She was the first American woman to land a triple Axel and the first two-time Olympian and a two-time Skate America Champion to almost land in jail after orchestrating an attack on teammate Nancy Kerrigan.

Punishment: She was banned from skating while her husband served two years in jail. She was issued a $100,000 fine and 500 hours of community service.

2. Barry Bonds

Bonds was indicted in 2007 on charges of perjury and obstruction of justice for lying to a grand jury during a federal investigation. Bonds was convicted of obstruction of justice in 2011 but the conviction was overturned in 2015.

Punishment: In his 10 years of eligibility, despite being one of the greatest players in baseball and the only player with at least 500 home runs and 500 stolen bases, he has not yet received the 75% of the vote needed to be elected to the Hall of Fame.

1. 1919 Chicago White Sox

The award must go to the originators of the Black Sox Scandal, the first game-fixing scandal in which eight members of the White Sox were accused of throwing the World Series for money from a bookie. The scandal defines cheating and gave baseball a black eye it has actually still never recovered from.

Punishment: all eight players were permanently banned from baseball.