Sports

The 50 Biggest Sports Villains

From sports figures that used dirty tactics on the field to those who had to serve time off of it, say hello to the bad guys.

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Intro

Like any classic film, every sport has had a few villains. The type of guys who we despise but realize are completely necessary to keep things entertaining. After all, the next best thing to rooting for your favorite player or squad is rooting against the ones you loathe the most. The world of sports has a variety of these characters, though. From ballers who are known for their dirty tactics on the field (nut-grabbing and sticking your fingers up opponents asses? Really?!) to owners who ran franchises into the ground or out of town over night (literally!), here are the 50 Biggest Sports Villains of All Time...

Joe Paterno

50. Joe Paterno

Position, Team: Head Coach, Penn State
Years: 1966-2011
A month ago, Joe Paterno's rep seemed invincible. He was the winningest coach in Division I history with 409 wins and two national titles. Then earlier this month, it was revealed that in 2002 Paterno had been notified of alleged sexual child abuse by his former defensive coordinator Jerry Sandusky and reported it to school officials but failed to go to the police. Joe Pa's rep was tarnished and he was dismissed as head coach of the football program only days later. This Jigga line has never sounded so true: "Dark knight feeling, die you'll be a hero, or live long enough to see yourself become the villain."

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Jack Tatum

49. Jack Tatum

Position, Team: Safety, Oakland Raiders/Houston Oilers
Years: 1971-1980
Despite putting together a short but solid career which included three Pro Bowl selections and a Super Bowl championship, Jack Tatum will forever be remembered by his infamous hit on Darryl Stingley. The hit left Stingley paralyzed and the two never spoke again as Stingley died in 2007 and Tatum in 2010. Tatum also never apologized for the hit saying, "People are always saying, 'He didn't apologize.' I don't think I did anything wrong that I need to apologize for. It was a clean hit."

Latrell Sprewell

48. Latrell Sprewell

Position, Team: Shooting Guard, Golden State Warriors/New York Knicks/Minnesota Timberwolves
Years: 1992-2005
Ever dreamt of choking out your boss? Don't answer that. Especially if you're at work right now. Anyway, back in '97, Latrell Sprewell acted on this demented fantasy when he put his hands on the throat of Golden State Warriors head coach P. J. Carlesimo. As a result, he was suspended for the remaining 68 games of the season, the longest suspension in league history at the time. Years later, in 2005, Sprewell would catch heat from fans once again when he scoffed at a 3-year, $21 million contract offer from Minnesota claiming "I have my family to feed." Sprewell ended up not receiving a bigger contract or any contract for that matter and hasn't been in the league since. In 2008 his yacht was repossessed and his home went into foreclosure. Hmmm...should today's NBA players be taking notes? Just putting it out there...

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Clay Bennett Greg Nickles

47. Clay Bennett and Greg Nickles

Position, Team: Oklahoma City Thunder owner and Seattle Mayor
Years: 2006-present and 2002-2010
Around this time of the year, you'll hear about classic holiday tales like How The Grinch Stole Christmas. Well, this is the real-life story of how Seattle had one of their most beloved sports franchises stolen from them. A failure to get local governments to put up $500 million for a new arena and other politics resulted in the Sonics moving to Oklahoma in 2008. No knocking OKC but straight jacking a franchise from a city that needed it is not a good look. Who do people in Seattle have to root for now, the Mariners? Seachickens? FOH.

Brian Bosworth

46. Brian Bosworth

Position, Team: Linebacker, Seattle Seahawks
Years: 1987-1989
The bully steroid-using linebacker used the hype of his college career to get himself the biggest rookie contact in league history at $11 million over 10 years. Then once dude made it to the league he got exposed as one of the biggest draft busts in league history, spending only three years in the pros. The "highlight" of his career came when Bo Jackson gave him that dose of ether on MNF.


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Al Davis

45. Al Davis

Position, Team: Owner, Los Angeles/Oakland Raiders
Years: 1970-2011
Upon one's death, people usually focus on the positive things the deceased has done in their lives. And while Al Davis did have a number of gangster moves which did a lot of good for the game like being the first owner to hire a black head coach and being one of the most passionate owners in pro sports history, he's also known for a number of controversial moves, too. Such as moving the team from Oakland to L.A. and back to Oakland again then once again attempting another move to L.A. afterward. Or his public feuds with players like Marcus Allen and hiring and firings of head coaches in latter years. Near the end, Davis began to look like a crazy old man who didn't know when to relinquish power and wasn't afraid to bust out the overhead projector on you young'ns. Word to Lane Kiffin.

Leo Durocher

44. Leo Durocher

Position, Team: Shortstop/Manager, New York Yankees/Cincinnati Reds/St. Louis Cardinals/Chicago Cubs/Houston Astros/New York Giants
Years: 1925-1973
With nearly 50 years in the league combining his time as a player and manager, Leo Durocher had his fare share of career highlights including four World Series titles and three All-Star Game selections. But he's known as "Leo the Lip" for a reason. His ability to talk trash with the best of 'em led to 95 career ejections as a manager (fourth on the all-time list) and a year-long suspension for gambling players in a rigged game of craps during spring training of 1947.

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Nick Saban

43. Nick Saban

Position, Team: Head coach, Toledo/Michigan St./LSU/Miami Dolphins/Alabama
Years: 1990-present
It takes a certain type of dude to be successful and win two national championships in the crazy and shady world of college athletics. Now, what type of dude Nick Saban depends on who you ask. If it's a Dolphins fan they'll probably call him a lying and conniving son of a bitch. The way he dipped out on the team at the end of the 2007 season to join the Crimson Tide despite denying rumors for weeks was kind of grimey. Alright, it was very grimey. To the point where former Dolphins tight end Jim Mandich challenged Saban to a fight. Instead of taking part in such fuckery, Saban just went on to win another national title in 2009. #stunt101 #getoffme

Sean Avery

42. Sean Avery

Position, Team: Left wing, Detroit Red Wings/Los Angeles Kings/Dallas Stars/New York Rangers
Years: 1998-present
We'll give credit to Sean Avery for changing the game but it was for the wrong reason (see: Avery Rule). He's also known for being one of the most annoying players in league history and talking slick about other people's wifeys whom he's happened to have past relationships with. How this guy plays in the NHL yet still has a grill to show off, we have no clue.

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James Harrison

41. James Harrison

Position, Team: Linebacker, Baltimore Ravens/Pittsburgh Steelers
Years: 2002-present
Ahh the poster boy for ridiculous fines in the No Fun League. Last season, James Harrison racked up nearly $150K in fines for illegal hits. Harrison's rep isn't only limited to the field, though. A domestic violence arrest in '08 and a snub of a White House invite from president Barack Obama in 2009 garnered negative attention for the Steelers linebacker. But the biggest controversy of all came last summer in Men's Journal where Harrison said this about commissioner Roger Goodell: "If that man was on fire and I had to piss to put him out, I wouldn't do it." Well, damn. Tell us how you really feel, James.

Bud Selig

40. Bud Selig

Position, Team: MLB Commissioner
Years: 1992-present
While other people in positions of power are on this list because of their blatant abuse of it and intentionally evil ways, Bud lands on here basically for his incompetence and unwillingness to take action and improve the sport. Sure he's brought positive aspects like having Wild Card teams and introducing a bit of revenue sharing but he was also acting commissioner during the 1994 strike and looked over much evidence of steroids corrupting the game. As a result many kids have fallen victim to the hype of PEDs and have sacrificed their bodies in the process.

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A.J. Pierzynski

39. A.J. Pierzynski

Position, Team: Catcher, Minnesota Twins/San Francisco Giants/Chicago White Sox
Years: 1998-present
A.J. Pierzynski—like many people you'll see on this list—is a player you either love because he plays for your team, or hate because he's on the opposing side. He's known for lashing out against his former teams like the time he appeared to spike Justin Morneau while running inside the first base line. His don't give a fuck attitude hasn't always worked out for him, though. In 2006 Cubs catcher Michael Barrett punched A.J. in the face after a collision at the plate. If you talk tough, you gotta be prepared to do tough things.

Brock Lesnar

38. Brock Lesnar

Position, Team: WWE wrestler and UFC fighter
Years: 2002-present
Before joining UFC in 2007, Brock Lesnar developed his bad boy persona in the WWE by having feuds with everyone from the Hardy Boyz to the Undertaker. He carried this rep into the all-too-real sport of MMA at UFC 100 when he flipped off the crowd and dissed Bud Light, the sponsor of the event. He later apologized at the post-fight press conference. Uhh...yeah, that reckless shit may have worked in the fake world of WWE but not in the UFC. Dana don't play that.

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Scott Boras

37. Scott Boras

Position, Team: Sports Agent
Years: 1982-present
The man responsible for many of the largest contracts in baseball and sports history got his start in 1983 when he negotiated a record-setting deal for shortstop Bill Caudill ($7.5 million). Since then deals for players like Kevin Brown ($100 million) and Alex Rodriguez ($252 million) have made Boras ridiculously paid while damn near eliminating the competitive balance in the MLB. Without people like him, shit like this wouldn't be possible.

John Hopoate

36. John Hopoate

Position, Team: Wing, Manly-Warringah/Wests Tigers/Northern Eagles/Manly-Warringah
Years: 1993-2005
Rugby is a pretty reckless sport. That being said, all we're going to say is this guy was caught sticking his fingers up opponents butts during games. Yikes.

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Walter O'Malley

35. Walter O'Malley

Position, Team: Owner, Brooklyn/Los Angeles Dodgers
Years: 1950-1970
Many fans in BK could never forgive Walter O'Malley for moving one of New York's most storied franchises across the country. But Mexican-Americans who lived in the Chavez Ravine area were losing a lot more—their homes. Residents of the area were either offered small amounts of money or forced to move in order to make way for Dodger Stadium. The tension between the Mexican-American community and Dodger organization would last for decades. See sometimes, it's more than just a game when money and power are involved.

Alex Rodriguez

34. Alex Rodriguez

Position, Team: Third baseman, Seattle Mariners/Texas Rangers/New York Yankees
Years: 1994-present
Whether it was using steroids or joining the Evil Empire, A-Rod has been a pure opportunist throughout his career. The most prominent example of his dirty on-the-field tactics wes his epic fail of a swipe during Game 6 of the 2004 ALCS. Off the field he's even beefed with DJ and talked badly about the shortstop in an effort to bag women! SMH, soundtrack please!


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Bill Belichick

33. Bill Belichick

Position, Team: Head coach, Cleveland Browns/New York Jets/New England Patriots
Years: 1991-present
No one expects head coaches to have the personalities of players but when they appear like the heartless machine that shuffles around and calls himself Bill Belichick it starts getting ridiculous. Belichick is no stranger to beef, though. His most testy moments coming in his public feud with his former defensive coordinator turned rival Eric Mangini. Throw in that with the fact that he's won three Super Bowls courtesy of talented teams and tactics like spying on the other squad and you can see why no one really likes dude.

Tonya Harding

32. Tonya Harding

Position, Team: Figure Skater
Years: 1986-1994
Who knew a figure skater could be responsible for one of the grimiest acts in sports history? When Tonya Harding put the hit out on Nancy Kerrigan before the 1994 U.S. Figure Skating Championships she became forever infamous. Only thing more disturbing than hearing Kerrigan screaming in pain was Harding's sex tape that leaked a few years back. *shudder*

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Mike Tyson

31. Mike Tyson

Position, Team: Pro Boxer
Years: 1985-2005
Because Iron Mike has had a rebirth in recent years as a loveable and funny former athlete many people have forgotten his past reputation as the Baddest Man on the Planet. In the ring, his black trunks and string of vicious knockouts intimidated fighters throughout the mid and late '80s. Outside of the ring, domestic violence accusations, a rape conviction, and several other run-ins with the law made him arguably the most fascinating yet controversial sports figure of the last 25 years. Cap that off with the Bite Fight and his epic interviews and Iron Mike truly qualifies for a spot on this list.

Terrell Owens

30. Terrell Owens

Position, Team: Wide Receiver, San Francisco 49ers/Philadelphia Eagles/Dallas Cowboys/Buffalo Bills/Cincinnati Bengals
Years: 1996-2010
Ahh, Team Obliterator as Skip Bayless would say. A few years ago no player caused more controversy in the league than Terrell Owens. Whether it was his over-the-top TD celebrations, his knack for throwing his QBs under the bus, or just his love of the spotlight, T.O. made headlines (most of 'em negative) nearly every week. He'd rank higher but his image as a villain has gone down a bit in recent years as he's struggling to get back into the league and is facing financial troubles.


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John Rocker

29. John Rocker

Position, Team: Pitcher, Atlanta Braves/Cleveland Indians/Texas Rangers/Tampa Bay Devil Rays
Years: 1998-2003
Want to find a quick way to get eight million people to hate you? Do an interview with SI and say stuff like this about the nation's most populous city: " [Before moving there] I'd retire first. It's the most hectic, nerve-racking city. Imagine having to take the 7 Train to the ballpark looking like you're riding through Beirut next to some kid with purple hair, next to some queer with AIDS, right next to some dude who just got out of jail for the fourth time, right next to some 20-year-old mom with four kids. It's depressing..." Whoa. Imagine if this dude had a Twitter account back in the day?

Robert Irsay

28. Robert Irsay

Position, Team: Owner, Baltimore/Indianapolis Colts
Years: 1974-1996
When will owners ever learn?! Moving a storied sports franchise out of a major city and into another will make you a marked man. Especially if you do that shit overnight. Literally. Low attendance, a failed promise of a new stadium, and fear of the city immediately taking over the team are said to be the reasons behind Irsay's hasty decision on March 29, 1984. In the wee hours, Irsay cut a deal with the mayor and city of Indianapolis then brought in 15 trucks and moved the team to Indianapolis in a matter of hours. The next day riots ensued and Irsay was forced to sacrifice his first-born child. We kid but with reckless actions like his does it really seem that far-fetched?

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Vinnie Jones

27. Vinnie Jones

Position, Team: Midfielder, Wales
Years: 1984-1999
Today Vinnie Jones is more known for his acting more than anything else but back in the day he was known for making action movies on the pitch. He received 12 red cards during his career, including the fastest booking in football history, when he was sent off only three seconds into a match. Jones also had his share of somewhat pause-worthy moments during his career, starring in a video called Soccer's Hard Men and grabbing Paul Gascoigne's balls in order to "faze" him. Where they do that at?

Marty McSorley

26. Marty McSorley

Position, Team: Right Wing, Pittsburgh Penguins/Edmonton Oilers/Los Angeles Kings/New York Rangers/San Jose Sharks/Boston Bruins
Years: 1982-2001
With over 3,000 career penalty minutes, McSorley had already established himself as one of the NHL's most brutal enforcers when his vicious hit on Donald Brashear became one of the most shocking moments in sports history. The attack resulted in an assault conviction and a one-year suspension (longest in league history); McSorley never returned to the league. Brashear suffered a Grade 3 concussion, but returned to play later that season. The head game was truly vicious...ayo!

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Christian Laettner

25. Christian Laettner

Position, Team: Power Forward, Duke/Minnesota Timberwolves/Atlanta Hawks/Detroit Pistons/Dallas Mavericks/Washington Wizards/Miami Heat
Years: 1989-2005
Like most people we hate a lot of Duke players, particularly a few...uh, paler ones. But no player is more despised than Christian Laettner. He epitomized everything that was the privileged, arrogant, and devious aura that surrounds Duke. Some of the moments that make us hate him the most include him stomping on Kentucky's Aminu Timberlake during the 1992 NCAA Regional Final, the fact that he made the 1992 Dream Team when players like Shaq were left off, and he was able to have a 13-year career in the league despite being a scrub. Yeah, homie definitely brings out the Jalen Rose in us.

Todd Bertuzzi

24. Todd Bertuzzi

Position, Team: Left wing, Detroit Red Wings/New York Islanders/Vancouver Canucks/Florida Panthers/Anaheim Ducks Calgary Flames
Years: 1995-present
In one of the ugliest moments in sports history, Todd Bertuzzi became infamous when he rabbit punched Steve Moore essentially ending his career in the process. Bertuzzi received a 17-month suspension and was served with assault charges for the hit. Hockey is known for being gully and all but even the most intense puck heads saw this action as being way over the line.

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Lawrence Taylor

23. Lawrence Taylor

Position, Team: Linebacker, New York Giants
Years: 1981-1993
The O.G. LT ended Joe Theismann's career, is pretty open about his past drug use, and used the "I don't card 'em" defense after hooking up with a 16-year-old prostitute. Yeah, need we say more?


Marge Schott

22. Marge Schott

Position, Team: President, Cincinnati Reds
Years: 1985-1999
Baseball has a well-documented history of racism. But few, if any, were as blatant with their bigotry in the modern era as Marge Schott. She made comments about Japanese people, followers of the Jewish faith, and even called former Reds' outfielder Eric Davis "one of her million-dollar niggers." SMH, money doesn't by class or intelligence, folks.

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Kyle Busch

21. Kyle Busch

Position, Team: NASCAR Driver
Years: 2004-present
You know those assholes on the road that push you to the brink of catching an assault charge by doing recklessness behind the wheel? Well, Kyle Busch is that dude. Except he does those things while driving at nearly 200 mph and he's pretty damn skilled at handling the wheel, too.

Floyd Mayweather Jr.

20. Floyd Mayweather Jr.

Position, Team: Boxer
Years: 1996-present
One rule in the Sports Villains handbook (yeah, we made that up), is if you're good at what you do make sure everyone knows about it. No one really does that as well as Floyd "Money" Mayweather. Whether he's talking trash, delivering "cheap shots" (is that even possible in a boxing ring?), or getting gully with an 80-year-old analyst Pretty Boy Floyd has given haters many reasons to loathe him even more in recent years.

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Bruce Bowen

19. Bruce Bowen

Position, Team: Small Forward, Miami Heat/Boston Celtics/Philadelphia 76ers/San Antonio Spurs
Years: 1997-2009
When you think of the Spurs' championship teams from the mid 2000s, a pack of villains isn't the first description that comes to mind. One fiesty, low-blow throwing, face-kicking little man was all it took for those teams to become one of the most hated in NBA history. Don't let the bowties and Kool-Aid smile on ESPN fool you, he was definitely one of the dirtiest players in NBA history. We got dirt on you, doggy!


Roger Clemens

18. Roger Clemens

Position, Team: Pitcher, Boston Red Sox/Toronto Blue Jays/New York Yankees/Houston Astros
Years: 1984-2007
Those who liked Roger Clemens during his career called him a gritty hard-throwing pitcher who was kind of old-school because he wasn't afraid to confront batters. Well, that's kind of true if by confront you mean throwing a broken bat at hitters and beaning them in the head with fastballs. Years later we'd find out that this aggression from the six-time Cy Young winner could've come from his alleged roid usage. Figures.

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Reggie Miller

17. Reggie Miller

Position, Team: Shooting Guard, Indiana Pacers
Years: 1987-2005
If we ever do a list of the most-hated people in New York sports history Reggie Miller will definitely be Top 5. Reggie not only broke the hearts of Knicks fans in the '94 and '95 postseason, but relished in seeing New York fans in such anguish. A 39-point performance (25 of which came in the fourth quarter) of Game 5 of the '94 Eastern Conference Finals followed up by eight points being scored in the final 8.9 seconds the following year in the EC semifinals solidified his place in NBA history. Decades later, he's known for his somewhat x-rated commentary, pouring Grey Goose down broads throats, and having a song dedicated to him by Based God. Good for you, Reggie. Good for you.


Karl Malone

16. Karl Malone

Position, Team: Power Forward, Utah Jazz/Los Angeles Lakers
Years: 1985-2004
Karl Malone may have played in the very Mormon town of Salt Lake City but his play was still dirty as shit. Word to Isiah Thomas. But it wasn't just the reckless elbows and brutality in the paint that made fans dislike, Karl. It was his personality, too. Never one to shy away from voicing his opinion Karl made headlines for stating he thought Magic Johnson should be kept out of the league for fear that he may infect other players after his HIV announcement and he donated thousands to George W. Bush's reelection campaign in 2004. Funny because somehow we think those conservative views probably go against him knocking up a 13-year-old when he was a sophomore in college. Yup, that's that shit that makes your soul burn slow.

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Tie Domi

15. Tie Domi

Position, Team: Right Wing, Toronto Maple Leafs/New York Rangers/Winnipeg Jets
Years: 1989-2006
If a list of the most vicious enforcers in NHL history is ever done, Tie Domi will definitely have to be on the short end of it. Sucker-punching opponents (what up, Ulf Samuelsson?), antagonizing fans, and throwing elbows that left players unconscious are just a few highlights on his bad guy resume. Sidebar: If this were the NBA of NFL dude would've had a lifetime ban after the first couple incidents. And this is why the NHL remains the most badass major pro sport of 'em all.

LeBron James

14. LeBron James

Position, Team: Small Forward, Cleveland Cavaliers/Miami Heat
Years: 2003-present
LBJ deserves a spot in the Guinness Book of World Records for the fastest transformation from hero to villain in sports history. In a matter of 90 minutes, Bron Bron went from one of the leagues most loved to most loathed on the ESPN The Decision debacle. The shameless display of self-absorption left Cleveland fans and everyone outside of Miami wishing bad on the new King of South Beach. That was not the first or last fail for James, though. If there's anyone benefiting from the lockout just slightly we'd have to say it's this dude. #timehealsallwounds

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Pete Rose

13. Pete Rose

Position, Team: Various/Manager, Philadelphia Phillies/Montreal Expos/Cincinnati Reds
Years: 1963-1989
Everyone already knows about Rose being banned for betting on baseball, but dude was grimey way before then. A perfect example was at the 1970 All-Star Game, when he rounded third and barreled into catcher Ray Fosse, who didn't even have the ball. Fosse suffered a separated shoulder and was never quite the same. Think Fosse cracks a smile each year Rose is ineligible for the Hall of Fame? Bet!

Kobe Bryant

12. Kobe Bryant

Position, Team: Shooting Guard, Los Angeles Lakers
Years: 1996-present
Kobe isn't the type to openly play dirty or give off vibes that he wants to destroy the opposition and all their supporters. Well, sometimes. But the fact that he does this on the low and get calls from refs is what makes many fans hate him even more. Sneaky dirty plays, being responsible for the break-up of Shaq-Kobe dynasty, a rape accusation in 2003, and the fact that he could possibly go down as the GOAT have all added fuel to the fire that surrounds the Black Mamba. B.J. said it best.

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Michael Vick

11. Michael Vick

Position, Team: Quarterback, Atlanta Falcons/Philadelphia Eagles
Years: 2001-present
It wasn't just the dog fighting case of '07 that landed Mike Vick a spot on this list. His days of being an athlete fans loved to hate started a few years before then. Previous controversial incidents like flipping fans off, trying to sneak weed through an airport, and allegedly giving a young woman herpes but going under the alias "Ron Mexico" during the trial all tarnished his rep a bit before the dog fighting case kind of gave it the death blow. Or so we thought. His nine-figure contract signed this year gives people a few million more reasons to hate Vick. #momoneymoproblems?

Ty Cobb

10. Ty Cobb

Position, Team: Outfielder, Detroit Tigers/Philadelphia Athletics
Years: 1905-1928
Many say Ty Cobb was one of the biggest racists in sports history. Not true. Homie hated everyone. Teammates, reporters, opponents anyone could get it. One of his most-well known tactics was using his sharpened spikes to take out basemen. So, was he a racist? No. Was he an asshole? Yes.

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Bill Laimbeer

9. Bill Laimbeer

Position, Team: Center, Cleveland Cavaliers/Detroit Pistons
Years: 1980-1993
Bill Laimbeer personified the epitome of the Pistons' "Bad Boys" squad of the 1980s. Unless you were a fan in the Detroit-area, you most likely loathed Laimbeer for his flailing elbows, aggressiveness in the lane, and notorious flopping. Yup, he was definitely the shadiest of the Bad Boys crew...well, up until Isiah Thomas' reputation for fuckery came to light several years later.

Art Modell

8. Art Modell

Position, Team: Owner, Cleveland Browns/Baltimore Ravens
Years: 1961-2004
Want to know the most-hated man in Cleveland before LeBron James made his decision? You're looking at him, fam. It took Modell only two years to get rid of coach Paul Brown who was the most successful coach in team history having won seven league championships. It took him another three decades to run the franchise into the ground and out of Cleveland all together.

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Bill Romanowski

7. Bill Romanowski

Position, Team: Linebacker, San Francisco 49ers/Philadelphia Eagles/Denver Broncos/Oakland Raiders
Years: 1988-2003
Kicking opponents in the head while they're down? Check. Spitting in the face of others? Yup. Breaking the eye socket and essentially ending the career of your own teammate? Uh-huh. Yeah, we're probably going to need a league investigation into how a psychopath made it into the NFL.

Roy Keane

6. Roy Keane

Position, Team: Midfielder, Cobh Ramblers/Nottingham Forest/Manchester United/Celtic
Years: 1989-2006
One stat says it all for Roy Keane. He holds the record for most red cards in Premier League play (13). Now top that off with the fact that he received those while playing for Man. U. and you figure he probably deserved two or three times that amount. #keepit100

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The Yankees (circa Steinbrenner era)

5. The New York Yankees

Position, Team: New York Yankees
Years: Late '90s-present
Having the highest payroll in baseball every year since 1999 and buying, uh, we mean "winning" a few championships in the process is naturally going to make opposing fans a wee bit angry. Top that off with the fact that their fans feel entitled to a championship every year and anything less calls for splurging in the offseason along with firings then you have an idea of why the Yankees are one of the most hated teams in sports history. Evil Empire, indeed.

Don King

4. Don King

Position, Team: Boxing Promoter
Years: 1974-present
So, we already told you about how so many pro boxing champs end up going broke after making millions throughout their careers, right? Well, the man in the photo above and people like him are a big reason why that happens so often. Don King's name is straight-up synonymous with shady promoter at this point. We'd call him a bunch of other things but we think Iron Mike sums it up quite well. Oh yea, did we forget to mention he has killed two men on two different occasions? But got off easy both times, once for justifiable homicide and the other for non-negligent manslaughter? SMH, you can't make this shit up.

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Conrad Dobler

3. Conrad Dobler

Position, Team: Offensive Guard, St. Louis Cardinals/New Orleans Saints/Buffalo Bills
Years: 1972-1981
What really can be said about a dude who punched Mean Joe Green? Oh yeah, he spat on an injured Bill Bradley of the Eagles while he was sprawled out on the ground and kicked Merlin Olsen of the Rams in the head. Really, though?

Barry Bonds

2. Barry Bonds

Position, Team: Leftfielder, Pittsburgh Pirates/San Francisco Giants
Years: 1986-2007
Barry didn't end up on this list for his 'roid use alone. If that were the case you'd see Sammy "Casper The Ghost" Sosa and Mark "My Neck's Bigger Than Your Thigh" McGwire right alongside dude. It's just the arrogance and fuck you (you meaning the media and anyone who wasn't a Bonds fan) attitude that he maintained throughout his 21-year career and especially during his passing of Hank Aaron's home run record. You blame him, though? You'd be pissed too if small balls were a direct consequence of your success.

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Donald Sterling

1. Donald Sterling

Position, Team: Owner, Los Angeles Clippers
Years: 1981-present
Donald Sterling is a perfect example of how anyone with millions to spend—no matter how evil, racist or incompetent they seem—can own a sports team. Sterling's on the court fails like drafting busts like Michael Olowokandi and Benoit Benjamin have caused the team to winning percentage of .342 during his tenure. But his off-the-court transgressions are much worse. He's been accused of sexual harassment, racism, and refusing to pay the medical bills of employees diagnosed with cancer. There's bad owners and sports villains and then there's Donald Sterling.


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