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The 10 Most Horrible Bosses of the Sports World

Donald Sterling Los Angeles Clippers
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We've all had some horrible bosses, but when it comes to sports, the massive amounts of money and absolute power magnify that ten times over. Whether it's poor team management or just being an outright bad person, these bosses have found a way to make everything they've touched that much worse.

10. Gregg Williams

Gregg Williams Bountygate
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10. Gregg Williams

Gregg Williams Bountygate

Williams is the only person on this list who has only been a coach at the pro level, but running the New Orleans Saints defense through the “Bountygate” scandal certainly deserves this kind of recognition. Vikings fans everywhere still haven’t forgotten the 2009 NFC Championship game, and Williams’ reputation has been forever tarnished.

9. Marge Schott

Marge Schott
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9. Marge Schott

Marge Schott

Schott, who ran the Cincinnati Reds for 15 years, was a fan favorite for keeping ticket and concession prices down and being publicly accessible at games. Then again, there’s only so far cheap beer and hot dogs go when your racist and homophobic comments and team policies draw the ire of players, fans and fellow owners, and a single World Series ring in 1990 wasn’t enough to keep her running the team.

8. Isiah Thomas

Isiah Thomas
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8. Isiah Thomas

Isiah Thomas

Thomas was a legendary player at Indiana University and with the “Bad Boy” Detroit Pistons, but his record as a coach and executive leaves something to be desired. Presiding over the CBA as it went bankrupt, and a run with the Knicks that included blowing money on mediocre talent, missing the playoffs and a sexual harassment lawsuit, Thomas has become front office poison.

7. James Dolan

James Dolan
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7. James Dolan

James Dolan

Thomas must have learned it somewhere - James Dolan isn’t just a horrible sports boss, he’s also got the National Labor Relations Board investigating how he runs CableVision, the parent company of Madison Square Garden, the New York Knicks and the New York Rangers. Dolan doesn’t mind spending money on his Knicks, but they are consistent underperformers, proving that not everybody can buy championships.

6. Jerry Jones

Jerry Jones
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6. Jerry Jones

Jerry Jones

Jerry Jones makes a ton of money for himself and the other 31 owners, which is a big part of his job. But when Jones the Dallas Cowboys owner says he’d have fired Jones the Cowboys’ general manager if they weren’t the same person, that might be a problem. With only one playoff win since 1996, the dominant “America’s Team” of the 1990’s is little more than a distant memory.

5. Al Davis

Al Davis
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5. Al Davis

Al Davis

Al Davis gets a worse rap than he deserves as an executive, having been a forward-thinking owner and the architect of the dominant Raiders teams of the 1970s. However, he also reigned over one of the most dysfunctional franchises in all of sports before his death in 2011. Names like JaMarcus Russell and Lane Kiffin won’t be forgotten until the Raiders “Just Win” again, baby.

4. Daniel Snyder

Daniel Snyder Washington Redskins
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4. Daniel Snyder

Daniel Snyder Washington Redskins

Daniel Snyder isn't just a horrible boss, but an unrepentant one. Not only has his team been wildly underachieving for most of his 15 years as owner, but he's got a public relations nightmare on his hands, as he refuses to even acknowledge the possibility of changing the team's controversial nickname. Time to get your head out of the sand, Mr. Snyder.

3. Gary Bettman

Gary Bettman
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3. Gary Bettman

Gary Bettman

Three lockouts in the last 20 years, the loss of the entire 2004-05 season, and relocating several teams to “non-traditional” hockey markets have made Bettman one of the least popular commissioners in all of sports. Hockey in America may be getting stronger in recent years, but you almost have to wonder if that’s in spite of Bettman, not because of him.

2. Roger Goodell

Roger Goodell
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2. Roger Goodell

Roger Goodell

His “new sheriff in town” act has worn thin, and while his employers (the 32 NFL owners) are making record profits, he’s lost basically every bit of goodwill he ever had with players and fans. Botching the Ray Rice and Adrian Peterson situations is just the most recent failure on the commissioner’s part. Football is still No. 1, but Goodell is clearly on the way down, and should be gone before long.

1. Donald Sterling

Donald Sterling V. Stiviano
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1. Donald Sterling

Donald Sterling

Our worst sports boss is more than that -- he's a legitimately bad person. When he wasn’t signing off on discriminatory housing practices or allegedly sexually harassing employees, Donald Sterling found time to manage one of the least-relevant teams in the NBA. Some unsurprisingly racist remarks ended his ownership, ironically at a time when the on-court product was the best it had been from the day he took over.