11 Baseball Legends Who Were Legendary Assholes

Baseball is as synonymous with America as mom, apple pie, and morbid obesity, which probably goes hand in hand with the apple pie. We've all heard the names Ruth, DiMaggio, Aaron, these are the legends of the game who inspire us with awe and wonder.

However, with any group there's sure to be a certain number of assholes, and baseball is no different. Maybe a little worse, in fact.

#11. Jose Canseco:

First known as one of the great power hitters of the 80s and 90s, there are some who now call Jose Canseco the "Woodward and Bernstein" of the Steroids Scandal because of his tell-all book Juiced. While he did shed some light on an important issue, there is one distinct difference: Woody and the B-Dog wrote their book because they wanted to bring a corrupt President to justice because they were great journalists. Canseco wanted to make some money ratting out his old buddies because he's a douche.

If, for even a moment, you held on to a shred of possibility it wasn't all about the money, that was blown out of the water when he decided to write a second book which "had stuff" on the likes of A-Rod and Junior Griffey, two players who have never shown up in any steroids investigation. This means one of two things: Canseco was making shit up because he's a dick, or he willingly held out the most surprising allegations from his first book in favor of turning his best friends in first, which makes him an even bigger dick.


"Raise your hand if you're a dick."

It's hard to believe that this is the same guy who once saved a woman and all her appliances from a burning building. Sure, that was an episode of The Simpsons, but it's about the only good thing Canseco has ever done in his life. Canseco's penchant for douchery extends beyond the realms of using steroids to cheat at baseball, connecting other people to steroids so they too could cheat, then turning them all in for a fat paycheck.

Both of his wives have cited him for domestic violence, and both later divorced him. His second marriage was the classic American love story; boy meets girl working at Hooters, boy marries girl, boy hits girl, boy is arrested and put on probation, girl divorces boy, girl poses in Playboy using his last name. If those kids couldn't make it work, what chance do the rest of us have?

There's more to the story, like when he tried to blackmail Magglio Ordonez into giving him money to keep his name out of his second book. We emailed Bob Woodward to see if he ever tried blackmailing Gerald Ford, but he didn't get back to us. The Canseco saga does have a happy ending though. Jose recently lost a "celebrity" boxing match to former NFL player Vai Sikahema in which Canseco was knocked out in the first round. Now if there was only some way we could make that happen seven or eight hundred more times we'd be good.


"Waaaahhhh."

#10. Charles Comiskey:

Comiskey is best known for being the former owner of the Chicago White Sox, and for their field which was named after him, before it was changed to U.S. Cellular Field in honor of Ulysses Stanton Cellular.

However, back in the day, he was best known for being a miserably cheap bastard. It stands to reason that if you own a professional sports team, you have a shitload of money, and if you spend that money to buy a sports team, something that is utterly frivolous, it stands to reason that to cheap out on running that team makes you quite the douchebag. It's just logic.

Charlie Comiskey was one such douchebag, paying his players substandard wages in a time before free agency, when they had no choice but to accept them. He promised one of his pitchers a $10,000 dollar bonus if he won thirty games in a season, but benched him right before he could reach that mark, preferring to save the money at the risk of losing some games. Also he wouldn't pay for his player's laundry. To reiterate, he bought a professional sports team, built them a stadium, then decided he'd rather they look like hobos than pay for laundry.

Of course, his stinginess ended up leading to the Black Sox Scandal, in which his team threw the World Series for cash. Cash, that one can presume went toward not smelling like shit.

#9. John McGraw:

John McGraw was a decent player, but as a manager he was a well-known innovator and is credited with inventing the hit and run. He also is credited with being a mean-spirited prick.

Gentlemanly conduct was a foreign concept to McGraw, who as a third baseman was known for his aggressive and undeniably immature ways of stifling opposing runners. Have you ever played with a drunk friend at a softball game who thought it'd be funny to trip people when they were running the bases and tug on people's shirts to keep them from leaving the base? Well that was McGraw, all the time, and there's a very real possibility he wasn't even drunk when he did it.


It's unfortunate that the only available pictures of McGraw show him shaking hands.

As a manager he was just as big of a douche, constantly picking fights with anybody he could, including the fans, who would in turn throw rocks and bottles at the players. The players had to get pelted with dangerous objects just because they played for this guy.

He seemed to embrace being a manager purely because it gave him a chance to wage psychological warfare on the players under him (one coach on the Giants said McGraw "...eats gunpowder every morning for breakfast and washes it down with warm blood.")


See? That doesn't make him look like a dick at all. Clever, McGraw.

McGraw actually held one major league record that stood for 75 years: the most times getting kicked out of a game. Between his time as a player and a manager, an incredible 131 times umpires decided McGraw was just acting like too much of an ass to stay on the field.

John McGraw: great at managing, even better at being a dick.

#8. Roger Clemens:

Remember when Roger Clemens was known for being a great pitcher, perhaps one of the best of all time, and the worst thing anybody had to say against him was that one time he threw a piece of a bat at Mike Piazza? We bet Roger longs for those days.

Some think Clemens' legacy has been tainted by steroids even moreso than Barry Bonds'. First came the adamant denials about steroid use, including such delicious bon mots along the lines of "If I had been using steroids I'd be pulling tractors with my teeth and have a third ear growing out of my forehead" a statement that, while asinine and condescending, also blew our fucking minds with it's utter lack of logic.

Clemens then threw one of his best friends (and steroid supplier) Brian MacNamee under the bus, even taping a conversation with him to save his own ass (it didn't). Oh, also there were all the affairs he's had including one with the wife of professional golfer/beer drinker John Daly and one with country singer Mindy McCready that started when she was fifteen.

We do think Clemens belongs in the Hall of Fame, if there is in fact a Hall of Fame for douchebags somewhere.

#7. Tom Yawkey:

Yawkey owned the Boston Red Sox from 1933-1976 and the street which Fenway Park resides on is named in his honor, a tribute to a man of fortitude and conviction. Unfortunately, one of those convictions was blind, fervent racism.

Yawkey has the distinction of being the last owner to integrate his ball club, when he reluctantly let Pumpsie Green put on the Red Sox uniform and stroll out onto the field in 1959, which, to be fair to Yawkey, was a mere 12 years after Jackie Robinson broke the color barrier. That's just a smidge over a decade, right?


"Look, Honey, a Negro. Gross, right?"

That's what earns Yawkey the title of one of the biggest assholes in the Baseball Hall of Fame: determination. Ridiculous, sad, racism-fueled determination. For you see, while other teams were integrating and providing themselves with the best collection of athletes possible, Yawkey stuck with the same old white guys that had worked so well at not winning him a single World Series all those years.

They had been at the very least a contender in the salad days of segregation. Once other teams started to incorporate black players in their line up, the Red Sox started a precipitous fall down the standings board. Lesser racists would have seen the writing on the wall, or perhaps mustered up some simple human decency and accepted the fact that these black players were just as good as their white counterparts.

However, good ol' Tommy rose above all that and proceeded to keep his team the way it was, and the Red Sox proceeded to finish 10+ games out of first place from 1950 until 1966. For sticking to his racist guns at the cost of his team's success, truly Tom Yawkey is worthy of the the title "Douchebaggiest Owner in Baseball History".

#6. Keith Hernandez:

Today, mustache aficionado Keith Hernandez is probably best known now as a hair dye spokesperson and for the two-part Seinfeld where he almost banged Elaine. However, before that he was a five time all star, 1979 NL co-MVP, and perhaps the best fielding first basemen of all time. Also he loved him some nose candy.

Yes, Mr. Hernandez was known for his use of the cocaine which led to his involvement in the famed Pittsburgh drug trials. Of course his own substance abuse doesn't make him an asshole, but his destructive influence on young Mets teammates Dwight Gooden and Darryl Strawberry sure does. You may remember Gooden and Strawberry as the talented young stars whose bright careers were derailed by drug and alcohol abuse. You know what probably contributed to that? Hernandez telling Strawberry the best way to break out of a slump is to go out and get shitfaced.

Hernandez didn't stop being a dick when his career ended though. In 2006 he was calling a game between the Mets and Padres when he happened to spy Padres team massage therapist Kelly Calabrese in the dugout. Keith's response? "I won't say women belong in the kitchen, but they don't belong in the dugout." It's true Keith doesn't think women belong in the kitchen. He thinks they belong in his bedroom, feeding him slices of papaya, when not servicing him sexually of course.

Needless to say, Hernandez's comment caused a bit of an uproar, but to be fair he apologized. Apologized by saying "You know I am only teasing. I love you gals out there, always have." You stay classy, Keith.

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