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.

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 p***k.

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.

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 f*****g minds with it's utter lack of logic.

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 n***o. 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.

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 a*****e, 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.

5

Ugueth Urbina:

While probably the least well-known person on this list to the casual baseball fan, Urbina was still a solid player, racking up 234 career saves, winning a World Series in 2003, then retiring to his native Venezuela where he sat on a rocking chair on his patio, drinking sweet tea, and committing attempted murder. Yes, attempted murder.

For you see, one day Ugueth had a bit of a scuffle with five farm workers on his property, and well things got a little bit heated. So what was Urbina to do? Why, grab a machete and start chopping some motherfuckers, that's what. While the machete approach proved unfruitful, Urbina was a determined man and he remembered the old adage: If at first you don't succeed (to brutally murder people with a machete) try, try again (by means of attempting to set them on fire).

4

Kenesaw Mountain Landis:

You would think a man who had Mountain for a middle name would be pretty badass, but you'd be wrong. Oh, he was ornery for sure, but badass, no dice. Unless you just drank a shot of paint thinner, you'll remember the Charlie Comiskey entry. Well, the man who is responsible for the lifetime ban of every member of the 1919 Chicago White Sox? Commissioner Landis, of course. Even when it became obvious that some of the members were innocent of any wrongdoing, Landis refused to reinstate them. And if you thought that was the worst thing he ever did, you haven't heard his motto: Tough on gambling, tougher on black people.

Landis is probably the main reason the color line stayed in baseball for as long as it did. He was baseball's first commissioner, serving from 1920-1944, and he picked up right where he left off as a judge, when he got black boxer Jack Johnson banned from boxing for life for transferring a white woman over state lines.

Many times people petitioned Landis to allow black players in the major leagues, and every time Landis voted it down, then presumably leaned back in his throne of skulls and drank the blood of kittens. Mercifully, his tyrannical reign came to an end in 1944 the way all tyrant reigns end; with his death.

3

Marge Schott:

Schott will live on in baseball infamy because of one phrase, her little pet name for her black players: Million Dollar "N-words". Of course, she didn't have the tact or simple human decency to censor the phrase as such.

Other than on the field however, no black people were allowed to be hired by the organization. Not one. Her racism wasn't saved for just black people, however. She also had it out for the Jews, and she even admitted to owning a Nazi armband, and didn't see a problem with it, and also said she didn't see why the racist slur "j*p" is offensive.

Quick posthumous tip for you, Margie: Want to know why the phrase is offensive? Because Japanese people are offended by it, you horrible, horrible b***h.

Enough offenses for you? No? OK, howsabout this; she wouldn't let her players wear earrings because "only fruits wear earrings." Probably the least egregious thing she ever did in her life was let her St. Bernard, Schotzie, run around on the field all it damn well pleased, which of course led to big steaming piles of dog s**t being left on the field.

Seriously, Reds players often complained about having to avoid stepping in dog s**t while playing in professional baseball games. When one of the nicer things you ever did in your life was make your players play on a dog s**t-laden field, you truly deserve the title of one of the biggest assholes in baseball history.

2

Barry Bonds:

You knew he'd show up here eventually.

The breaking of an all-time record is usually a joyous thing. It makes grown men cry, women swoon, and dogs hump trees like there is no tomorrow. So what happened when Barry Bonds broke Hank Aaron's all-time home run record, perhaps the most hollowed record in ALL of sports, not just baseball? A lot of people got pissed. That's how much Barry Bonds is hated.

There are two universal truths people know about Barry Bonds; One, he is the face of the steroids era and two, he is a huge dick to pretty much everybody. Barry is known to be one of the worst teammates possible and openly hostile with the media. In college, he feuded with teammates and his manager. In Pittsburgh, he feuded with teammates and his manager. In San Francisco he was given essentially half the locker room to himself and big comfy recliner chairs out of the hope he wouldn't b***h.

When Bonds is not enjoying being a totally arrogant dick to teammates and reporters, he likes to spend his down time with his family. Or his mistress, Kimberly Bell, whom he had an affair with from 1994 until 2003, which means it started about the time he divorced his first wife, left him undeterred from getting married in 1998, and kept on keeping on. In Barry's defense though, at least he was nice enough to buy her a house in Arizona. So he had a place to bang her.

Now, you may be asking, "Well this is all fine and dandy, but do you have any crazy anecdotes that make Bonds seem incredibly immature to the point of pyschosis?" To which we retort, do we ever!

1

Ty Cobb:

What's there about this man that wasn't detestable? During his career he stole a lot of bases, which is impressive. Of course, the fact that he sharpened his metal cleats and was not shy about gouging them into a man's leg if they got in his way of stealing a base probably helped out a tad on that front.

Then of course, there was the racism, which to be fair was no more virulent than your average southern folk back in the day, and certainly we have let the repulsively racist actions of those in the past slide in favor of other attributes on the occasion in the country (see Jefferson, Thomas). Plus, there is a distinct chance he fixed a game or two in his day.