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warshawlawI'm talking criminals, crooks, racists, clubhouse poison, etc., but who also exhibit the best combo of playing skills and jerkiness.  
C: Ray Schalk: Not a criminal or druggie but by all accounts a very unpleasant person to deal with as a teammate.  
1B: Hal Chase: as crooked as they come.  
2B: Rogers Hornsby: Such an A-hole he was traded 2x in 3 seasons despite averaging what, .350, during that time?  When you have to hit .400 to keep your job, you must be a real piece of work.  
SS: Any ideas here?
3B: Pete Rose.  
RF: Albert (don't call me Joey) Belle.  Biggest jerk of the '80s.  
CF: Ty Cobb.  Among his better known feats are beating a cripple, braining a black man who had the temerity to speak to him and so offending his contemporaries that they refused to deal with him after their playing days were over.  
LF: Joe Jackson.  He may have been ignorant, illiterate and kinda dumb, and yes Comiskey screwed him, but he did take the bribe money and sat in conspiracy with cheats.  
P: Eddie Cicotte: 'nuff said
P: Steve Howe: aka if it's white it goes up my nose
P: Denny McLain: when you owe him money, you REALLY better pay him.  
P: LaMarr Hoyt:  Another "nosey" guy.  
MGR: Tris Speaker.  Had to work him in somewhere for KKK membership and fixing a game with Cobb.  
GM: George Weiss, Yankees: Univerally reviled among those who dealt with him.
Owner:  I could be sentimental and go with Comiskey, but I have to go with Steinbrenner.  
Commissioner: Another tough choice. Do we go with the imperious Landis who never heard of due process or fairness (to wit, Buck Weaver), or perhaps the Babe's shill Ford Frick*?  No, I have to go with Bowie Kuhn for the sheer combination of arrogance and stupidity.  
Honorable mentions: Darryl "White Lines" Strawberry, Jose "Baby You Can Drive My Car But Stay Out Of Discos" Canseco, Dave "I Didn't Know It Was a Transvestite Hooker" Stewart, Ken "Crack" Caminiti, Barry "Half The Clubhouse Is Mine And It Was Flax Seed Oil" Bonds