25. Randall Simon
Career Years: 1997-2004
Career Lowlight: Arrested for tapping/assaulting woman in sausage costume with a bat.
Simon's eight seasons in Major League Baseball were pretty unremarkable, and he petered out in Japan and lesser domestic leagues, as many do. However, one night in July of 2003, he became a legend when he used his bat to tap the top of one of the sausages during the Brewers' signature race, causing the woman wearing the suit to fall down and scrape her knee. A seemingly innocuous (if stupid) joke sustained the 24-hour sports news cycle for several days, and Simon was even questioned by police in the matter. It is one of the stranger legacies a baseball player has ever left upon the game.