Team(s): New York Yankees
Years of ownership: 1973-2010
Craziest incident: Hiring a gambler to dig up dirt on Dave Winfield.

There's only one Boss, and George Steinbrenner set the gold standard for eccentric ownership. His acts of lunacy are almost too numerous to mention here, but we'll take a stab at it anyway. He went through 19 different managers between 1973 and 1990, hired/fired Billy Martin a total of five times, pleaded guilty to obstruction of justice and making illegal campaign contributions to Richard Nixon (which got him banned from baseball for 15 months), hired a goon to dig up dirt on Dave Winfield, who happened to be one of his own players (he earned a permanent ban from day-to-day management of the Yankees for that one), and throughout his time in charge was prone to ripping anyone and everyone publicly. It's safe to say he is a certified legend.