Age: 77
Title: Principal Owner, New York Yankees
Pro: Cares about one thing—winning the World Series—and will spend whatever it takes to do it.
Con: Despite a $195 million payroll, the Yankees are waaaaay back in the AL East and haven't won a World Series in seven years. The Boss is also a a world class meddler (Billy Martin: you're fired, hired, fired), though fading health has kept him off New York's back pages in recent years.