Active: 1973-1995
Teams: Yankees/Padres/Angels/Twins/BlueJays

Drafted by MLB, the NFL, and the NBA, Winfield is probably the best athlete on this list, and gets a badass nod for that alone. That he indirectly got George Steinbrenner suspended from baseball (when he got the Boss so mad at him that Steinbrenner hired a mobster to dig up dirt on him), and that that suspension indirectly won the Yankees a bunch of World Series (because the Boss wasn't around to sign the Danny Tartabulls of the world)—well that's even more badass.