John Madden
John Madden coached the Oakland Raiders in his entire career, racking up a whopping 76% winning percentage, winning a Super Bowl, seven division titles and an induction into the Pro Football Hall of Fame. He has never had to worry about auto insurance a day in his life as he’s still earning loads as a sports commentator.
Joe Gibbs
Gibbs was the 20th and 26th head coach for the Washington Redskins, under him, the Redskins had eight playoff appearances, four NFC Championship titles, and won Super Bowl XVII, XXII, XXVI. Personally, he’s a two-time NFL Coach of the Year and was inducted to the Pro Football Hall of Fame, class of 1996. He is a true football legend.