Mike Ditka
What hasn’t “Iron Mike” done? Player? Check. Coach? Check. TV commentator? Check. Ditka was an NFL champ with the 1963 Bears, and is also a three-time Super Bowl champ, playing on the Cowboys Super Bowl VI team as well as winning as an assistant coach for the Cowboys in Super Bowl XII, and coaching the Bears to victory in Super Bowl XX. He was also impressively named to both the NFL’s 50th and 75th Anniversary All-Time Team. Ditka and Tom Flores are the only people to have ever won an NFL title as a player, an assistant coach, and a head coach. With all of that, he has no worries over auto insurance as he’s racked in tons of money.
Mike Tomlin
Mike Tomlin is actually the fifth youngest head coach in any of the four major North American professional sports, nice! He is also the tenth African-American head coach in the history of the NFL, and the first in Steelers history. With the victory in Super Bowl XLIII on February 1, 2009 in his belt against the Arizona Cardinals, he became the youngest head coach to lead his team to a Super Bowl championship. He also has four division titles to his name and he’s only been in the big leagues since 2007.