Jon Gruden & Cindy Gruden, Together For 36 Years

In 2021, the American football coach Jon Gruden made news after quitting his job at the Las Vegas Raiders. One of the most experienced men in the game, he started working as a manager in the mid-’80s and went all the way from being a Tennessee graduate assistant to becoming an NFL head coach. To this day, winning the Super Bowl XXXVII remains his proudest feat.

Gruden met his wife Cindy in 1985, and the two tied the knot in 1991. Together for a long, long time, the two lovebirds have three children, all boys. One of their sons, Jon II, worked alongside his dad as a conditioning assistant.