Jon Gruden & Cindy Gruden – 36 Years

One of the most experienced managers in the NFL, Jon Gruden, made headlines in 2021 after resigning from his position as the head coach of the Las Vegas Raiders. It’s but a mishap in a long career that’s been anything short of successful, and that’s allowed Gruden to become a Super Bowl champion.

His personal life’s not going so bad either: the iconic NFL coach’s been married to his wife Cindy since 1991, and the two have been an item since 1985. Together for over three decades, they welcomed three sons to the world. One of them, Jon II, worked alongside his dad at the Las Vegas Raiders.