Jon Gruden met Cindy Brooks in 1985 when he was a young, ambitious graduate assistant at the University of Tennessee, and she was a student with a passion for education and cheerleading. Their relationship grew quickly, with football and mutual admiration at its core. By July 6, 1991, they were married, sealing a bond that would last more than three decades.
On a professional front, Jon Gruden’s coaching journey saw him rise from assistant roles with the Green Bay Packers and Philadelphia Eagles to becoming the head coach of the Oakland Raiders in 1998. He later led the Tampa Bay Buccaneers to their first Super Bowl victory in 2002, becoming the youngest head coach to win a championship at the time. After a decade-long hiatus from coaching, he returned to lead the Raiders again in 2018. His career has been marked by both triumph and controversy, including his resignation in 2021 following the leaked emails scandal.
Most recently, in March 2024, Jon Gruden joined the Milano Seamen of the European League of Football as an advisor, marking his return to the sport in a new capacity. In February 2025, Gruden’s name resurfaced in NFL discussions, with speculation about him potentially joining the New Orleans Saints as an offensive coordinator under newly appointed head coach Kellen Moore. His past coaching experience and ties with Saints quarterback Derek Carr have fueled the conversation, though no official decision has been made.
Who Is Jon Gruden’s Wife? All About Cindy Brooks
Jon Gruden has been married to his wife Cindy Brooks since July 6, 1991, after meeting her in 1985 at the University of Tennessee, where she was a cheerleader and he was a graduate assistant. They have three sons (no daughter despite online speculations): Jon II (Deuce), a strength coach and powerlifting champion, Jayson, and Michael, all of whom share a strong bond with their father.
Cindy, who had been part of the university’s cheerleading squad, brought an energy that complemented Gruden’s fiery coaching spirit. She earned a degree in educational administration, but her interests extended beyond academics—she studied classical piano and music education, adding another dimension to her personality. Over the years, she worked as a teacher at the National Cheerleaders Association, helping young athletes hone their skills and discipline.
While Jon Gruden’s career took him from college football to the NFL, Cindy became heavily involved in philanthropy, working with various charities and even creating an online course for the University of Tennessee during the pandemic.
The couple has three kids: Jon II, known as Deuce, Jayson, and Michael. Deuce, the eldest, followed closest in his father’s footsteps. He became an assistant strength and conditioning coach for the Raiders, making a name for himself in the fitness and sports performance world. More than just a coach, he’s a competitive powerlifter and proved his strength by winning gold at the 2017 IPF World Classic Powerlifting Championships in the junior 83kg weight class. His dedication to both football and weightlifting speaks to the intensity that seems to run in the Gruden bloodline.
Jayson and Michael, while less public figures, also share a strong bond with their father. The family dynamic has always been centered around sports, discipline, and an unrelenting drive for excellence. Despite Jon’s demanding coaching career, which took him from the Green Bay Packers to the Oakland Raiders, Tampa Bay Buccaneers, and eventually back to the Raiders, Cindy maintained a steady presence in their children’s lives, ensuring they had a strong foundation.
Jon Gruden’s career, filled with highs and controversies, inevitably affected his family, but Cindy remained a pillar of strength. In 2021, when Jon’s tenure with the Raiders came to an abrupt end due to the leaked emails scandal, Cindy stood by him. It was a moment that tested their marriage, but their decades-long relationship weathered the storm. Despite the professional setbacks, the Grudens continued their life in Las Vegas, maintaining their close-knit family dynamic.
One of the more humorous and unexpected moments involving Cindy occurred during the 2020 NFL season when Raiders quarterback Derek Carr audibled “Cindy Gruden Tiger Woods” during a game. The phrase caught Jon Gruden’s attention, leading him to jokingly warn Carr to “keep my wife out of it.” The moment became a lighthearted distraction during an otherwise intense season and showcased the casual but firm way Jon handled even the most unexpected situations.
Throughout the years, Cindy’s role as both a wife and mother has been one of unwavering support. She has not only been involved in charity work but has also been a constant presence at games and events, often seen cheering on her husband and sons. Her commitment to education, philanthropy, and family is a testament to the balance she has maintained despite the rollercoaster ride that comes with being married to an NFL coach.
Their journey together has been anything but ordinary. From a college romance to raising three boys, navigating Super Bowl victories, job losses, scandals, and personal triumphs, Jon and Cindy Gruden have built a life that is deeply rooted in perseverance. Their sons, particularly Deuce, have carried forward the family’s competitive nature, while Cindy’s influence has kept them grounded. No matter where Jon’s career takes him next—whether back into coaching or remaining in football analysis—the Gruden family remains a tight unit, shaped by the passion and intensity that define their name.
