Jon Gruden

Gruden met his wife, Cindy Brooks, in 1985 while he was working as a graduate assistant and she was a student and cheerleader at the University of Tennessee. The couple married in 1991 and have three sons: Jon II (known as Deuce), Michael, and Jayson. Their eldest son, Deuce, became an NFL assistant strength and conditioning coach and was a competitive powerlifter who won a gold medal at the 2017 IPF World Classic Powerlifting Championships in the junior 83 kg weight division.

Gruden grew up in a football-oriented family of Slovene descent. His father, Jim Gruden, worked as a college and professional coach and scout, serving as an assistant coach at Indiana University and the University of Notre Dame before working in player personnel and coaching for the Tampa Bay Buccaneers and San Francisco 49ers. Jon's younger brother, Jay Gruden, had an extensive career as a quarterback and head coach in the Arena Football League before serving as head coach of the Washington Redskins, while his brother James became a radiologist and medical professor.

Gruden played quarterback at Muskingum College before transferring to the University of Dayton, where he served as a backup quarterback and three-year letterman from 1983 to 1985. After graduating with a degree in communications in 1986, he entered the coaching ranks as a graduate assistant at the University of Tennessee. He subsequently worked as an offensive assistant and position coach at Southeast Missouri State, the University of the Pacific, the San Francisco 49ers, and the University of Pittsburgh.

In 1992, at age 28, Gruden entered the NFL coaching ranks full-time under Mike Holmgren with the Green Bay Packers, serving as an offensive assistant and wide receivers coach. In 1995, he became the youngest offensive coordinator in the NFL when Ray Rhodes hired him for the Philadelphia Eagles. In 1998, Oakland Raiders owner Al Davis hired the 34-year-old Gruden as head coach. During his first tenure in Oakland from 1998 to 2001, Gruden led the team to consecutive AFC West division titles in 2000 and 2001. His intense sideline demeanor and animated expressions led Raiders defensive lineman Grady Jackson to give him the nickname "Chucky," referencing the horror movie character.

In February 2002, the Tampa Bay Buccaneers acquired Gruden from Oakland in an unusual trade involving four draft picks and $8 million in cash. In his debut season with Tampa Bay, Gruden overhauled the offense to complement the franchise's top-ranked defense, directing the Buccaneers to a 12-4 regular season record and a berth in Super Bowl XXXVII. Tampa Bay defeated Gruden's former team, the Raiders, 48-21 to secure the franchise's first Super Bowl title. At age 39, Gruden was the youngest head coach in NFL history to win a Super Bowl at the time.

Gruden coached the Buccaneers through the 2008 season, compiling a 57-55 regular-season record and winning three NFC South division titles (2002, 2005, and 2007). Although his teams captured division crowns with quarterbacks such as Brad Johnson and Jeff Garcia, postseason appearances following the championship season ended in early-round exits. After the Buccaneers lost their final four games of the 2008 campaign to miss the playoffs, Gruden was dismissed in January 2009 as the winningest coach in franchise history.

Following his departure from Tampa Bay, Gruden joined ESPN in May 2009 as a color analyst for Monday Night Football, replacing Tony Kornheiser. Gruden became a mainstay of the network's football coverage for nine seasons, contributing to NFL draft telecasts, college bowl games, and special features. He also hosted the popular annual series Jon Gruden's QB Camp, conducting film-study sessions and development interviews with prospective NFL quarterback draft picks.

During his time away from the sidelines, Gruden established the Fired Football Coaches Association (FFCA) in Tampa, Florida. The organization operated as a football strategy think tank and film archive where high school, collegiate, and professional coaches and players gathered to review game film and discuss offensive and defensive philosophies. Gruden maintained and updated his own playbooks and analytical studies at the facility until he returned to active NFL coaching in 2018.

In January 2018, Gruden returned to the Raiders as head coach after signing a 10-year, $100 million contract, leading the team through its final seasons in Oakland and its subsequent relocation to Las Vegas in 2020. His second tenure concluded five games into the 2021 season when he resigned on October 11, 2021, following the public disclosure of emails sent between 2011 and 2018 containing racist, misogynistic, and homophobic language. Gruden subsequently filed a lawsuit against the NFL and Commissioner Roger Goodell regarding the disclosure of the communications.

Following his resignation, Gruden was initially removed from the Tampa Bay Buccaneers Ring of Honor in 2021, though the team announced his reinstatement in February 2025. He continued to participate in football in advisory capacities, consulting for the New Orleans Saints coaching staff in 2023, advising the Milano Seamen of the European League of Football in 2024, and joining Barstool Sports as a media contributor in late 2024.