Jon Gruden won a Super Bowl. He got the ring, the parade, the validation every coach chases. However, looking back at how he was shipped to the Tampa Bay Buccaneers, he didn’t want the opportunity at first glance.

“That was an emotional time for me,” Jon Gruden said on the Not Just Football podcast. “I didn’t really want to get traded, but we had a contract dispute. I’m from Tampa, and my dad coached for John McKay with the Buccaneers. My dad was the personnel director for the Bucs, and he drafted Steve Young and Bo Jackson. We have some really cool ties to Tampa Bay, so I was fired up and motivated to come down here.

“I was obviously a little concerned without having any picks to build your team with, but we got to work with Derek Brooks, Warren Sapp, Simeon Rice, John Lynch, and Barber, and we got the offense clicking just enough to do some damage in the postseason.”

The Gruden move went down at 3 a.m. on Feb. 18, 2002, and Tampa Bay paid a steep price. In exchange for the former head coach, Tampa Bay gave up first-round picks in 2002 and 2003, second-round picks in 2002 and 2004, and $8 million. On top of that, Gruden’s salary more than tripled, jumping to nearly $4 million a season for five years, according to ESPN.

Tampa Bay’s General Manager, Rich McKay, actually wanted defensive coordinator Marvin Lewis instead. However, the Glazer family, who own the Bucs, wanted someone to rebuild their offense.

By that time, Gruden had posted two terrific winning seasons with the Oakland Raiders, after finishing 8-8 in his first two years as head coach. He’d done enough to warrant perhaps a higher salary; there was indeed a contract dispute, as noted by The Athletic in a report. Gruden had put the Raiders back on the map after a long time. However, then-general manager Al Davis thought otherwise.

Bucs co-chairman Bryan Glazer regarded this move to have “shaken the NFL.”

Eleven months later, Gruden was standing across from his old team in Super Bowl XXXVII. Ironically, Gruden bested his former team, the Raiders, in the final game with a 48-21 score, giving the franchise its only Lombardi Trophy. At 39, Gruden became the youngest head coach ever to win the Super Bowl at that time.

His tenure with Tampa Bay lasted till 2008, and he became the winningest coach in franchise history (57-55). In 2017, the Buccaneers brought him back to induct him into the team’s Ring of Honor at Raymond James Stadium.

Gruden returned to Oakland in 2018, back with the team he’d left behind all those years earlier. But that second stint ended on an unceremonious note. He resigned during the 2021 season after the email controversy.