Did Jon Gruden win a Super Bowl? Former NFL HC's career

There's every chance that Jon Gruden's resignation as head coach of the Las Vegas Raiders brings an end to his colorful and notable 20-year coaching career in the NFL.

Gruden walked away from the Raiders four years into a 10-year contract on Monday after reports surfaced about emails he had sent during the course of his career that contained homophobic, mysoginistic and racist comments.

Jon Gruden had been out of the coaching game for a decade between 2008 and 2018, serving as ESPN's head analyst on Monday Night Football, while also heading up the network's NFL Draft coverage and postseason college football games.

But way before his recent ill-rated, four-year spell with the Raiders, during which time the team relocated from Oakland to Las Vegas, Gruden had a 10-year run as an NFL head coach. That followed seven years in the league as an offensive coordinator, wide receivers coach and offensive assistant for the likes of the San Francisco 49ers, the Philadelphia Eagles and the Green Bay Packers.

Which team did Jon Gruden win a Super Bowl with?

While his NFL career may have ended in an ignominious manner, the highlight of Jon Gruden's career will no doubt be Super Bowl XXXVIII.

After earning his first head coach job with the Raiders in 1998, Gruden took the team to the AFC Championship game in 2000, losing out to the Baltimore Ravens. They went back to the postseason in 2001, this time getting beaten in the divisional round by first-year starter Tom Brady and his New England Patriots.

Jon Gruden's first stint in silver and black also ended in a shocking manner. After the Tampa Bay Buccaners fired Tony Dungy and failed to land their first head coach target Bill Parcells, the Bucs mounted a high-stakes trade for Gruden — sending two first-round picks, two second-round picks and an $8 million payment to Oakland.

Gruden penned a five-year contract and, in his first year in Tampa in 2002, he led the Buccaneers one step further than what he had managed with the Raiders — to the Super Bowl. The team that Gruden and the Bucs would face in the big game? The Oakland Raiders, now led by Bill Callahan.

The Raiders went into the game as favorites by four points but, much like Gruden's Buccaneers did through the rest of the playoffs, they blew away the AFC champions by a score of 48-21. At the time, aged 39, Gruden became the youngest coach to lift the Lombardi Trophy and both Gruden and the Buccaneers became Super Bowl champions for the first time.

Jon Gruden coached six more seasons in Tampa Bay but never won another playoff game, and did not return to the knockouts during his second spell with the Raiders. That Super Bowl triumph in San Diego in 2022 was his last NFL postseason victory.