Jon Gruden was a longtime NFL coach and ESPN broadcaster who reportedly resigned Monday after reports revealed his use of racist, homophobic and misogynistic remarks in emails before he became the head coach of the Las Vegas Raiders.

Gruden won a Super Bowl while he was the head coach of the Tampa Bay Buccaneers and parlayed that into a successful broadcasting career in which he was a major part of the company’s "Monday Night Football" broadcast and his famed "Gruden’s QB Camp."

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In the days leading up to his dismissal, the Raiders were being considered a possible contender for the AFC West crown. The Wall Street Journal obtained an email from Gruden in 2011 showing him using a racist troupe to describe NFLPA executive director DeMaurice Smith.

It snowballed from there Monday when The New York Times published more comments from Gruden in the years before he was coach of the Raiders.

Here’s what else you need to know about Gruden.

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Family coaching tree

Washington Redskins head coach Jay Gruden (right) fist bumps his brother, Jon Gruden, during their final round of organized team activities on June 11, 2014 in Ashburn, VA.  (Photo by Jonathan Newton / The Washington Post via Getty Images)

Gruden’s father, Jim, was a quarterbacks coach and director of player personnel for the Buccaneers. His brother, Jay, was an arena football coach and former head coach of the Washington Football Team.

Played college football

Gruden transferred to Dayton from Muskingum College in Ohio. He was mostly a backup for the Flyers and later graduated with a degree in communications.

JON GRUDEN RESIGNS AS RAIDERS HEAD COACH AFTER HOMOPHOBIC, MISOGYNISTIC EMAILS REVEALED

College coaching career

Gruden broke into the college ranks with Tennessee where he served as a graduate assistant from 1986-1987. He would then serve as the passing game coordinator for Southeast Missouri State in 1988 and a tight ends coach for Pacific before finally getting a shot in the NFL in 1990. He would be back in college at Pittsburgh in 1991 as a wide receivers coach before staying in the pros for good.

NFL assistant

Gruden took a few assistant coaching jobs before he got his start with the Raiders. He was an offensive assistant for the San Francisco 49ers and then he was an offensive assistant/quality control coach and wide receivers coach for the Green Bay Packers from 1992 to 1994. He also served as the Philadelphia Eagles’ offensive coordinator from 1995-1997.

NFL head coach

Coach Jon Gruden of the Tampa Bay Buccaneers watches play against the Tennessee Titans at Raymond James Stadium on October 14, 2007 in Tampa, Florida.  The Bucs won 13-10. (Photo by Al Messerschmidt/Getty Images)

Gruden got his first crack at being a head coach with the Raiders in 1998 when the team was still in Oakland. He served as their coach from 1998-2001 before being traded to the Buccaneers as the replacement for Tony Dungy. Gruden was the Buccaneers’ head coach from 2002-2008. He would lead the team to a Super Bowl title over the Raiders in 2002. He would finish his tenure as the winningest coach in Bucs history and was inducted into the Bucs’ ring of honor.

He was fired by the Bucs in 2009 and later joined ESPN. After years at ESPN, he re-joined the Raiders on a 10-year, $100 million contract in 2018. He left the team on Oct. 11, 2021.

ESPN career

Members of the Monday Night announcing crew Ron Jaworski, John Gruden and Mike Tirico of ESPN look on during the game between the New England Patriots and the New York Jets at Gillette Stadium on December 06, 2010 in Foxboro, Massachusetts. The Patriots defeated the Jets 45 to 3. (Photo by Rob Tringali/SportsChrome/Getty Images)

Gruden replaced Tony Kornheiser as the color commentator for "Monday Night Football" broadcasts. He would serve as a commentator for NFL and postseason college football games from 2009-2018. ESPN told The New York Times the emails were "clearly repugnant under any circumstance."

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Email scandal

Head coach Jon Gruden of the Las Vegas Raiders talks with quarterback Derek Carr #4 during their game against the Miami Dolphins at Allegiant Stadium on September 26, 2021 in Las Vegas, Nevada. The Raiders defeated the Dolphins 31-28 in overtime.  (Photo by Ethan Miller/Getty Images)

The Wall Street Journal first obtained an email from Gruden from 2011 as part of the NFL’s workplace investigation into the Washington Football Team. He used a racist troupe to describe NFLPA executive director DeMaurice Smith. The New York Times then released more emails showing Gruden’s history of homophobic and misogynistic remarks along with comments aimed at Roger Goodell. The emails were between him and then-WFT president Bruce Allen during his time at ESPN.