Jon Gruden timeline to resignation: How Raiders coach went from 10-year deal to early exit from Las Vegas

Jon Gruden resigned as Raiders coach on Monday, just three days after the Wall Street Journal reported he was under investigation for using a racial trope in a 2011 email and just an hour after The New York Times revealed that other Gruden emails over a span of eight years included misogynistic, homophobic and sexist language. The former Super Bowl champion was not even four full seasons into the 10-year contract he signed with Las Vegas back in 2018.

How in the world did we get here? Here's a birds-eye-view timeline of Gruden's abrupt return -- and departure from -- the NFL:

Gruden spent 11 years as a head coach between the Raiders (1998-2001) and Buccaneers (2002-08) before nestling into post-coaching life, most famously as a color commentator on ESPN's "Monday Night Football." After nine years away, he made his return with a luxurious welcome from Raiders owner Mark Davis, complete with a historic 10-year, $100 million contract.

Before setting foot on the sidelines for a real game in his second stint with the Raiders, Gruden signed off on the departure of arguably the team's best player in Mack, who couldn't strike a long-term deal with the club. Out went his top pass rusher, along with two draft picks, and in came a package of four picks.

With Mack gone, Gruden shipped another young centerpiece away, this time dealing his No. 1 wide receiver to the Cowboys in exchange for a first-round pick, opting to unofficially punt on 2018 in hopes of rebuilding the team from the ground up.

Just 3-10 through his first 13 games, Gruden said goodbye to the general manager who helped welcome him back to the NFL. This paved the way for more Gruden control in the front office, and ...

The former NFL Network draft expert replaced McKenzie as Gruden's right-hand man, essentially resetting the clock on the Raiders' rebuild. The duo's boldest move of their first offseason together, however, proved to be more trouble than it was worth ...

A perennial All-Pro with the Steelers, Brown successfully talked his way out of Pittsburgh following a bizarre falling-out in Steel City, and Gruden signed off on his acquisition, sending two draft picks for the wideout. Brown never took a snap for the Raiders, however, requesting and receiving his release just days before the 2019 opener following a tumultuous offseason that included missed practices, threats of retirement and a reported confrontation with Mayock.

Looking to build off his 7-9 performance in 2019, his second straight losing season at the helm of the team, Gruden was docked $100,000 for failing to properly wear a face covering, as regulated in the NFL's pandemic protocols, during a Week 2 win over the Saints.

Found to be in repeated violation of COVID-19 protocols, Gruden received another $150,000 fine from the league office. On the field, meanwhile, his Raiders improved to 6-3 before losing five of their final seven games, ending the 2020 season at 8-8.

Gruden's Raiders stole headlines as one of the surprise teams of early 2021, beating the Dolphins in overtime to improve to 3-0 on the year, atop the crowded AFC West. Under his guidance, quarterback Derek Carr seemed to solidify his place as an early MVP candidate.

Four days after falling to the Chargers in prime time for their first loss of the year, the Raiders faced a new dilemma, with the Wall Street Journal reporting that Gruden had used a racial trope to criticize NFLPA executive director DeMaurice Smith in a 2011 email, uncovered as part of a separate workplace investigation into Washington Football Team.

Three days after the Wall Street Journal report, which Gruden downplayed by suggesting he didn't remember sending such criticisms, admitting he also profanely discredited NFL commissioner Roger Goodell and assuring reporters he doesn't have a "blade of racism" despite his old comments going "too far"; The New York Times reported Gruden's emails from 2010-2018

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