After 17 years away from the Raiders organization, Jon Gruden returned to the fold in the January of 2018, taking over for Jack Del Rio, who led the Raiders to their first playoff appearance since 2003 in 2016. Gruden inherited a broken roster with big contracts, and sub par players, and quickly got to work breaking it all down.
Of course, he made some moves that irked Raider Nation, including trading away Khalil Mack, who was a generational talent that the team drafted in 2014. In exchange for Mack, Gruden got two first round draft picks among other assets, and he then added another first round pick by trading away Amari Cooper during the 2018 campaign.