Jon Gruden to Reportedly Make $100 Million Over 10 Years as the Oakland Raiders Head Coach Multiple leagues sources have reported that the Raiders will announce Gruden as head coach in a press conference on Tuesday. Gruden previously coached the Raiders from 199-2001 and the Tampa Bay Buccaneers from 2002-2008. Since 2009, Gruen has been the color analyst on Monday Night Football on ESPN. Saturday's wild-card between Tennessee and Kansas City will be his final game in the booth.