Gruden attended Lions camp to support new Detroit offensive coordinator John Morton, whose first coaching job came as an assistant under Gruden with the Oakland Raiders in the late 1990s. He later worked for Gruden again during his second stint leading the Raiders in Oakland and later Las Vegas, before his resignation.

The last head coaching job that Jon Gruden took over was with the Las Vegas Raiders. He served them from 2018 to 2021 before becoming an employee for Barstool Sports.