Jon Gruden had an up-and-down tenure during his second time leading the Las Vegas Raiders. While he was at the helm as the franchise moved from Oakland to Las Vegas and the franchise's record improved in each of his four seasons, the lone winning campaign came in 2021 after he was fired.
The Raiders were just 22-31 during his stint, failing to reach the postseason in that span. It was recently revealed that, despite the lack of success under Gruden, the head coach passed on an opportunity to bring in Tom Brady following his departure from the New England Patriots.