Jon Gruden
It’s not just players who sign regrettable contracts; it can happen with coaches too. The Raiders seemed intent on proving that after giving Gruden a 10-year, $100 million contract to return to coaching. However, Gruden’s second stint with the Raiders was filled with controversy and disappointing results.
The Raiders were 4-12 in Gruden’s first season and 15-17 over the next two years. In 2021, the Raiders were 3-2 when Gruden resigned after a series of racist, homophobic, and offensive emails were uncovered. The emails were mean and offensive and targeted several people both inside and outside the NFL. Frankly, it was unlikely that giving Gruden $100 million over 10 years was going to work out for the Raiders. But bringing him back turned out to be far more embarrassing than anybody could have imagined.