4 recent Raiders free agent signings that just didn't pan out

Jon Gruden, Head Coach

Not every bad free agent that is brought in plays on the field.

Ten years and $100 million. That's how much the Raiders were willing to pay for the nostalgia of having Jon Gruden on the sidelines in 2018. And granted, that's maybe not as "recent" as the other ones on this list, but people don't forget.

Some of his first moves included trading Khalil Mack and Amari Cooper, both of who have gone on to have incredibly productive careers elsewhere. In years following, he was fined twice during the 2020 season for violating league pandemic protocols, never won more than eight games – with no playoff appearances – and eventually resigned in Week 5 of the 2021 season after the New York Times released emails from him that included "misogynistic and anti-gay language."

There's a good argument to be made that no free agent signing over the past decade has been worse than this one.

Cory Littleton, LB

After four incredibly productive seasons with the Rams, Littleton signed with the Raiders during the 2020 offseason, inking a three-year, $32 million deal. And then, in two seasons in Vegas, Littleton only registered a half sack (he had 8.5 with the Rams) and never got to 100 tackles, after going over that twice in his previous two seasons.

According to PFF's grades, the two years he was with the Raiders were the worst two of his entire career. His missed tackle percentage skyrocketed – in his last season with the Rams, it was .08 percent; one year later, it was up at 15.4. Since then, he's bounced around the league, making appearances with the Texans and the Panthers.