A look at the Raiders’ worst signings, including Christian Wilkins

The surprise release of defensive tackle Christian Wilkins on Thursday led many Raiders fans to invoke the name of former wide receiver Javon Walker.

The message wasn’t a positive one.

Wilkins has taken his place on a list most commonly topped by Walker as the worst free-agent signing in franchise history after playing in just five games on a four-year, $110 million contract he signed in 2024.

Walker signed a six-year, $55 million contract with the Raiders in 2008. He caught 15 passes in eight games in his first season in Oakland before getting injured. He then failed to catch a pass in three games in 2009 before he was released.

He collected $21 million for his efforts, a large amount at the time.

Wilkins’ tenure might be even more disappointing. He recorded only two sacks in those five games before he was released 16 months after signing his contract.

But those deals aren’t alone in a checkered history of questionable Raiders free-agent signings.

Las Vegas era

Since the Raiders moved to Las Vegas from Oakland in 2020, none of the four largest contracts they have doled out for outside players looks great in retrospect.

Quarterback Jimmy Garoppolo got $72.75 million for three years and lasted one season before he was released.

Edge rusher Chandler Jones got $51 million for three years and was also released after one largely ineffective season that was followed by a tumultuous offseason that included multiple arrests.

Linebacker Cory Littleton lasted two years on a three-year, $35 million contract, though his tenure probably should be seen as a rousing success compared to the others. He played in 31 games and had 180 total tackles.

Worst deals ever?

Of course, the Raiders’ history dates much further than their move to Las Vegas, and there were plenty of bad deals done in Oakland during the era of free agency that dates to 1993.

Two of them even made an nfl.com list of worst free-agency signings in league history.

The Raiders signed former Cowboys defensive back Larry Brown after he was named Super Bowl MVP with Dallas in 1996.

But he didn’t parlay that great performance on the game’s biggest stage as a springboard to success in Oakland. Actually, he barely got on the field.

Brown played in just 12 games — starting one — in two years after signing a five-year contract. His tenure included a suspension for conduct detrimental to the team.

Yet it wasn’t enough to dissuade the Raiders from signing the Super Bowl MVP the following season, when they gave Desmond Howard a four-year deal after he became the only player to win the award solely by playing on special teams.

Howard was OK for the Raiders, particularly as a kick returner, where he led the league in yardage. But he was pedestrian as a punt returner and almost nonexistent as a pass catcher despite making top receiver money. He lasted two seasons.

The list goes on and on.

Quarterback Aaron Brooks got two years and $9 million but played only one year, going 0-8 as a starter as part of a 2-14 record that put the Raiders in a position to draft JaMarcus Russell. Brooks never played again.

From bad to bizarre

The reasons for which deals have gone south are varied and, in some cases, odd.

Vontaze Burfict arrived in 2019 with a reputation as a big hitter who toed the line of the rule book, which proved to be his downfall when he was suspended for the rest of the season after four games.

Cornerback Sean Smith finished two years of a four-year contract. His career ended then when he pleaded guilty to felony assault against his sister’s boyfriend.

Then there was safety Gibril Wilson, who lasted one year of a six-year deal in 2008. Almost hilariously, the Dolphins immediately signed him to a five-year deal, and he played one season in Miami. He’s considered one of the worst free-agent signings in Dolphins history, too.

Linebacker LaMarr Woodley signed as a pass rush specialist in 2014, but didn’t record a sack before being released.

Safety LaMarcus Joyner was signed in 2019 to cover slot receivers, but didn’t have an interception in the two years he lasted on his four-year contract.

Another cornerback, Ray Buchanan, suffered a similar fate. “Big Play Ray” had one interception in 16 games for the Raiders after picking off 47 in his first 11 seasons. He was cut one year into a five-year deal.

Mentioning names such as Tyrell Williams, Tahir Whitehead, Kwame Harris and Shawntae Spencer just feels like piling on at this point.

But before jumping to the conclusion that signing free agents isn’t the best way to build a team, it should be noted that trades aren’t a sure route, either.

Perhaps the worst big-time acquisition in team history was wide receiver Antonio Brown, who never played a game for the Raiders after they gave up two draft picks for him and signed him to a new contract.

Another star wide receiver, Davante Adams, was productive after he was acquired in a trade. But a lack of wins and frustration over the direction of the organization soon led to a divorce between the Raiders and Adams.

So, Wilkins has plenty of history in the story of the franchise’s biggest swings and misses.

Contact Adam Hill at ahill@reviewjournal.com. Follow @AdamHillLVRJ on X.