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15 worst free agent signings in Las Vegas Raiders history

By Brad Weiss

OAKLAND, CA - AUGUST 19: A detailed view of a helmet belonging to and Oakland Raiders player sitting on top of a Gatorade cooler against the Los Angeles Rams during the fourth quarter of their preseason NFL football game at Oakland-Alameda County Coliseum on August 19, 2017 in Oakland, California. The Ram won the game 24-21. (Photo by Thearon W. Henderson/Getty Images)
OAKLAND, CA - AUGUST 19: A detailed view of a helmet belonging to and Oakland Raiders player sitting on top of a Gatorade cooler against the Los Angeles Rams during the fourth quarter of their preseason NFL football game at Oakland-Alameda County Coliseum on August 19, 2017 in Oakland, California. The Ram won the game 24-21. (Photo by Thearon W. Henderson/Getty Images) /
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Raiders Trent Brown
Oct 11, 2020; Kansas City, Missouri, USA; Kansas City Chiefs defensive end Alex Okafor (57) blocks Las Vegas Raiders offensive tackle Trent Brown (77) during the game at Arrowhead Stadium. Mandatory Credit: Denny Medley-USA TODAY Sports /

15 worst free agent signings in Las Vegas Raiders history

No. 13: Trent Brown, Offensive Tackle (4yr-$66M)

With Kolton Miller entrenched as the starting left tackle heading into the 2019 NFL season, Jon Gruden and the front office knew they needed someone on the other side. That led the team to ink Trent Brown to a massive contract, making him the highest-paid offensive tackle in football, after giving him a four-year deal worth $66 million, including $36.75 million guaranteed.

The early returns were outstanding for Brown, as he was a dominant right tackle, giving Derek Carr one of the best tandems at the position in the league. However, it would go sour in a hurry between Brown and the franchise, as he was injured in 2019 and played in only 11 games, then in 2020, a combination of COVID and an error in an IV placement limited him to only five games.

All told, Brown played in only 16 games during his two-year stint with the franchise, eventually being traded with a 2022 seventh-round pick back to New England for a 2022 fifth-round selection. The addition of Brown was supposed to solidify the Raiders’ offensive line for multiple seasons, but instead, his two years with the franchise can only be seen as disappointing, and a real waste of money.

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