Does Kenny Pickett Trade Make Raiders Minority Owner Tom Brady Have to Eat His Words

The Las Vegas Raiders traded for quarterback Kenny Pickett earlier this week. In his rookie season, he squared off against now Raiders minority owner Tom Brady, and Brady had an interesting take on it.

Tom Brady appears at American Dream for the grand opening of Card Vault by Tom Brady, a sports card and memorabilia retailer, East Rutherford, Friday, Apr. 11, 2025. | Anne-Marie Caruso/NorthJersey.com / USA TODAY NETWORK via Imagn Images

When it comes to the Las Vegas Raiders picking their quarterbacks now, they have the best quarterback in National Football League history to lean on. Raiders minority owner Tom Brady is now in the middle of making some tough decisions for the organization. It all started this offseason when the Raiders had to make sure they got a better quarterback. Brady was in the middle of the Raiders, bringing in Geno Smith this offseason.

The Raiders had another decision to make on a quarterback earlier this week as well. After backup quarterback Aidan O'Connell went down in the team's last preseason game with an injury. The Raiders were in search of a new backup quarterback. The Raiders sent out and traded for former first-round pick Kenny Pickett. The Raiders made that trade with the Cleveland Browns.

What makes things interesting is the fact that Tom Brady and Kenny Pickett have crossed paths before. In Brady's final season, while he was the quarterback for the Tampa Bay Buccaneers, Brady faced off against a rookie quarterback in Pickett, who was playing for the Pittsburgh Steelers.

Tom Brady & Kenny Pickett

In that matchup in 2022, the Steelers were getting the best of Brady and the Bucs. With a 10-6 lead for the Steelers, in the 2nd quarter, Brady grew frustrated with what was happening on the field just before halftime.

Tampa Bay Buccaneers quarterback Tom Brady (12) throws the ball against the Arizona Cardinals at State Farm Stadium in Glendale on Dec. 25, 2022. | Joe Rondone/The Republic / USA TODAY NETWORK via Imagn Images

“I didn’t leave my wife and kids to be losing to Kenny ... Pickett at the half,” said Brady during that matchup against Pickett in 2022.

That message that Brady said that day, did not work. Brady and the Bucs went on to lose to Pickett and the Steelers 20-18. It was a moment now the two could possibly talk about if they run into each other with them both now being members of the Raiders franchise.

Jun 12, 2025; Berea, OH, USA; Cleveland Browns quarterback Kenny Pickett (8) looks on during mini camp at CrossCountry Mortgage Campus. Mandatory Credit: Ken Blaze-Imagn Images | Ken Blaze-Imagn Images

As for Pickett, he will now come in and backup Geno Smith. Pickett will have to learn the Chip Kelly offense and get up to speed with his new teammates. Pickett has started games in the NFL and knows what it takes to be a serviceable quarterback in the NFL. The Raiders like that he has started in games and has a skill set that they were looking for in a backup quarterback.

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