Jan 6, 2001; Oakland, CA, USA; Oakland Raiders quarterback Rich Gannon (12) and Raider headcoach Jon Gruden converse during a 2nd quarter timeout as the Oakland Raiders defeated the Miami Dolphins 27-0 advancing to the AFC championship game for the first time since 1991. Mandatory Credit: Jack Gruber-USA Today Jack Gruber-Imagn Images

Report: Rich Gannon Was One of the Best Free Agency Deals Ever

Originally posted on Las Vegas Raiders on SI
By Ezekiel Trezevant | Last updated Feb 7, 2025 12:30 PM ET

The Las Vegas Raiders have a storied history, filled with some of the most notable players, coaches and happenings in National Football League history.

The Raiders' history spans many decades and contains many successful seasons.

Some of the most well-known players in league history played up Silver and Black.

Sterling Xie of the Pro Football Network recently ranked the best free agent signings of all time. He ranked Gannon signing with the Raiders in 1999 as the 11th-best free agency signing in NFL history, as Gannon would finish his career as one of the all-time leading passer in Raiders' history.

Xie noted that Gannon that while Gannon found success everywhere he went, it was his time with the Raiders that Gannon became a household name under former Raiders head coach Jon Gruden.

"After 11 NFL seasons with three franchises, there was seemingly no mystery left to Rich Gannon’s career," Xie said. "After all, he had never made the Pro Bowl, passed for 3,000 yards, or started a playoff game. It was a solid career for the former fourth-round pick, but there was little reason to believe that Gannon was anything more than a low-level starter or high-end backup.

"That changed when he left the Kansas City Chiefs for the AFC West rival Oakland Raiders in 1999. Gannon thrived under Jon Gruden, earning four straight Pro Bowl appearances from 1999-2002. The last of those seasons was his peak, as Gannon won MVP at age 37 with an NFL-high 4,689 passing yards."

Xie noted that although Gannon lost in the Super Bowl, Gannon still had a respectable career overall. Although Gannon's career ended shortly after, his time with the Raiders is remembered favorably.

"The season ended on an extremely sour note for Gannon and the Raiders, who were soundly dominated by Gruden’s new team, the Tampa Bay Buccaneers, in Super Bowl 37," Xie said. "That essentially marked the end of Gannon’s terrific run, as he suffered a serious shoulder injury after seven games in 2003 and only played three more games the rest of his career.

"Still, Gannon’s shocking late-career surge provided the most recent taste of glory for a formerly proud franchise. The Raiders have not won a playoff game since the 2002 AFC Championship Game, as Gannon’s arrival made Oakland’s brief window of contention possible."

This article first appeared on Las Vegas Raiders on SI and was syndicated with permission.

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