The Raiders' second-year coach had already clashed with the quarterback he inherited in Jeff George, so Jon Gruden needed someone who could implement his version of the West Coast offense in 1999. Paging Gannon, who was the epitome of a journeyman quarterback who simply needed a fresh start, and for a coach to believe in him enough to give him the reins.
It turned out to be a symbiotic relationship that would define the most successful era yet of the Raiders' return from Los Angeles.
With Gannon, who was a fourth-round draft pick of the New England Patriots in 1987 before spending time in Minnesota, Washington and Kansas City, the Raiders won AFC West titles in 2000, 2001 and 2002. He made four Pro Bowl appearances wearing an Oakland uniform. Even after Gruden was traded to Tampa Bay following the 2001 season, Gannon responded with his best season as he joined Ken Stabler (1974) and Marcus Allen (1985) as the only Raiders to be named NFL MVP.
In 2002, Gannon passed for a franchise-record 4,689 yards with 26 touchdowns, 10 interceptions and a career-best 67.6 percent completion rate. His 418 completions set a league record.
But the Lombardi Trophy eluded Gannon as the Raiders faced Gruden and the Buccaneers in Super Bowl XXXVII, and Gruden knew Gannon better than Gannon knew himself. Gannon threw a Super Bowl-record five interceptions, including three pick-6's, and the Raiders were thumped, 48-21.
Gannon was limited to just 10 games over the next two seasons. A broken vertebrae in his neck suffered in Week 3 of the 2004 season -- thanks to a helmet-to-helmet blow with the Buccaneers' Derrick Brooks -- effectively ended his career.