Charles Woodson, CB
I don't care what anyone has to say about Charles Woodson leaving to go sign with the Packers and that move ultimately revitalizing his career. If you're a Raiders fan, you're likely still bitter that he went on and made another four Pro Bowls and two All Pro selections in Green Bay.
Woodson spent the first eight years of his career with Oakland, and his career started with a bang. Woodson made four Pro Bowls in a row to begin his career, and also finished with an All Pro nod in addition to winning Defensive Rookie of the Year back in 1998.
His last year with the Raiders was shortened due to injury, but the Raiders ultimately decided to see him go sign elsewhere instead of fighting to keep a legend at home. It was a great move for Woodson, who went on to see a ton of success with the Packers, including a Super Bowl victory during the 2011 season.
But, as for how it stung for Raiders fans to watch all of that unfold? It was tough. He belonged in Oakland, period. The only saving grace was to see Woodson come back and finish his career in the silver and black.