Oakland Raiders: 15 best free agent acquisitions of all-time

Obviously, this ranking is based upon his time as a player, not a coach, as Rod Woodson has fallen out of favor with Raiders fans in recent times.

Due to some comments after being released from his duties as defensive backs coach and the infamous coin flip with the San Francisco 49ers, Woodson’s name may not be the most popular among the Raider faithful. That aside, Woodson was one of the best defensive backs in Raiders history.

Woodson will be remembered mostly for the incredible 10 years he spent with the Pittsburgh Steelers, his time in Oakland was impressive considering the context. In 2002, the Raiders were loading up for a Super Bowl push, and Woodson happened to be available.

In that offseason, Oakland signed Woodson to a six-year contract. Unfortunately, Woodson only fulfilled two years of that commitment due to injuries.

Regardless of how it ended, Woodson was pivotal in the Raiders’ Super Bowl appearance in 2002. At 37 years old, Woodson earned All-Pro and Pro Bowl honors during that season, as he led the league in interceptions with eight. Playing in the NFL at 37 is impressive enough, let alone starting at free safety and leading the league in interceptions.

The contract is the only bad aspect to this deal. It only looks that way because Woodson injured his knee and was unable to fully recover and failed a physical. Who knows, without the injury, maybe Woodson would go on to play into his 40s?