Oakland Raiders: Top-20 players of the 21st Century

Donald Penn (2014-2018)

Donald Penn was not the biggest prospect when he arrived in the NFL, being signed by the Washington Redskins as an undrafted rookie free agent. However, he worked his way into being one of the premier left tackles in the game for the Oakland Raiders, where he served as the man protecting Derek Carr’s blindside early in the quarterback’s career.

In fact, Penn was absolutely dominant in protecting Carr, as he rarely allowed the young signal-caller to be touched. A  two-time Pro Bowler during his time with the Silver and Black, Penn would see his run with the team end last season, as injuries, and a youth movement along the offensive line proved to be his downfall in Oakland.

Still, Penn was a mauler for the Raiders, and helped this team become one of the better overall units in the NFL during the 2016 NFL season. With the team drafting Kolton Miller in the first round in 2018, and the signing of Trent Brown this offseason, there was no room for him on the roster for the 2019 campaign, but when he was right, he was one of the better left tackles in football.