6. Donald Penn
After going undrafted, Donald Penn put together an impressive 13-year career that exceeded all expectations. He signed with the Raiders in 2014 and would go on to make the Pro Bowl twice before an injury-plagued 2018 season ended his tenure with the team.
The 2016 season was the peak of the big man’s career as the offensive line allowed a league-low 18 sacks and the team rushed for 1,922 yards, the sixth-most in the NFL. That season, the Raiders went to the playoffs for the first time since 2002, though it was a sack allowed by Penn that ended up breaking Derek Carr’s leg.
His two receiving touchdowns also add to Penn’s pedigree with Oakland. He will go down as one of the organization’s best offensive linemen in the era. While he was eventually replaced by Kolton Miller as the man protecting Derek Carr’s blindside, nobody has done it better since Carr entered the league in 2014.