Penn became a premier blindside protector during his time in Oakland, anchoring an offensive line that, for a time, rated as arguably the best in the NFL. The Raiders signed Penn in 2014 after the Tampa Bay Buccaneers allowed him to depart in free agency. The move proved to be a masterstroke by then-general manager Reggie McKenzie. Penn started all but two games over the next four years, allowing just 16 sacks over that stretch and helping the Raiders end a 14-year playoff drought. For his efforts, he earned multiple Pro Bowl nods and two-year, $18.7 million contract in 2017.
However, with the arrival of head coach Jon Gruden, Penn saw his role in the offense shift. Gruden installed 2018 first-round pick Kolton Miller at left tackle and shifted Penn over to the right side. A groin injury ended Penn's season after four games, the first prolonged absence of the offensive lineman's 12-year career.
"We're going to miss Donald Penn around here," Gruden said in a team statement. "I got to coach him as a young guy in Tampa and everything he got on the field, he earned. I was lucky enough to get him again here in Oakland. I'm going to miss the toughness and passion that he brought to the team every day. I certainly wish him and his family all the best."
"It has been an incredible chapter. These past five years have been some of the greatest of my life and I will cherish the memories for a lifetime," Penn said on social media, adding, "This game is a crazy journey, but I love it unconditionally. Looking forward to the next chapter of my career -- I've got a lot of football LEFT!"