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

Donald Penn is the first of several offensive linemen to make this list. Apparently, the Raiders have a knack for signing offensive linemen in free agency.

After making his name with the Tampa Bay Buccaneers, Penn decided to remain a pirate, signing with the Raiders in 2014. His original deal was for two years and $9.6 million, yet the tackle remains on the roster in 2019. Obviously, the deal worked out for both sides.

From day one with Oakland, Penn was the starting left tackle. For the first three seasons as a Raider, Penn didn’t miss a single game, starting in all of them.

Unfortunately, Penn missed the Raiders’ lone playoff game during that stretch after the 12-4 regular season in 2016. At the time, Penn was one of the longest tenured NFL players to have not played in a playoff game.

After 2016, Penn signed a contract extension for two more seasons and $14 million, that would later be upped to $21 million after a brief holdout after the 2017 season.

After Kolton Miller’s selection in the 2018 NFL Draft, Penn lost his spot starting at left tackle. Showing his versatility, Penn moved to the right side, but due to injury, he only played in four games in 2018, opening the door for Brandon Parker to fill his place.

Whether or not Penn returns to the starting lineup in 2019, his time in Silver and Black was great. He earned Pro Bowl honors twice during his stay in 2016 and 2017. Penn was a huge part of an offensive line that was deemed top-three in the NFL during that period.