Oakland Raiders: Best free agent moves of the Reggie McKenzie era

Donald Penn (2014)

When McKenzie set out to upgrade the offensive line, his first move was one of his best. When the Tampa Bay Buccaneers cut Penn loose, McKenzie was quick to pounce, bringing him to Oakland on a two-year, $9.6 million deal.

It’s turned out to be one of McKenzie’s best moves in free agency over his tenure.

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Since his signing, Penn has been named to two Pro Bowls (2016, 2017), and has been one of the most dominant left tackles in football. Although on the wrong side of 30, Penn has been dominant at his position, allowing very few defenders to get their hands on quarterback Derek Carr.

In 2016, Penn signed a two-year deal worth $14 million dollars, but ahead of the 2017 season, held out for a new contract that paid him like the top-ten tackle he’s been over his time in Oakland.

Eventually, the tense standoff ended with the Raiders giving Penn a new two-year, $21 million dollar deal.

This year, Penn is going to be reunited with Gruden, whom he played for in Tampa for a few seasons. Though, with Penn set to turn 35 this year, and the team incurring no dead cap money if they cut him after this season, it could be his final year in Silver and Black.

Unless, of course, he continues to defy Father Time and plays at an elite level – which is possible. Don’t ever count Donald Penn out.

Either way, the addition of Penn, and the skill and attitude he brought to Oakland’s line has to be considered one of McKenzie’s best free agent signings.