Trent Williams okay with Redskins signing Donald Penn

The Washington Redskins are in a tenuous position with their offensive line in 2019. Their future Hall-of-Fame left tackle, Trent Williams, is in the midst a holdout and resolving it will be more difficult than most contractual disagreements. The larger issue of what caused the holdout in the first place (an egregious medical mishap) is a daunting one and resolving it will be what drives the result.

Enter now veteran left tackle Donald Penn, who the Redskins signed yesterday to a one-year contract. The 13-year veteran is a proven talent who entered the league in 2006 as an undrafted college free agent (brought in by the Minnesota Vikings). In 2007, he went to Tampa to play with the Buccaneers and spent the next seven seasons in Florida, earning a Pro Bowl berth in 2010 as well as a spot on the NFL’s Top 100 roster in 2012. In 2014, Penn was signed by the Oakland Raiders where he played until last season, landing two more Pro Bowl appearances in 2016 and 2017.

The move to bring Penn on makes sense in the wake of uncertainty surrounding Williams considering the team has two new quarterbacks, one of which is a rookie. But most interesting is that Penn and Williams are friends and the former Raider said that he had spoken to his fellow left tackle before deciding to come to the nation’s capital. And according to Penn, Williams was fine with the team bringing him in to possibly start in his place.

“Trent’s one of my good friends,” Penn said today in a post-practice press conference. “I reached out to Trent before I signed and we had a good conversation. We talked and we’re on the same page.

“I’m not going to get into that too much,” he continued when asked what was said during the discussion. “It was a personal conversation between me and Trent but I’ll just leave it at that.”

On a light note, Penn has said more than once that he was comfortable signing with Washington because he will be so comfortable in Jay Gruden’s offensive system. And this makes sense. After all, the former Aggie played for Gruden’s older brother successfully from 2014 to 2018 and the two coaches have similar systems and offensive philosophies.

“It’s funny too because [Jon] Gruden texted me, talking about, ‘you can’t shake the Grudens,’ Penn said. “[He’s] joking, but I grew up a Raider fan so it was like a dream come true, you know, playing for a team I grew up in. I did a lot of special things there, I have a lot of some special friends there. I was playing and thought I was going to retire a Raider but it didn’t happen like that. I’m always going to love my time there; I’m always going to love the Raiders. But now I’m Redskin. I’m ready for this new chapter and I’m happy and especially happy to be back at left tackle because I feel so much more comfortable.”