The 36-year-old veteran, taking over for good friend Trent Williams, maybe for good, isn’t taking anything for granted even after coach Jay Gruden confirmed Monday he would be the starter in Week 1 against the Philadelphia Eagles on Sept. 8. 

“I’m not there yet,” Penn said. “I’m still working. I’m still trying to get there. I’m almost there, but I ain’t there yet so I’m not going to give you all the cheese.”

The Williams saga shows no signs of abating. He remains away from Redskins Park with the season less than two weeks away now. Gruden again said Monday that he believes the team will not trade Williams, a seven-time Pro Bowl left tackle who is holding out in large part because of a fractured relationship with the team’s front office and medical staff – or maybe just because he wants more money. 

Depends on who you want to believe in this game of chicken that leaves Washington in a tough position. Penn, entering his 14thNFL season, a durable, effective starter for over a decade with Tampa Bay and then Oakland, is tasked with filling Williams’ giant shoes. 

Gruden responded like a man headed for dental surgery when asked for an update on Williams and to reaffirm his belief he won’t be traded. This can’t be easy on him.

“Yes, I still feel that way. Very strongly, yes,” Gruden said, pausing almost between every word. 


For his part, Penn talked with Williams about his status last month and then signed with Washington on July 31. He’s put in almost a month of work now and feels more comfortable. Last year, his final one in Oakland, he never did after getting moved to right tackle by the coaching staff and then going on IR after four games with a groin injury. The Raiders released him in March. Now, Penn knows he will start for Washington against the Eagles. 

“[Penn is] an older guy, but his legs are starting to get under him right now,” Gruden said. “He's in decent shape for an old, ugly body guy. But he's done a pretty good job. He's seen a lot of football, played a lot of football; he knows how to set on these guys. He's not quite where he was when he was 22 years old, but he's still a very functional left tackle in the NFL.”

Penn has been in Williams’ position before. He held out in 2017 because he wanted to be paid like one of the top 10 tackles in the NFL. He didn’t report to Oakland until Aug. 23 that summer and the two sides eventually worked out a two-year, $20.6 million extension. 

But he also acknowledged that Williams’ holdout is far more personal. Either way, the uncertainty weighs on a player until a resolution, any resolution, comes.   

“Not knowing….It’s a little frustrating, a little stressing. I know that feeling,” Penn said. “A lot of guys you want to know. Hey, I don’t what Trent’s thinking, I don’t know what his mind is made up, I don’t know his thoughts. I know what we talked about a couple weeks ago and that’s it. Things could have changed since then.”