Donald Penn, OT, Oakland Raiders: Then-Bucs coach Jon Gruden signed Penn as an undrafted free agent more than a decade ago. It would be on brand for Gruden, who was quietly ruthless with personnel decisions in Tampa, to make letting go of Penn one of his first big moves in Oakland. The drafting of Kolton Miller in the first round was the first ominous sign. Gruden's decision to keep Miller at left tackle during offseason practices, rather than moving him to the right side, was another one. While Gruden has insisted the arrival of Miller has nothing to do with Penn, the 35-year-old is coming off Lisfranc foot surgery. The guaranteed money in his contract ($3 million of his $6 million base salary) should help Penn make the team, but he has to prove he's healthy first.