After a decade of horrible left tackle play, the Buccaneers seem to have finally found their man. Donald Penn is the first Buccaneers tackle to earn a long-term, expensive deal since Paul Gruber. And while Donald Penn's play wasn't superb last season, it was pretty good, and the Pro Bowl alternate earned his money. Donald Penn isn't going anywhere, so there's little point to discussing the left tackle position.
The right tackle position, though, is another matter entirely. Jeremy Trueblood is scheduled to be an unrestricted free agent under expected CBA rules, and his replacement James Lee is a restricted free agent who has been tendered. Trueblood has been the weak link on the offensive line for years now as a pass blocker, and should only be back as a backup or to offer competition. James Lee showed himself to be competent as a pass blocker, though he could be improved upon pretty easily as well. That's where the Bucs have plenty of work to do.
Doug Free is probably the best of the bunch, but it seems likely that the Cowboys will re-sign him. Willie Colon is in a similar position for the Steelers, although missing last year with a hamstring injury may lead the Steelers to let him go. Jared Gaither is an interesting player who has maintained a relatively high level of play, but whose career has been slowed down by injuries. If he can get over the injuries he would be a very good right tackle. Brown was a very good player for the Saints but has lost a lot in recent years and is no longer a competent pass blocker. Jermon Bushrod replaced Brown but was hardly better, as the tackle was the weak point of the Saints' offensive line, being especially weak in pass protection.
Matt Light is an intriguing option as the Patriot is still playing at a high level, but at 33 years he is likely too old for the Bucs to seriously consider him. The most intriguing option may be Atlanta Falcon Tyson Clabo, a solid and workmanlike tackle who excels at nothing but is decent at everything. At 29 he is older, but likely still has multiple years of good play ahead of him. He may demand the most money on the free agency market, though.
If the Bucs do not sign any free agents, they will have to rely on the young backups they've collected. Of those players, Demar Dotson is the most intriguing player. He played basketball in college but has an immense amount of physical talent to play offensive tackle. Unfortunately, he has never seen the field for the Bucs due to inexperience and injury, and he will have to fight hard to make the roster next season. The other prominent backup on the roster is Will Barker, an undrafted rookie in 2010. He spent most of last season on the roster, albeit as an inactive player. He is basically an unknown, but he could show something in camp.
In the end, I think we'll still see Donald Penn and James Lee starting for the Bucs next season, but I also expect a free agent to be brought in to bolster the group and provide some competition. That player could be Jeremy Trueblood, but it could also be one of the offensive tackles I mentioned before. If someone like Jared Gaither or Tyson Clabo signs, expect them to start at right tackle instead of James Lee.