Number 8: Donald Penn – T (2007-2013)
Donald Penn entered the NFL the hard way. The Minnesota Vikings signed him and an undrafted free agent out of Utah State in 2006, but he wouldn’t actually see the field until being signed by the Buccaneers the next season in 2007. It ended up being the Buccaneers bargain of the decade.
Penn started in 12 games his first season in Tampa but appeared in all 16. Once he got the starting job, he never relinquished it until he was let go in 2013 in favor of Anthony Collins (we covered that snafu in our worst free-agent signings list and won’t poison this one with all of those details). This mountain of a man was a stalwart at left tackle, playing in 112 games, and making it to a Pro Bowl in 2010. That offseason, he was rewarded with a six-year, $48 million contract extension.
While the way he exited may not have been the most fitting, Penn was, and remains, a fan-favorite. The 315-pound Penn’s reliable play, coupled with his two touchdown catches with the Buccaneers, certainly helped that as well. This was an absolute heist of epic proportions for the Buccaneers, and deserving of a spot on the list.