While he wasn’t actually a player for the Buccaneers, head coach Tony Dungy is the second most deserving former Buccaneer that should have won a Super Bowl.
Dungy was heavily instrumental in putting together the 2002/2003 Buccaneer team that won the Super Bowl for fans who are unfamiliar with that team. Dungy experienced a high level of success with the Bucs from 1996 until the end of the 2001 season.
Despite going 54 and 42 during this time (well above .500) and winning the NFC Central back in 1999, the Bucs moved on from Dungy after the 2001 season, even though Tampa Bay had a winning record.
That next year, Jon Gruden was hired as the head coach of the Bucs and the team won a Super Bowl.
Dungy was really the architect behind that Super Bowl win, and the effort he put into the team through various drafts and free agency played a significant role in giving Tampa Bay its first and only title.
He may have eventually won a ring later in his career, but Dungy is as deserving as any former Buccaneer for a Super Bowl ring with Tampa Bay, especially when looking at the work he did laying the foundations for the Bucs to become relevant for one of the longest periods in franchise history.