Along with Lee Roy Selmon and teammate Derrick Brooks, Sapp is one of three players to have his number retired by the Buccaneers.

Many top nationally ranked college football programs recruited Sapp and he played at the University of Miami for the Hurricanes, where he was a defensive standout.

Sapp was considered a potential top five or 10 pick, but due to reports of multiple failed cocaine and marijuana tests released the night before the draft, many teams passed on him.

[10] The NFL released a statement strongly denying the rumors and Sapp believed an anonymous individual attempted to intentionally sabotage his draft chances.

On November 24, 2002, at Raymond James Stadium, Sapp was strongly criticized for a blindside hit on the Green Bay Packers' Chad Clifton.

In 2005, the NFL Competition Committee agreed on new guidelines for "unnecessary roughness", making hits such as Sapp's on Clifton illegal.

In an exchange caught by television cameras following the game, Packers coach Mike Sherman approached Sapp and said to him, "That was a chickenshit play.

"[13] Sherman later added, "The joviality that existed after [the hit] when a guy's lying on the ground, with numbness in his legs and fingers, I just thought that wasn't appropriate for any NFL player.

"[14] During pregame warmups for the December 23, 2002 Monday Night Football game at Raymond James Stadium, Sapp skipped among the Pittsburgh Steelers as they warmed up.

The Colts wound up erasing a 21-point deficit in the final four minutes and defeating the Buccaneers 38–35 in overtime, sending the defending champions into a downslide.

The next Sunday, October 12, 2003, before the Buccaneers took on the Washington Redskins, Sapp, while running onto the field, bumped into an NFL referee and drew a $50,000 fine.

[18] The incident began when linesman Jerry Bergman mistakenly assumed that the Raiders would decline a ten-yard Jaguar penalty.

Sapp, the defensive captain, shot back at referee Jerome Boger, that the Raiders wanted to accept the penalty.

[19] On January 3, 2008, Sapp told Raider owner Al Davis over the phone that he would retire[20] and confirmed this on his website qbkilla.com in just two words: "I'M DONE!

Michael Strahan, James Harrison, Ed Reed, Troy Polamalu, Charles Woodson, Terrell Suggs, Stephon Gilmore, and Aaron Donald have since joined the list.

[25] Sapp, Devin Bush and a developer created an Urban Solutions Group in 2006 to construct low-income housing in Fort Pierce, Florida.

The PNC Bank loaned the group money, but by 2008 the real estate market tanked and the project ended in failure.

[27] Sapp's partner for the competition was professional dancer Kym Johnson; the pair made it to the finals where they were eventually named runner-up of season 7.

[31] In January 2013, Sapp worked with Dr. Jonathan Greenburg to raise awareness about the importance of getting tested and treated for snoring and obstructive sleep apnea.

Sapp and Jones have interviewed celebrities such as Derrick Johnson, Adam Schefter, Ray Lewis, Kevin Carter, Rick Neuheisel, and Jen Welter on the podcast.

[38] In 2010, PNC Bank was awarded a judgment of $988,691.99, and in December 2011 filed a monthly lien of $33,333 against Sapp's $45,000 NFL Network paycheck.

[4] On April 7, 2012, the Associated Press reported that Sapp had filed for bankruptcy in an effort to discharge debt from failed businesses.

He claimed no credit card debt and owns no automobiles, but owes National Car Rental $90,685 through his business, Nine-Nine LLC.