With the commencement of the free agency craze, the Tampa Bay Buccaneers brought back a familiar face to solidify the secondary. Whitehead, who the Bucs selected in the fourth round of the 2018 NFL Draft, signed a two-year deal with Tampa Bay after spending the previous two seasons with the New York Jets.

In his first four campaigns with the Buccaneers, Whitehead tallied 292 tackles, five interceptions, 25 passes defensed, 2.0 sacks and 22 tackles for loss in 59 games. In six playoff games, Whitehead posted another 22 tackles, a pass defensed and two forced fumbles. In the 2020 NFC Championship Game, Whitehead spurred the team's victory at Lambeau Field. He forced an Aaron Jones fumble in Green Bay territory to start the second half, which led to a touchdown for the Bucs and subsequent 28-10 advantage.

While with the Jets, Whitehead played in and started all 34 of the team's games. His 321 and 286 snaps in pass coverage in 2022 and 2023 were the two highest totals of his career (blitzed 1%). Whitehead amassed 186 tackles during that span along with six interceptions and 17 passes defensed, including career-highs in interceptions (four) and tackles (97) in 2023. That stint with the Jets fostered growth and enhanced his craft. Whitehead had built a reputation as the prototypical hard-hitting, box safety. In New York, Whitehead was not just utilized on run downs and showcased his range and pass coverage abilities while manning the middle of the field.

"What I did learn was a different scheme, a different defense, so I had to adjust," Whitehead described on his time with the Jets. "It brought out another game in me that some people didn't know I had – or even myself. I knew it was there, but I just needed to show it. We sat back in a lot of Cover Four with the Jets. I was in the pass game a lot and didn't really have any blitzes. I sat back in pass [coverage].  I was going against Aaron Rodgers everyday in [training] camp and that brought another level out of me. I'd say my game elevated just from being in a pass defense, learning to read coverages, learning to read the offenses, reading the quarterback out of the middle of the field. There was just certain stuff that I didn't get to do as much here because I was in the box so much. I was always labeled as a box safety, but my label now wouldn't say that because I feel comfortable playing man-to-man, playing in the post. I wouldn't say I prefer it, but it's always good to sit back and get interceptions and not just be a big hitter. I'm just two years older now, I'm smarter, wiser. I go home and watch film with the coaches and it's a part of my game that I love. You don't just have to be physical, there's a lot of mental stuff there."

With an expanded role for New York, Whitehead placed an emphasis on mental fortitude and film study, which paid dividends on the field. For the Bucs in 2023, Winfield Jr. reverted back to his role at free safety and several players rotated in the strong safety spot including Ryan Neal, Dee Delaney, Zyon McCollum and Kaevon Merriweather. The Bucs predominately lined up in zone coverage last season (450 snaps). Additionally, Tampa Bay lined up with a single-high safety on 338 snaps and with split safeties (Cover Two) on 250 snaps. The Bucs were in man on 161 snaps and Whitehead's versatility will elevate the back end in 2024. Both Whitehead and Winfield Jr. will likely form a tandem once again in the Bucs' backfield come fall, fortifying the club's last line of defense.

Whitehead, an athletic chess piece, has a knack for forcing fumbles and possesses stellar closing speed. The former Pitt playmaker is adept at shooting gaps with short-area burst and pursuing ball carriers across the field. Whitehead is a fearless downhill tackler, delivering earth-shattering hits to jar the ball loose. The heat-seeking missile effectively navigates through traffic to get to rushers before the cutback. He displays a rare gear in getting from Point A to Point B on the field, much like his counterpart, Winfield Jr. Whitehead has the coverage tools to match up with slot receivers and tight ends down the seams, which will make him an asset in Todd Bowles' exotic defense.

"Playing for Coach [Todd] Bowles…I don't know what player wouldn't want to play for him, especially being a defense player, being a safety, linebacker, cornerback – if you're one of those positions, he's going to put you in the best possible situations," stated Whitehead. "He's going to bring the best out of your game. The person he is – you can talk about anything with him, from ball to life. That's the biggest thing coming around [for] my second time. I got in his office, and we sat up there for an hour. The first 10 minutes you talk about football then after that you just talk about life. I can't say [anything] wrong about Coach [Todd] Bowles. He's been there for me ever since I came [into the league]. He's been coaching me. Him bringing me back here, that says enough right there, giving me an opportunity."

Whitehead plays the game the way it should be played. With contagious energy and a competitive disposition on the gridiron, he sets the tone. Whitehead possesses the traits that Bowles' covets and the well-rounded safety will galvanize the squad in 2024.