Caldwell enters the second season of his second stint with Tampa Bay in 2026, marking his fifth total season as inside linebackers coach for the Buccaneers.
In his return to Tampa Bay in 2025, Caldwell coached veteran linebacker Lavonte David to yet another 100-tackle season on the way to tying Pro Football Hall of Famer Derrick Brooks for the franchise's all-time tackles record (1,714). In addition to his team-high 114 tackles (eight for loss), David added 3.5 sacks, three passes defensed, two forced fumbles, two fumble recoveries and one interception. Dating back to at least 2000, David joined London Fletcher (2012) as the only players 35-or-older to record a season with 100+ tackles, three-plus sacks and three-plus takeaways. David's counterpart, SirVocea Dennis, also eclipsed 100 tackles in 2025, setting career highs in tackles (100), tackles for loss (10), quarterback hits (seven), passes defensed (five), sacks (3.0) and interceptions (one). David and Dennis were 1-of-2 duos across the league in 2025 in which both inside linebackers notched 100+ tackles and three-or-more sacks.
Prior to returning to Tampa Bay, Caldwell most recently worked as the run game coordinator/linebackers coach for the Las Vegas Raiders in 2024, following a two-year stint with the Jacksonville Jaguars as defensive coordinator (2022-23). In 2022, the Jaguars defense finished first in the NFL in passes defensed (95) and tied for fourth in takeaways (27) under Caldwell's guidance.
Prior to Jacksonville, Caldwell spent the previous three seasons with the Buccaneers (2019-21) as inside linebackers coach, where he coached Lavonte David to second-team All-Pro recognition and Devin White to both Pro Bowl and second-team All-Pro honors during that span. During his three seasons in this role, Caldwell instructed a linebacker group that played a key part in the NFL's top rush defense over that span, allowing only 82.5 rushing yards per game and 3.72 yards per carry. In 2020, Caldwell coached David and White to a Super Bowl LV title, finishing the season with an 11-5 record and leading the league in rush defense (80.6 rush yards allowed per game) for the second consecutive season. David averaged 112.3 tackles per season with Caldwell as his position coach and contributed 27 tackles for loss, 16 passes defensed, eight forced fumbles, 4.5 sacks, four fumble recoveries and two interceptions in that timeframe.
Before his first stint with the Buccaneers, he held defensive roles with the New York Jets (2015-18), Arizona Cardinals (2013-14) and Philadelphia Eagles (2008-2012). Caldwell began his coaching career as a training camp intern for the Philadelphia Eagles in 2007 before holding multiple roles on their staff from 2008-12.
An 11-year NFL veteran, Caldwell played with the Cleveland Browns (1993-95), Baltimore Ravens (1996), Arizona Cardinals (1997), Philadelphia Eagles (1998-2001), Chicago Bears (2002) and Carolina Panthers (2003).
He and his wife, Sue, have three children – two daughters, Sydnei and Saniah, and a son, Simeon. His daughters both played collegiate basketball at the University of Pennsylvania, while his son is a freshman safety at The Ohio State University.