Amongst his first words on returning as Wigan Athletic manager after leaving Exeter City were that we returns 'a better manager, a better person, far more experienced and ready for the challenge ahead.'
Caldwell has strong ties with the Latics, having captained the Latics' side that upset the odds to win the FA Cup against Manchester City in 2013 and then went on to lead them to the League One title in his first season as a manager in the 2015-16 campaign - his first full season in management.
However, Caldwell was dismissed five months after leading Wigan back to the Championship and indifferent spells in charge of Chesterfield and Partick Thistle followed before he was appointed as Exeter City manager as successor to the Rotherham United bound Matt Taylor in 2022.
At the time of his arrival the Grecians had just won promotion from League Two and were looking to re-establish themselves in the third tier with 14th, 13th and 16th placed finishes in the 2022-23, 2023-24 and 2024-25 seasons respectively.
In addition to this, he also guided City to the fourth round of the FA Cup in 2024-25, where they were beaten by Nottingham Forest on penalties, which was the first time that the Grecians had reached that stage of the competition since the 1980-81 season.
Whilst he never won a promotion with the Grecians, Caldwell will be remembered for being the guiding light in one of the club's longest ever spells in the third tier in modern times. All of this was achieved at the backdrop of the Grecians' Supporter's Trust owned model coming under threat. The club's run of 479 games with an academy graduate in the Grecians' starting line-up came to an end on his watch, as the challenge of unearthing another Ollie Watkins, Ethan Ampadu or Matt Grimes became increasingly harder.
Caldwell's immediate priority at the Brick Stadium will be to keep the Latics in League One, as they currently lie 22nd in the table - two points adrift from safety. With the Grecians currently on 39 points, his successor at St James Park also has some work to do to ensure that they will be playing League One football in the 2026-27 campaign.
