Exeter City captain Pierce Sweeney has only played under three managers in his ten years at the club, so Caldwell's departure naturally feels unique for City's longest serving player.
As the longest serving current player for the Grecians and in his centenary year, Pierce has taken it upon himself to help guide his younger teammates through the wake of Caldwell's departure.
"We've got a really mixed group of ages in the changing room, with some players on their first loans, some older lads and some younger players coming through the academy."
"There's been quite a lot of speculation early last week, and there's been conversations between players. The manager has gone home to his family, so when I heard it was happening I understood straight away."
With Dan Green & Kevin Nicholson steering the Exeter City ship on Tuesday night, the Grecians reacted lately to grab a point against Wycombe Wanderers in a 1-1 draw.
"I thought in the first half we were quite loose in possession with too many unforced errors and too many uncharacteristic errors; we looked a bit unsure of what we wanted to do."
"In the second half it was very different, we were sure of what we wanted to do and how to go about things. We played forward and put the ball in the box, and I think 15 minutes before we scored the goal there was only one team that looked like scoring."
City now travel to the Weston Homes Stadium on Saturday where they will be hosted by Peterborough United.
"They score goals, there's no doubt about, they've got some talent at the top end of the pitch."
"But they also concede chances. They've conceded an awful lot of goals and an awful lot of shots on goal, so it's got to be something we're licking our lips about."
Hear more from Pierce below on Grecian+