No matter how many more caps he earns, and however many managers may yet come and go, he will be able to look each of them in the eye. Caldwell was unfailingly loyal to Craig Levein in public and in private but yesterday served as a reminder of how football brutally moves on. He sat at Scotland's squad hotel and spoke with the same respect and unswerving support for Gordon Strachan that he had for Levein, and just as genuinely.
Berti Vogts, Walter Smith, Alex McLeish and George Burley have also picked Caldwell over the course of his 11 years as an international player, a career which will deliver his 54th cap against Wales tonight. Caldwell was Levein's captain for the first two Hampden World Cup qualifiers against Serbia and Macedonia and he will lead the team out again for Strachan's first competitive match in charge.
Caldwell defended Levein to the hilt and, by the end, that meant he was in the minority. Yesterday, though, the Wigan Athletic defender maturely acknowledged the benefits of Strachan taking over. He could see that even if Levein always retained the loyalty of the players, he had essentially lost the rest of the country. "I think the mood has changed," Caldwell said. "And I think it helps that the new manager gets not only the backing of the players but the backing of the country as a whole. The fans, the media, everyone can see that he's the right man for the job. That helps the players. When we feel that backing from everyone, it can only be good for the team.
"The mood definitely needed to be lifted. When any manager loses their job things are pretty much at rock bottom. It's the end for him but the team are at rock bottom as well. We were all very disappointed because we liked Craig and tried our best for him. Sometimes things just don't work out in football. But we definitely needed a boost.
"We all liked the last manager, all had a good relationship with him, and were all bitterly disappointed it didn't work out. But as professionals we move on. The new manager brings new ideas, a new approach and that can freshen up the place, give the players a new impetus. Under the last manager, when it started going bad, it was very difficult to change that."
Scotland are currently bottom of Group A after four winless matches. Whatever alchemy Strachan may produce will surely be too late to salvage a qualification place. Having played under Strachan at Celtic, though, Caldwell's time on the training ground this week served as a refresher course in what he has always liked about him as a manager. "The strong points are his coaching and his willingness to improve players, to give information to players that will improve them as individuals and in their role within the team. This week we've spent a lot of time on the training ground getting his ideas across. We've watched videos and then taken that out on to the training ground. We will all know our job. The team will know exactly how we're going to approach the game."
Caldwell has fallen out of the first team at Wigan after suffering an injury against Liverpool. That will not prevent him starting tonight. "I don't know if I'm fresh, but I'm eager to play because it's been a few weeks since I played a game. I'm really hungry for it.
"I look at the three games [against Wales tonight, Serbia on Tuesday and Croatia in June] and we would have to win all three to have any chance of finishing second in the group. Friday night is the first of those. We've worked on a strategy to win the game so hopefully it goes right on the night and then take that confidence to Serbia. Forget where we are in the group, forget what's at stake. It's a game for your country. You want to win, every time."