The Chesterfield boss insists that his sides should get the ball down and pass it around, building from the back and attempting to dominate possession.
It was at St James’ Park that he began his footballing education as a 16-year-old alongside his older brother Steven.
He credits his Newcastle United coaches and former clubs like Derby, Hibernian and Celtic, for helping him to develop a taste for passing football.
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Even, somewhat ironically, his experience as an international defender for Scotland helped shape his fondness for keeping hold of the ball.
“I got brought up with Alan Irvine and Tommy Craig at Newcastle, who, as with most academies teach you to play football,” he said.
“But they were proper teachers and showed me how to play the game, not just passing out but different ways to play.
“I always seemed to end up at clubs who played football, whether it be Hibs, Celtic, Wigan, I never seemed to be in a team that played direct football, because I wasn’t that type of player.
“Having played in those teams and got success in those teams that way, and even playing with Scotland against teams when you had to chase the ball for 90 minutes, I recognised that it’s far better to have the ball than not to have the ball.
“If we’ve got the ball, the other team have to win it back and then score. We just have to score, that’s all we have to work out.
“I realised pretty young that this was the way to go.
“As soon as I got the Wigan job I knew exactly what I wanted to do.”
The ‘Caldwell way’ of playing has already brought success – he points to a League One title earned with Wigan Athletic – and he insists it will bring more.
But it’s not without its downsides, at least in the short term.
“It’s the hardest way to play,” he admits. “I think Graham (Barrow) said it at a question and answer event, it’s definitely the hardest way to play football.
“But for long-term success it’s the best way. We aren’t playing 50:50 football, we’re in control of our own destiny, we have the ball and we’re in control of the game.”
The reason, he says, Chesterfield have encountered some difficulties in the early part of the new season is not because they’ve struggled with the ball, or even particularly without it, but at that moment when they first turn over possession.
That helped contribute to a rather unhealthy goals against column after just two games of the 2017/18 campaign.
Both Grimsby Town and Sheffield Wednesday found it all too easy at times to attack right through the heart of the Town midfield, having won the ball.
It’s not a new problem for the 35-year-old and once mastered, he says it will be key to the Spireites’ success.
“What we have to improve on is transition, so when we lose the ball we have to defend better in transition,” he said.
“It’s not an issue when we’re in the defensive block, I think we’re fine.
“But when we’re in transition from our expansive shape when we have the ball, to not being in that, we have to improve.
“It’s a process I’ve been in before. At Wigan we lost two goals in our first four or five away games in the league. One was here, we won 3-2.
“I understand that in the beginning, you lose goals. It’s something that happens because of the way you’re playing.
“The team have to learn quickly that when we lose the ball, the game has to stop, or we win the ball back quick and high up the pitch.”
Caldwell has come in for criticism from the stands due to perceived weaknesses in the side and drawbacks in the way he sets them up.
He’s aware of the opinions of those who don’t see eye-to-eye with his style of play, but he is in no doubt that if the players get it right, he’ll be proved right and taste succes once again. “We’re in that process at the minute where everyone can question it, everyone can say the style of play is wrong, but the style of play is not wrong - the style of play is right. It takes time for it to bed into the players, for players to understand it. Once it comes, then it’s fantastic to watch first and foremost, but it wins games of football.Ultimately, it wins leagues and that’s what we’re trying to do.”