Having left Celtic for Wigan three years ago, Caldwell is ideally placed to analyse the pros and cons of moving from the Glasgow club to the English Premier League.
The financial rewards are greater down south, and games against the likes of Manchester United and Arsenal are obvious attractions. But right now, he believes, Hooper should stay and savour Celtic’s forthcoming Champions League tie against Juventus, knowing that any new employers in England may never get to the knockout stage of European football’s showcase tournament.
“If I was a player in Gary’s position then the Juventus games would be a huge pull to stay,” Caldwell said yesterday on a visit to his old school, Riverside Primary in Stirling, where he was unveiled as the first Tesco Bank Community Ambassador. “The opportunity to play twice against Juventus, and have a real opportunity to beat them and have four games in the Champions league knockout stages, is a huge pull.”
Hooper still has 18 months of his contract to run, and earlier this week he turned down an extension offer which his employers said was the last one they would make.
But, while resigned to losing Hooper eventually, Celtic manager Neil Lennon has said he is going nowhere for the time being – leading Caldwell to argue that the striker should count his blessings, make the most of his time in Glasgow, and remain confident that lucrative offers will still come his way later in the year.
“To have that chance of playing Juventus home and away and get to a stage of the quarter-finals of the European Cup that no Scottish club has ever reached in modern times would be a big pull for any footballer,” the Wigan player said. “It will be a difficult dilemma should the club accept a bid and Gary has a decision to make.
“In football, I would always believe you back yourself – you don’t jump at the first opportunity. If you back yourself there will be other opportunities in the future.
“I’ve never played against Gary Hooper, but have watched him this year, in the Champions League especially. He’s been very impressive. Not only his goals, but his workrate, his pace, the way he leads the line. He would be a great addition to any team down in England.
“Celtic is a great club, but they play in the SPL and you are not playing against Manchester United, Chelsea and Arsenal and Liverpool week in week out. Inevitably, players want to test themselves at a higher level. This window, Celtic are in a stronger position because of the Champions League and the Juventus games.
“I came to the Barcelona game at Celtic Park with some other players from Wigan and you’re sitting there and you’ve played on that pitch and you want to be out there.
“But with there being no Old Firm games this season, it’s really only the Champions League nights that you miss. The opportunity to play in that stadium with those supporters behind you is something you definitely miss too.
“But when the opportunity arises for you to move to England, that’s what you have to weigh up. ‘Do I stay for all this or do I go down south for a step up in my career and to push myself against the very best players in the world?’ That’s the decision I had to make and that’s the decision others will have to make too.
“The Premier League has the money, the biggest players, the biggest teams and, once a player has made his mind up, it’s very difficult to change it. But Celtic really understand that and they are doing really well and progressing in the Champions League.
“Is there any point throwing money at Gary Hooper if he wants away? I don’t think so, no. He’ll move on and they’ll get a lot of money for him and they’ll use it to get someone hungry to prove himself up here like Gary Hooper did.
“Clubs move on when they lose players. It’s three years this window since I left Celtic and the players and the whole club is completely different to when I left.
“Football moves on so quickly these days.”
With his Scotland debut now more than a decade away, Caldwell has seen several national managers come and go. Having worked with Gordon Strachan at Celtic, he welcomed his former boss’s appointment as Scotland manager and said that, as long as a player was giving everything to the cause, Strachan would give him his complete backing.
“I’m obviously really happy it’s him and I’m looking forward to working with him again,” added Caldwell.
“I had a great time at Celtic with him, learned a lot and improved as a player. Hopefully I can improve even more and learn more with the national team now. He’s very loyal to his players and sticks by the ones he believes in and sees they’re giving everything they’ve got.
“Right from day one of pre-seasons – which were pretty torturous – he finds out which players are going to stick with him and which players aren’t.
“From that, he sticks by the ones who are giving everything and he can get the best out of.
“He did that throughout my time at Celtic and I’m sure he’ll do that with the national team.”