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Gary was brought in on loan from Newcastle United, and was an instant hit, his performances propelling him into International recognition. These impressive matches were always going to attract the attention of other clubs however, and new Highfield Road boss Gary McAllister fancied him in his new side.
It's thought McAllister wanted to buy the youngster outright, but he had to settle for the loan deal as Gary signed new contract with Newcastle. Caldwell was out of contract this summer, but the fact that he is under 24 and a Scotland cap meant Hibs could not afford to pay Newcastle any compensation, ruling us out.
The news that Gary wanted to stay with Newcastle however, and Bobby Robson's willingness to let him go on a long term loan to get experience looked to be the perfect solution for us, but he chose the Midlands instead of Scotland.
Good luck Gary.