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He admitted he'd heard nothing on a new contract so was not surprised when Brian Laws released him and confirmed it was probably time for a change.
He was very quickly linked with a move to Wigan where he would team up with brother Gary but that all went quiet as did a potential move to our Championship rivals Preston.
When Steve Cotterill was appointed as new Portsmouth manager last week I wondered whether he might try and sign some of his former Burnley players and the name of Caldwell was the first that came into my head.
This morning it is being reported that he could very well be Cotterill's first Portsmouth signing.