He was loaned out to Hibs by Sir Bobby Robson, played 11 games, and returned for a showdown with the Toon boss.
Robson said at the time: "He came knocking at my door in tears, begging me to let him sign for Hibs, saying he was homesick.
"In the end I was sick of the tears and let him go."
The Stirling-born Caldwell won a few tin-pot cups in the "Two-Club Chilly Jocko League", and went on to play for Scotland in their quest to qualify for the finals of a competition (failing, as always).
But the defender has never looked Premiership class, and I don't think he would ever have made the grade at St James' Park.
He certainly wouldn't get into the team today, with Steven Taylor, Fabricio Coloccini and Mike Williamson fighting for two places,
He started his career at Celtic, but they cast him out.
At 16 he came to England, alongside his elder brother Steven at Newcastle United.
Breaking through from the reserves proved difficult, however, and in search of first team football, he went on loan to other clubs on several occasions: Darlington and Hibernian in 2001–02, then Coventry and Derby County the following season.
During the 2003–04 season, Caldwell was given a free transfer by Newcastle. He signed a short-term contract with Hibs for the second half of the season, and during this period he played in their defeat by Livingston in the 2004 League Cup Final.
After going on trial with Vitesse Arnhem in the summer of 2004, he signed a two-year contract with Hibs. During the 2005–06 season, rumours circulated that he had signed a pre-contract agreement to join Celtic in the summer of 2006.This prompted Hibs fans to jeer Caldwell when he made a mistake in a game against Aberdeen. After this, the deal was confirmed by Gordon Strachan.
During the 2009–10 season, Caldwell had a contract dispute with Celtic, claiming that the club were "kidding themselves" if they thought he would accept their offer.
New manager Tony Mowbray, who had also worked with Caldwell at Hibernian, responded by stating that he would not ask the board to increase the offer.
Wigan AthleticCaldwell eventually signed for Wigan Athletic on a four-and-a-half year contract for an undisclosed fee on 13 January 2010.
Source: FOOTYMAD
