The start of my professional career was at 16 years of age, signing for Newcastle United of the English Premier League. There I made 37 appearances, many of which under the direction of legendary Manager Bobby Robson, before moving across the Tyne River to arch rivals Sunderland AFC. After an eventful two plus years that included the thrill and reward of Premier League promotion by virtue of winning the Coca-Cola Championship League title in 2004-05 and the disappointment of relegation in successive seasons, I signed for Burnley FC. The highlight of my time at Burnley FC was captaining a surprising and unlikely triumph against all the odds in the Championship League Play-Off Final at Wembley Stadium, earning Burnley FC promotion to the English Premier League after a 33yr absence from the top flight. Following the time at Burnley FC saw spells at Wigan and then Birmingham City where the club qualified for Europa League, their first European campaign in 50 years.
During my playing time in the UK, I was honored and proud to have been selected to play for the Scottish National Team, making 12 appearances over a period that spanned a decade. This experience of personal national pride was made especially rewarding by having opportunity to share in it with my brother, Gary Caldwell. To fulfill childhood dreams of playing alongside each other on the same pitch while wearing the badge of Scotland was an emotionally crowning moment.
The final stop in my journey as a professional player found me relocating our young family across the Atlantic to Canada to play for Toronto FC of Major League Soccer (MLS). After 2 seasons where I served as Team Captain and Player Union Representative, I made the difficult decision to retire to allow myself to concentrate on a business role within the organization in an effort to raise awareness of TFC in North America while helping grow the business exponentially. Most rewarding of all was also serving as TFC Club Ambassador that provided an opportunity to get personally involved in many worthwhile community efforts, many of which I continue to be involved with.