The Scottish defender has played at such clubs as Newcastle United, Leeds United, Sunderland, Burnley, Wigan Athletic and Birmingham City and during his time in Britain, came across some very iconic people.
Steve allowed me to delve into his career and dig up some past memories which have helped shape the person and player he is today.
At Newcastle, Steve played under the late, great Sir Bobby Robson.
"Bobby was a real character. To learn at such a young age with a manager like that was a real honour. He was a phenomenal talker and motivator. He always seemed to know the right things to say to the team before the game to have them prepared properly. I still think about him on a regular basis."
"My first club was Blackpool. It was a real eye opener! Completely different from what I was used to. It'll always be a special club to me because it was the first time I played regular first team football.
"Bradford was a difficult situation. I signed for a Scottish manager called Jim Jeffries. Two weeks later he had resigned! I stayed a few months but it wasn't the same after the man who had taken me there had gone.
"Leeds is another club I feel a strong affiliation with. Just a fantastic football club. I was so disappointed we went down (in 2004). It still baffles me to this day with the players we had. I guess we just left ourselves too much to do to survive."
Caldwell then made the risky move from Newcastle to Tyne-Wear rivals Sunderland but he revealed that his shift across to enemy territory went without a hitch ..to some extent.
"Well, first of all I had a great relationship with the Geordie fans. I think they understood that I had given everything and that I wanted to play regular football at 23/24 years of age. I felt I had to leave for that to happen. Sunderland was the ideal choice for me. I met (then manager) Mick McCarthy and loved what he had to say about how we should go forward. Also it meant I didn't have to move! My time there had such great highs and awful lows. I felt that as I had played for Newcastle it restricted me from ever being totally accepted by the Sunderland supporters."
Then Manchester United legend Roy Keane took over at the Stadium of Light
"Roy Keane was one of the major disappointments for me in my career. I idolized him as a player. Sometimes as a manager I thought he had some great ideas and focus and then I felt he would become sidetracked and petty about things that weren't as important. Ultimately our relationship broke down and I moved on."
A move to Burnley followed and that is where Steve finally felt settled.
"Burnley provided probably my fondest memories in football so far. When I got there I sensed we were going places but we were a long way from achieving that! You could sense that we were amassing a squad that would eventually challenge. Once Owen Coyle arrived we had all the ingredients. Just an amazing bunch of characters, many guys peaking at the perfect time. If Owen had stayed we would not have been relegated (in 2010). I'm certain of that. Brian Laws came in and I had an injury-plagued season. He obviously felt I wasn't the right Captain that he wanted and I was on the move again."
An opportunity then arose at Wigan which brought Steve and his brother Gary together under Roberto Martinez.
"I first went to Wigan to keep fit. I didn't have a club and I was getting anxious. They allowed me to train and eventually offered me a year's deal. I'm very grateful to Roberto Martinez for allowing me to play there and learn under his tutelage. It was such an experience, probably the most I've learnt in my career, even though I didn't get the chance to play as much as I would have liked. Although I did get to play with my brother in the Premier League. I will always be extremely grateful to Roberto and Wigan for that opportunity."
Steve then found himself at Birmingham, playing in the Europa League, despite the Second City club dropping to the Championship.
"My first season at Birmingham was one of the most enjoyable seasons of my career. The Europa League was amazing. I was fortunate enough to have played in Europe before but to be there with a club who hadn't experienced it for many, many years was exhilarating. The experiences will never be forgotten. Our league form gathered momentum too. We played 63 games that season and unfortunately we ran out of steam in the end, losing to Blackpool in the playoff semi-final. I felt with 10 or 15 less games the next season we were in such a good position to achieve automatic promotion. Unfortunately though, Chris Hughton left for Norwich. We were not the same team without his guidance and we lost a few influential players to injury. We finished mid-table but it was a bitterly disappointing season for me and all concerned."
It then occurred to Steve to focus his attentions abroad and he ended up signing with Toronto in May this year. He has thoroughly enjoyed his time in Canada thus far.
"I received a call from my agent asking what I thought of joining Toronto on loan for an initial two-month period. I knew I was leaving Birmingham and I felt it was too good an opportunity not to experience. I was concerned I needed a break as I had played a lot of games but after talking with (TFC head coach) Ryan (Nelsen), he convinced me to come almost immediately. I'm glad I listened to his advice! It meant that I wasn't committing fully and we could both have a look at each other to see if the situation was right. I'm glad that it worked out and I'm extremely excited about the coming years. I feel that we are going to achieve great things."
It has been a pleasure to play alongside Steve at Toronto FC and I will be wishing the great man all the best for the future when I have to head back to Wellington after my loan expires soon.