Steven Caldwell #13 of Toronto FC jumps up to head during the game at Sporting Park on May 23, 2014 in Kansas City (Photo by Jamie Squire/Getty Images)
After spending the first three decades of his life in the United Kingdom, Steven Caldwell has found a new permanent home in Canada since moving to Toronto in the summer of 2013. Caldwell’s time in the Six has seen him wear the captain’s armband for Toronto FC from 2013 to 2015, serve as president of Canadian third-tier side Oakville Blue Devils FC from 2018 to 2024, and work as an assistant coach to John Herdman for the Canadian national team between 2019 and 2021. Today, Caldwell balances his time between raising his two sons, Will (17) and Robbie (16), and working as an in-game and studio analyst for Canadian sports channel TSN.
RG spoke to Steven Caldwell about his main influences, coaching Jonathan David at Canada, the biggest differences between English and American football, and more.
You had the chance to work under a legend like Sir Bobby Robson at Newcastle, what was that like?
“He was a great coach. He was every bit as charismatic and impressive as you can imagine from the outside. It was challenging because I wanted to play every week and at that time I was in and out of the team, but I’m very thankful for my experience with him and to be given a chance to play for Newcastle. I was very ambitious and wanted to play more football, so there were times when we would clash, but when I look back now, I see a lot of the lessons that Sir Bobby taught me that I still hold to this day. In the end, we understood what we were both trying to achieve and gained respect for each other. We finished on a great note when I returned from my loan spell at Leeds, played the last couple of games and completed my Newcastle journey quite nicely by helping them qualify for Europe. I only have great memories of Sir Bobby and I’m so grateful that I got to play under him and learn so much.”
When did you realize it was the time to leave Newcastle?
“When I was 22, I was striving to play regularly and realized it was going to be very difficult to do so in Newcastle. I saw all the players that Newcastle were signing… I was getting 10-15 games a season and I knew that I had to drop down a level. I tried to leave in the summer of 2003 and it never quite worked out. I went back and there was a little bit of tension, but ultimately, I just wanted to be a regular and thankfully. Mick McCarthy and Sunderland gave me that chance. When I got the chance to meet McCarthy, I realized that he was going to be a great influence on my career. He was going to be tough on me, teach me some things and help me improve as a player."
Are there any players you looked up to as a footballer?
“I admired guys like Nemanja Vidić and John Terry, guys who were known for their defending and weren’t exactly flamboyant passers. I was never as good as him, but Terry is someone who I watched and admired, I strived to be as good as him and tried to emulate him.”
You were part of the Newcastle side that played Champions League football for the second time in club history. What was it like to watch them return to Europe’s premier competition after two decades in 2023/24?
“I watch Newcastle a lot, my boys are Newcastle fans and we’re part of a little supporters club here in Toronto. I think they can go very far and win a trophy this year. The challenge is going to be to kick on to the next level and push for the league title, but they need to fix their revenue streams so they can have more potential to sign players. They have the money, as we know, but with Financial Fair Play, there are restrictions to what they can spend.
They need to be as ambitious as their best players like Alexander Isak, Bruno Guimarães, Sven Botman, and Anthony Gordon, and add pieces to support them, but I think Eddie Howe has done a wonderful job.
He seems like the right man for the job and completely understands what the fanbase wants in terms of the style of football, and if he brings them a trophy, he’ll be a legend at that club.”
What was it like pursuing a professional football career at the same time as your brother?
“There's always competition between brothers, but there was certainly a closeness between Gary and I and we still speak most days. We helped drive each other on through our careers. We started at the same club, Newcastle, and played together at Wigan during the end of our careers. To play with your brother for Scotland is one of the biggest achievements, if not the biggest. It’s really special…there’s not a lot that can compare to it. There was a healthy rivalry. Being the older brother, I gave Gary a lot of milestones to hit, and he surpassed them on a lot of occasions which I'm very proud of. I don't feel any jealousy about my brother and his career. I'm so proud of him and what he achieved, and I'm glad that I played a partner alongside them. We came from a family that was very proud and loving, but was always “Right, what's next? What can you do more of? How can you achieve greater?” You know, we never really dwelled on success. We always look to the next thing, and we probably still do so. That's just the way that we were brought up, and I think it helped form our personalities as footballers.”
You had the chance to play in England’s top three leagues, how would you differentiate between them?
“I thoroughly enjoyed my time at League One with Blackpool, that was my first professional experience. You were going up against guys who are fighting for contracts, fighting to provide for their families…it taught me what it meant to be a professional. Then I wanted more and went to the Championship. The difference between those and the top-flight is you can’t afford to make a mistake in the Premier League. You can’t afford to be out of position…there’s too much talent and you’ll get punished, somebody else will take your place, and it's hard to get back in.”
What were the main differences between English football and MLS?
“The level of football surprised me in MLS. There was a lot of quality, a lot of young players that I didn't know a lot about, but it is different. It's a summer league, so it’s slower than English football. The biggest difference is in training. In England, every single session matters, every small side of the game matters, and in MLS, sometimes the training is just a little lackluster, so the challenge for MLS is to keep the level of coaching high and make sure the standards are met every single day."
What does your normal day look like?
“A lot of variety. I’ve gotten the chance to have a lot of different projects on the go. I always try to challenge myself, exit my comfort zone, and try new things. If we’re preparing for a major tournament, I’ll be fully engrossed and working 24/7, researching and creating documents to allow me to be at my best.
Since I retired, I’ve been able to put a lot of emphasis on getting my kids to school and taking them to football practice.
They love football and are always coming with me to football matches or to the studio…I’m trying to set them up for success. My eldest son has an athletic scholarship to play for Georgetown University in Washington D.C. so I’m quite excited for that, he’s going to have an amazing experience there and learn a lot. I love spending time with them. I look forward to sending them away to university, but I’m a bit apprehensive as well because we have such a strong relationship. I’m very proud of them.”
You worked as John Herdman’s assistant coach for Canada. What was your impression of Jonathan David and how good of a striker is he?
“He's a tremendous player. He's a very smart player who understands what’s asked of him defensively, he’s second to none in attack. You don’t have to repeat things to him too often, he gets it quickly. He’s a humble, down-to-earth, hard-working guy. He quietly goes about his business and does his job, he scores a lot of goals, and I think he’s going to keep improving through his mid-thirties. His brain is so smart that I think he’s going to keep improving. It was a pleasure coaching him…he’s going to go somewhere huge this summer.”
Lille look set to lose David for free, how important is it that Bayern avoid that similar fate and keep hold of Alphonso Davies?
“He's a huge asset, and historically, Bayern don’t lose top players for free. He's played most of the season for Bayern and is one of the best left backs in the world. If he does leave, he’s going to have plenty of options. A lot of his game is based around his elite athleticism, so if he can keep up his unbelievable power and pace, he’s going to remain in the top of the game for a number of years.”
Where does Newcastle’s Alexander Isak rank amongst the best strikers in the game?
“He’s a top five striker in the world, there’s no part of his game that’s missing. He works hard, he's quick, can hold the ball up, scores goals and has a great presence in the box..alongside Erling Haaland, he’s the best striker in the world in the six-yard box. He's got great vision and looks like a great teammate, he’s taken some great strides this season and improved a lot. Newcastle need to put the pieces around him to keep them there.
He’s one of the best in the world and is going to want more and pick up trophies, so Newcastle will have to match his ambition in order to keep him.”
Ben Doak is enjoying a fine loan spell at Middlesbrough…at 19, how high is his ceiling?
“It's pretty high. It’s going to tough to break through at Liverpool, but he’s doing excellently at Middlesbrough and will certainly be fancied by a lot of Premier League teams is Liverpool decide to let him go. I think Liverpool have high hopes and will give him a chance in the first team after this loan spell. It’s been a great season, and he's establishing himself in the Scotland side. He's different, he's quick, he's exciting. He's a player that we don't necessarily have in the Scotland squad. He’s going to keep getting better and working hard… I’m super excited to see where his career takes him.”
Toronto FC have missed out on the playoffs in each of the last four years…what’s going wrong for them?
“It’s been a tough time for Toronto. I don’t know if they have a lot of space to change things around. The recruitment has been a bit off in recent years, but you can turn things around quite quickly in MLS. I don't have a ton of expectations for them in 2025, but maybe that will be a good thing and help take some pressure off. The organization has to make the right moves to put the right people in the right spots to help them achieve success.”
Lastly, what have you made of Jesse Marsch’s start to life as Canada manager?
“I knew Jesse from his spell with the Red Bulls, I’ve spent some quality time with him… He’s a great guy. He’s very passionate about football and wears his heart on his sleeve, he’s down the line and opinionated, he’s just a good football guy you can have a conversation with. I’m really happy Canada have him, he’s perfect for the role and has already shown he can get the players to buy into the role he wants to play.“
Zach Lowy is a freelance football journalist who has written for leading outlets like FotMob, BetUS, Apuestas Deportivas, and who has appeared as a radio and television guest for BBC, SiriusXMFC, and various other platforms. After pursuing a global sports journalism degree at George Washington University, Zach has been able to tap into his multilingual background and interview major footballing figures in Spanish and Portuguese as well as operate the weekly podcast 'Zach Lowy's European Football Show' on BET Central.
