It’s Christmas Day. Whilst all the other kids are opening presents and getting stuck in the box of chocolates before lunchtime, Regan Charles-Cook and his brothers were told to complete their daily run to ensure their fitness and endurance levels didn’t suffer during the festive period.
And that was the industry he chose, and it’s the industry he loves. Growing up in London and starting his journey within the Arsenal academy, Charles-Cook was about to embark on a career that would see him play and travel across the world.
“I was at Arsenal from the age of ten until I was 16,” the Grenadian international explained.
“It was a great base to start your football knowledge. I learnt my foundation there, and it was really good. There were some great players that are still playing now, and I also stay in touch with them. Ainsley Maitland-Niles was one; he’s in France currently.
“When I was told I would be leaving, it was weird. I grew up there, and I was there with my brother. I was going to leave, and they wanted to see me in one more tournament, but I’d been there for six years, so I wasn’t sure what else they wanted to see. So, I had a couple of offers from Norwich and Charlton, and that period was weird because if I chose Norwich, I’d be moving away from home, and I wasn’t keen on that.
“I went to Charlton. They’re known for producing some great talent, and I have to say, that is right up there with one of the best teams I’ve ever played with. The names are unbelievable. From back to front it was stacked with talent. Joe Gomez, Ezri Konsa, Joe Aribo, Anfernee Dijksteel, Ademola Lookman, Karlan Grant and Brandon Hanlan.
“And the strange thing was, in that team I used to play defensive midfield. I wasn’t always a winger. I was right-back at first and went to defensive midfielder. I actually made my debut at left-back. It’s no wonder you see me slide tackle.
“Charlton were switching managers constantly, so I went on loan to Solihull Moors, and that was where I started to play on the wing. Went to Woking for two spells and then Gillingham.”
Despite playing alongside some of these star-studded names, Charles-Cook insists one of the best things he ever did was move out on loan in the National League.
“It puts hairs on your chest,” he laughed.
“In my first game, a guy tackled me heavily and said, ‘This isn’t academy football anymore, mate.’ I was so shocked and taken aback. I got beaten off the ball, on the ball; I was just thinking, ‘This is real football.’ Academy football is nice, especially when you’re playing in a good team, but this football really brought out the physicalness in my game. There are so many good footballers in the National League; it was such a valuable experience. And it set me up for my move to Gillingham.
“I started really well there. They wanted me to move on, but I kept getting injured, and it was in my second year as we came into Covid that everything changed really, and I came to Scotland. The move was weird. I could stay at Gillingham, but I thought it was time to finally leave my comfort zone because if you look at all the clubs I’ve been at, they’re next to my house except for Solihull Moors, and even then, it was convenient there because my brother was at Coventry at the time.
“So, I needed to get the best out of me by moving away. It’s easy to go home to your parents all the time, whether you’ve had a good or bad game, and I was looking to challenge myself. The first year at Ross County was hard; I really did choose the worst time to move! Not seeing anyone, isolation because of Covid and being far away from home – it was difficult. My first year wasn’t a good year, and I was struggling.
“I 100% was homesick, but the second year, I started to get used to it more. I had a really good manager who took me in and put their arm around me. A lot of boys he signed I knew, so we all gelled together. Second year was great. But the beauty of it all was when you compare the first to the second year, it was beautiful. I have a lot of respect for Ross County; they’re a proper family club. From the kitman to the secretary Fiona, they’re so genuine.”
Having overcome the initial obstacle of moving away outside his comfort zone, Charles-Cook was catching the headlines. Achieving a top-six finish with Ross County, he was the league’s joint-top goalscorer for the season with 13 goals in the Premiership, which saw him nominated for the PFA Player of the Year award.
Interest in Charles-Cook was high, and now feeling more mature and capable of living away from home, he went further afield by signing for FC Eupen in Belgium.
“Europe is so special to play football,” he stated.
“It’s a whole different atmosphere and type of football. Going to play against teams like Brugge, Antwerp and Anderlecht was amazing. Standard Liège was my favourite. I walked out of the tunnel, and it was just smoke; I was so confused. The experience you get out there, you can’t buy. Learning a different style and playing against different players was a learning curve. There’s so much detail over there with lots of video analysis.
“Now you come into this Motherwell system; it’s the same level of detail, and that’s how you become successful. It’s working right now. I lived on my own over there, and people came out frequently. But the town I was living in was unique. Lights used to turn off at 6pm. Shops close at 6pm. It was crazy. There wasn’t much to do there, but there were cities nearby that I could go to, but living out there felt easier.
“Living alone is nice. When I go home now, I feel so overwhelmed. After three days I’m like, ‘I need my own space back!’ It’s always beautiful to see my loved ones, but the moves have built me up to be able to cook, clean and look after myself. I’m sure my mum has no worries about me now!
“On the pitch, it wasn’t always smooth over there. In my second season, we got relegated, which was horrible. We went down on the last day of the season, and it just hurt because every player wants to play at the top level. I guess it gives you the other side of that experience, but to be in different types of changing rooms, one where you’re winning and one where you’re struggling. But it also allowed me to become a leader because in the second division I was named captain.
“They saw me as a leader, and I had a lot of responsibility, especially because it was such a young group. The boys respected me, and I respected them. Leaving them was tough because I had led it for a year, but that’s football.”
Having decided that the time was right for his next move, the 2025 summer window would be a complicated one for Charles-Cook. Unsure whether he’d be playing abroad, in Europe, or back in the UK, he had some decisions to make.
“It was a weird window,” he laughed.
“I had some options, and then I spoke to the manager. I looked at the way Motherwell were playing and the things they were achieving, and I was blown away. I’ll be totally honest, the manager swung me to come here straight away. His philosophy was making sense to me; attacking football is attractive, and the composure he had the players playing with enlightened me. I like the ball to be on the floor; I can do the long ball thing, but you don’t become a footballer to play like that.
“He was firm and interesting. I sat down with my family, and I was saying to them how intriguing this all was. I watched some videos, and it was unreal. I couldn’t believe they weren’t winning every week. The first thing the manager has done here is bring in players with great personalities and people that are easy to bond with. Changing room dynamics are so important. You don’t want people who can ruin it.
“This is a family here, and we’re all around each other. Everyone wants everyone to do well because if the team is doing well, we’re all happy. When you see the depth we have, it’s incredible. I think we made 19 changes to the starting 11 over four matches or something. You have a full 25 to 30 squad that know their roles. You can take one chess piece out and slot another one in, and it doesn’t look any different. I’ve never seen that before.
“It’s a credit to him, the staff and the players. Everybody has taken the information in, and I’m so impressed. He’s done an incredible job.”
Whilst Charles-Cook’s club career is filled with interesting stories and is a unique journey, his international tales are also intriguing. The winger is eligible to play for England, Grenada and Jamaica. And with five brothers, the Charles-Cook family have made a bit of history together.
With three of his brothers playing football, in a Gold Cup qualifier back in 2023 against Guyana, he played alongside two of his brothers on the international stage.
“So my mum’s side, my grandad, is Grenadian,” he explained.
“My mum’s mum is Jamaican, and my dad’s parents are both Jamaican. It’s weird. My grandad came over and met my grandma. I could play for both; I did play Jamaica one time. The manager asked if I could switch allegiances, but I said I couldn’t do it now. Grenada is a big part of my career now. I played in the Gold Cup, and it filled me with so much confidence ahead of my second season at County.
“Grenada has my heart, and although we didn’t qualify for the World Cup this year, hopefully we qualify for the Gold Cup in 2027. That’s the task. But it’s made me so proud. My most incredible moment was playing alongside my brothers for Grenada. Us being on the same pitch at the same time was unreal, and I think it was a Gold Cup qualifier. You think back to those years in the back garden; one brother is a goalkeeper, one is a right-back, and the other one is left-wing. All those blood, sweat and tears from our parents making us do sit-ups and press-ups, ensuring we were training with each other, were all worth it for that moment.
“My older brother, Reice, got his call-up first, but he was trying to get me to go too. Then it was me, then it was my little brother, Roman. I didn’t go until I was 24, but that was because I was wanting to focus on my club career first, and then I went for the first time; it was one of the most beautiful things in my football career. I couldn’t believe I didn’t do it earlier.
“Representing the country was so special. It even brought a tear to my grandad’s eye. I’m trying to get some of the family to go to our next game. You don’t realise how many footballers are in different countries. Representing Grenada at the Gold Cup was the most competitive tournament I’ve ever played in. Football talent is all over the world. So, the goal is to qualify for the next Gold Cup. They’ve never got out of the group-stage before, so that’s a target.
“They’re getting stronger every year now as a squad.”
