“It will be special to come back, even if it will feel a bit strange, being there in a different kit and team,” says Kyle Dempsey, who returns to Brunton Park with Bolton Wanderers this weekend.
“But the Carlisle fans know what I’m like. You know what I’m like. I never treat games as a friendly. Even though it’s a team close to my heart I’ll still be giving 110 per cent to try and win.”
Yes, we do know what Dempsey is like. We remember him well: the tough teenager who forced his way into Carlisle United’s team and played so well in his first full professional season that, by the end of it, he was off to the Championship.
That was seven years ago. Dempsey, via Huddersfield Town, Fleetwood Town and Gillingham, is now a Bolton player, and tomorrow’s pre-season game is his first opportunity to play at his old stadium since then.
It means a lot for the 26-year-old from Maryport to come back. As we relive Dempsey’s formative years at Carlisle and what he has done since, his affection for United comes across in passionate detail.
He came through the youth ranks from eight and became one of their most exciting home-grown players for some time: an attacking midfielder with ability, a powerful physique and a narrow-eyed determination.
In 2014/15, whilst still a teenager, Dempsey was United’s best player as they scrambled to League Two safety. His confidence on Brunton Park’s green turf glowed.
Dempsey says he will always appreciate the “platform” Carlisle provided. He was given his debut by Graham Kavanagh in 2013/14 before becoming a key player under Keith Curle the following campaign. He was also entrusted with the captain’s armband in his teenage years. “I still see that as a huge privilege and honour to be able to say that,” he says.
He talks about the Carlisle youth coaches who helped shape Dempsey at a time he was equally promising in rugby league. “David Wilkes was massive for me,” he says. “He took me under his wing, offered me a youth team contract at such a young age, and nurtured me and put me in the right direction.
“Another coach that stands out was Barrie Mossop, who also [organised] the ball boys. I had a really good season, when I was around under 12s-under 14s, and he was really good with me. He gave me a lot of confidence at such a young age.”
Dempsey, when he broke into the first team, certainly did not lack for confidence. He had the certainty about his game that many nervous teenagers lack. Where did that come from?
“I think a lot of it is down to my dad [Mike Dempsey, the former Workington Town rugby league player]. At a young age he had me on the field every day, made sure I didn’t miss a single training session.
“I was balancing football and rugby, and he was the one who said he felt like football would be my best option and seeing how far I could get.
“After every single game I still ring him now, to see what he thought I did well in, and he’ll always tell me what he thought I could have done better at too. He’s been the driving force of the standards I require.
“In myself, I’ve always had that confidence too. If you go onto the pitch and you’re not confident and don’t feel you can be the best player it’s going to have a negative impact on you.
“Even though I was 18 and had all these players around me who’d played 3-400 games, I believed in the ability I had and the mindset I had. I think over the course of the season I proved it in my performances.”
United’s 2014/15 was a traumatic one but Dempsey, in scoring 11 goals from 47 midfield appearances, was a shining light. “The senior players, when I had chats with them – like Gary Dicker, Danny Grainger, Stephen Elliott – all said I was being relied upon to be out there performing. I was the one who was creating and scoring the goals, alongside [Brad] Pottsy, who had a really good year as well.
“I wanted to be the best player on the pitch and I believed I actually was. At the end of the season I was rewarded with all the player-of-the-year awards, which was massive for me."
Dempsey says his personal highlights include scoring twice on his full home league debut against AFC Wimbledon, and “jumping about nine foot in the air to score that crazy header at Northampton”.
Another memory is telling. “There was the game against Accrington, where we got beat 3-1. In that game we looked lost. There were comments from the fans after the game saying I looked like the only one out there who actually wanted to deliver and get us over that line.
“In the second half I went out there and probably should have had three or four assists. I picked the ball up from 30 yards out, went past a couple and smashed one in with my left foot.
“After that game there were conversations [suggesting] we didn’t want to be here. I stood up and said I didn’t feel like that was the case. I felt I gave everything.” Dempsey was a strong voice as well as a leading player, and had started to attract transfer interest from the winter.
“From December, clubs were contacting [Carlisle] regarding me. This was all new to me. I was just a young kid playing first-team football for the first time in my life. I didn’t really understand what was going on.
“I had to get an agent who helped me through it. There was probably a patch where my performances did dip a bit. I was confused with talk of clubs in the Championship and League One wanting me. There were bids coming in getting rejected.
“I can openly speak about this now – I knew lads were on a lot more money than was in the contract I'd been offered [at Carlisle]. I didn’t think that was right, because I was the top scorer and top assister at the club. I thought, 'If I’m the main player here, week-in, week-out, I don’t deserve to be on less than anybody at this club'.
“Fans started getting a bit frustrated with me. I remember a few games when I’d be taking a corner or a throw-in, and a few saying, ‘Sign the contract, you’re not bigger than this club, you’re just a young kid’. They didn’t understand the situation I was in.
“I eventually got offered a contract that I felt was fair. I think that also showed my mentality as a young player. I wasn’t gonna accept mediocre. I believed how good I was.”
Dempsey signed the new deal but, in the summer, several clubs moved to trigger a buyout clause. Huddersfield proved the most tempting option and Dempsey departed.
“It was absolutely huge, moving from League Two after one season to the Championship. It was a ‘pinch me’ moment. Some of the players I’d be coming up against, the teams, the crowds…I was thinking ‘wow’. This is where I want to be.
“I was a bit naïve at Huddersfield, though, thinking I should have been playing a lot more. I was only 19 and had come from League Two. I had to find my feet. But that’s the character I am.
“I couldn’t get that run. I then had a really good pre-season and felt I had a chance of starting, but wasn’t even in the squad. That’s when I went to the manager and asked to go on loan."
So began Dempsey’s association with Fleetwood which, after a season-long loan in 2016/17, turned into a permanent spell. He played 146 games for the League One club over four campaigns, under Uwe Rosler, John Sheridan and Joey Barton.
“I thought it was great,” he says of his time there. “We had two play-off runs and I felt I delivered performances at a high standard. Probably one thing I lacked was the goals and assists to go with it. But I played numerous different roles there, becoming more a ball-playing midfielder rather than one who’s box-to -box.
“The way it ended wasn’t the best. I haven’t really spoken about it in detail and I probably won’t. There was just a disagreement over my contract after I picked up a little injury. But the fans were unbelievable with me and I enjoyed it.”
A move to Gillingham, in 2020, suited Dempsey. He was made captain by Steve Evans and given the status which suited his ambition. “I’ve always known I was a leader deep down, but I've probably not been the most vocal. I’d normally leave it to the captain and vice-captain. But I’ve always had something to say in the dressing room.
“For him [Evans] to have that belief in me, to make me the main man...it drove me on. I found my touch back in front of goal, started chipping in with assists again, and had an all-round really good year.”
Evans is a notorious character in the lower divisions, but Dempsey has only warm words for the Scot. “He’s a strong character, everybody knows that – seeing him on the sidelines, he obviously wears his heart on his sleeve.
“But he just drove us to be better every single day. I’ll always have very kind words and love towards Steve Evans. He gave me so much confidence on the field - a bit like Keith Curle did at Carlisle. Just allowed me to express myself and deliver the performances I knew I should be delivering.
"He always bigged me up in the press after I played well. He made me feel on top of the world.”
An impressive season-and-a-half in Kent put Dempsey back in the sights of admiring clubs, and on January deadline day this year he was set for Bolton. Having only made it home to Maryport three times during his Gillingham spell - Covid being a factor, as well as the distance - returning north appealed, as did the club itself.
“It was a bit of a crazy day,” he says of the move. “Gillingham were waiting to get a centre-mid in, and I was driving up with the thought I actually could be coming back.
“I didn’t really know what was gonna unfold, but my heart was set on Bolton. When I spoke to the manager [Ian Evatt], the coaching staff and Sharon [Brittan, the club’s chairman], there was so much positivity and drive of where the club wanted to go in the next couple of years.
“The way they played football suited me down to the ground, and it seemed such a lovely family club as well. I just felt at home straight away. I felt like I gave everything for Gillingham and I hope they felt the same when I left.”
Dempsey says that, because he returned too quickly from a knee operation in his latter Gillingham weeks, he was not operating at 100 per cent in his first half-season for Bolton. He picked up niggly injuries, but believes he is in the right place now.
“I’ve come back for pre-season like a totally different player. I feel strong again. Sharp. I’m able to do everything I want to do on a pitch, whereas last season I wanted to make certain runs and do other things but wasn’t able to do it.
“Now I feel I’m at a strong stage. I knew exactly how the gaffer wants me to play, I’ve had numerous meetings with the coaches, the details of positions where I need to receive the ball, my different role in this team…I’m loving every minute of it and really excited to see how the season unfolds.
“I still feel like I can play in the Championship, and now I feel I’m at a club where the aspirations and drive is to get to the Championship, and we’re not going to settle for any less than that. We just need to deliver on a consistent basis.”
Dempsey is not the only Cumbrian on the Trotters’ books. In goal they have the highly promising James Trafford, the 19-year-old Manchester City loan keeper who comes from Greysouthen. He was on Carlisle’s academy books until the age of 11, and recently earned his first England Under-21 cap.
“He’s a great keeper,” says Dempsey. “He’s a big character as well at such young age, and I think you need that. You can see the confidence he possesses and you can see how highly City rate him with the contract he’s just signed to 2027.
“It’s nice having someone who understands back home and how it is. He’s based near Cockermouth, and it makes the drive easier, because we can spell each other off. He drives one week, me the other week. He’s a great lad and has got a really bright future.”
It must also be reassuring to have another Cumbrian accent around the place. “It is,” Dempsey laughs. “His is a bit stronger 'cos he’s still a young age. I feel like I’ve lost mine a little bit…but six weeks home and it's back. I’ll never totally lose it…”
Dempsey - whose team-mates also include ex-Blues Jack Iredale and Gethin Jones - has not lost the connections with his boyhood club, either. “I still speak to Danny Grainger; he always tracks how I’m doing," he says of old Carlisle team-mates. "I still speak to Pottsy, [Mark] Beck, [Mark] Gillespie, who I was in the youth team with. Patrick Brough – his family and my family are really close and always together.
“I still keep in touch with Eric Kinder as well – I always will. He was the one who brought me through as a 15-16-year-old and put me in the youth team. He gave me that experience, so when I did come into the first team it didn’t feel much different.
“I still speak to Graham Kavanagh a lot. He gave me my debut and so many games at a young age. When Keith Curle was in the play-offs with Carlisle [in 2016], I dropped him a message saying all the best; we were in the play-offs with Fleetwood and he sent the same back. I will never have a bad word to say about Keith Curle. He believed in me from day one.”
The other people who constantly believed in Dempsey will be at Brunton Park this weekend. “My family come to every single one of my games. My mum, dad, my grandparents all get down to watch. That’s really special for me, especially my nana and granda – for me to see their faces at the end of games and how proud they are, it means the world to me.
“And my mam and dad, for the amount of miles they put in, taking me to Carlisle, down the country on a weekend to play games…they have been absolutely everywhere. No matter where I go, they’re by my side. To repay them with the career I’ve had so far, and make them as proud as they are, is really special.”
It will also, he underlines, be special to be back on home soil tomorrow. Dempsey hopes this won’t be the last time he plays at Brunton Park.
“I’ve always said it…I would love to finish my career there,” he says. “With how I feel physically, and how my body is, I feel I can play to an older age. I would 100 per cent want to finish my career where I started, maybe a season or two seasons. I think it would be fitting.”
It is hard to imagine Dempsey, the former teenage tyro, as the father figure in a younger Carlisle side. But he very much likes the idea. “Maybe when my legs have gone and I can just sit in front of the back four and spray balls around,” he smiles. “That would be perfect.”
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