Leo Castledine: Ex-Chelsea academy star on exit, Middlesbrough move and Premier League dream

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If you could plot out the perfect loan move as a young player looking to make a name for yourself, then Leo Castledine is the blueprint to follow.

The attacking midfielder, 21, was signed to spearhead Huddersfield Town's push for promotion from League One at the start of August. Five-and-a-half months, 29 games and 12 goals later, Castledine has established himself as one of the EFL's most exciting young players and earned a seven-figure move to the Championship with Middlesbrough.

Not bad going for a player who was earmarked for big things years ago in the Chelsea academy. Football has always been in his blood: Castledine's father, Stewart, played in the Premier League for Wimbledon in the 1990s.

Castledine Jr's start to the 2025-26 campaign has been so fruitful that he's already bettered the 11 goals Stewart accumulated throughout his entire career. "I was [aware] actually, which makes me happy," Castledine grins.

"He still has the one-up on me of playing in the Premier League but hopefully I can get to that soon!"

It could come sooner than expected after Boro, second in the Championship standings and chasing down Coventry City, were victorious in the battle for his signature last week.

A January move felt inevitable with Castledine catching fire in front of goal for Huddersfield and becoming hot property. His final act as a Terrier was to land the EFL Young Player of the Month award; the accolade for December follows a sensational run of form which saw the youngster plunder five goals and an assist.

His overall tally of 12 goals in half a season makes him a tough act to follow for a Huddersfield side who, by their own admission, were desperate to sign him permanently.

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Stewart now provides counsel to his son and Castledine, schooled in the AFC Wimbledon academy before being signed up by Chelsea, has never been intimated at the prospect of following in his father's footsteps.

"I think it's healthy pressure, which I liked having on myself," he says. "We've been competitive with each other since I was about five and so I think in a way that's almost made me strive for more. I want to play in the Premier League because of him.

"Going into the same field, you often hear a lot about players who have problems with parents being too hard on them or not really understanding [things]. I've never experienced that. He's never been too hard on me ever because he knows what it's like - the pressure that you're under from such a young age - so he's never wanted to add anything onto it.

"I know that I can trust what he says, so it's good."

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Castledine Sr is not the only face you'd recognise on a family outing. His mother, Lucy Alexander, is a well-known television presenter who hosted Homes Under the Hammer for over a decade. His older sister, Kitty, is a talented actress currently enjoying a breakout role in Eastenders .

In an alternate universe, she may have had company on the iconic BBC soap. Castledine also enjoyed drama and the arts in his teenage years and his participation in the media coincided with a crossroads in his football career just after starting secondary school.

A late developer physicality wise, Castledine was warned he could be let go if things didn't turn at Wimbledon.

"I'd been sat down and told, 'Look, by December you need to basically start playing better or you might not get a new contract'. And then I hit a really big growth spurt [the following year] and I gained quite a lot of size. I was playing in defence then and just sort of started getting a lot bigger and a lot better.

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"Then I started playing up a few age groups, which made me better technically. So then when I came down and played with my own age groups I'd feel like I was ready to start playing in midfield a bit more often, sometimes attack. It all started from there; I started to get a sniff of the goals and said there's no chance I'm not going back to defence!"

Like most Chelsea fans of a similar age, Castledine idolised Frank Lampard growing up. Fast forward to the current day and he and his new team-mates are out to chase down the Blues' all-time leading goalscorer in their bid to earn promotion to the Premier League.

Castledine's showreel has an air of the Lampards about it. As he grew older and progressed through the ranks at Cobham, Castledine became a student of Mason Mount . "We play similar positions and I'd watch him and try and take some of the bits of his game into mine," he explains.

"I was lucky enough to train and play with him and stuff. He was great with me, as you'd expect, having come through the academy. He made an effort every time we'd be out in training or in the building and stuff to kind of take me under his wing."

The affiliation forged with Chelsea in his youth made it harder to for Castledine to say goodbye for good earlier this month. The sobering reality for homegrown players at Chelsea, though, is that the pathway is far different now than it was for the likes of Lampard and Mount in years gone by.

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Castledine's dazzling form in League One meant that he had no shortage of suitors ready to make him a Championship player. The youngster was meticulous in deciding his next move and deemed Middlesbrough's style of play a good fit for his own qualities.

"I've always been a Chelsea boy but there comes to a time where you have to back yourself and look at how you want your career to go," he explains.

"Coming off a good half season at Huddersfield , I just felt the pathway at Chelsea [wasn't there for me]. Or if it was, it would just be including more loans, which I didn't feel was going to benefit me. And then a huge club like Boro come in and put a deal on the table - those things are hard to say no to.

"Boro are one of the best ball-playing teams in the league, which was one of the things that interested me so much about the club when they came in for me. It felt like [something] I was well suited to."

Ironically, Castledine made his senior debut for Chelsea against Middlesbrough back in 2024 during a League Cup semi-final tie. Their fates will continue to be intertwined and Castledine doesn't hesitate when he's asked what's next: promotion and the chance to emulate his father.

"That's what we're going for. Hopefully we can get there. I've committed my future to the club and yeah, I think it's every boy's dream to play in the Premier League. That's what we want."

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