Leo Castledine first interview after he swapped Chelsea for Middlesbrough after impressing on loan at Huddersfield
14:51, 14 Jan 2026
Leo Castledine signs for Middlesbrough
Leo Castledine signs for Middlesbrough(Image: Middlesbrough FC)
Leo Castledine pinpointed Middlesbrough’s recent history of promoting young players, and Kim Hellberg’s philosophy as the two key reasons behind his decision to join this month.
The young versatile forward signed a long-term deal at Boro after a deal was agreed with Chelsea. It followed a hugely successful loan spell at Huddersfield Town in the first half of the season.
That alerted a number of Championship clubs when it became apparent that Chelsea would look to recall and cash-in during the January transfer window, and it was Boro that ultimately won that race.
Asked why he chose Boro, the new recruit told the club website: "The manager’s philosophy and the way the club treats young players. You see so many young players coming through here and getting a genuine opportunity.
“That was the biggest selling point for me. I’ve come to a point in my career where I felt I needed to take that step into being a man and being my own player. I think joining a club like this will only benefit me.
“You can see the history at the club for playing young players and giving them a chance and trusting them if they can perform. I think I’m ready for that. That was a big factor for me coming here.
“Of course, the club are doing so well too. They’re winning games, they look a threat, which is everything I want to be. So I'm over the moon.
“It's a massive club and a big step for me. I think everyone knows that. As soon as I heard of the interest, it was a no-brainer for me. I wanted to get it done as quickly as possible and get up here."
Not signed in time to debut last weekend at Fulham in the FA Cup, Castledine has instead had an extended period to train for his new club and get to know his new team-mates at Rockliffe this week.
It’s expected that the 20-year-old will debut on Friday evening instead, when Boro make the trip to West Brom. On what fans can expect to see of the Chelsea academy graduate, he said: "I’m probably not your conventional ten.
“I like the gritty side of the game. I’ve played in defense before, so I’ve got that aggression. I like to press, I like to tackle, but I also love getting in the box and scoring goals - the things every attacking player wants to do.”
He joins the club in fine form too. He netted 12 goals across all competitions in the first half of the season, while on loan in League One with Huddersfield. Though he’s now stepping up a level, he’s certainly not short of confidence.
“It’s been a good start,” he said. “No one expects to fly straight away, but I managed to do well at Huddersfield in the first half of the season. And now I feel I’m reaping the rewards.
"I think it’s just playing with no fear. I’m never going to not do what I think is right in the moment. So If I want to take a shot then that’s what I’ll do. And if they keep going in I’ll keep taking the shots. I’ve got 10 goals so far this season and I’m looking to add plenty more to that tally here and hopefully help the club get promoted.”
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