Chelsea’s 17-year-old midfielder who learned from his Wimbledon dad


“Things just don’t faze him.”

Chelsea’s Under-21s coach Mark Robinson has just been asked by The Athletic about Leo Castledine — another of the club’s fine young prospects — and he can barely contain the look of satisfaction on his face.

Robinson picked Castledine to start his first game in the EFL Trophy — a competition played between English teams from League One and League Two, plus 16 academy sides from Premier League clubs — against Peterborough United on Tuesday night. Aged just 17 and 94 days, he was comfortably the youngest player on the pitch.

This was no rookie Peterborough squad. The club are fourth in League One, and out of the 18 selected, 15 were also chosen for the 1-0 loss at Bristol Rovers last weekend.

As Chelsea cruised to an impressive 4-2 victory, you wouldn’t have known that Castledine had significantly less experience than the players opposite him. But then he is accustomed to playing against older footballers. It’s something he has been doing for some time and Robinson is aware of this more than anybody.

Robinson only took over as Chelsea Under-21s coach in the summer, but before that had worked 18 years at AFC Wimbledon, for the majority of which he had various roles in their academy (in the last 14 months of his tenure he was in charge of the first team).

Leo Castledine

Castledine playing for Chelsea Under-21s against Tottenham Under-21s earlier this month (Photo: Tom Dulat via Getty Images)

Castledine joined AFC Wimbledon at the age of seven having spent two years at Chelsea. Due to his small size they weren’t sure about taking him on at that stage, so AFC Wimbledon asked him to train with them instead.

He developed quickly, so much so that Robinson took him on a pre-season tour to Italy involving AFC Wimbledon’s under-18s when he was just 14 years old. What did he see in the teenager that made him think he could handle such a promotion?

“It’s just his character really,” Robinson replies. “It’s just the way he is. You knew he could handle it. Physically he is strong. He was standing out in his own age group so we just took him to give him a taste of the under-18 level early. As well as being a very good footballer, he has a tremendous attitude and he works very hard on his game too.

“I think because he has always done it since then, that helps him. He has always played at least one age group up if not more. He is reaping the benefits now.”

More from Robinson later. Obviously Robinson is not the only person to help steer Castledine’s development. For starters, there is his dad: Stewart Castledine, who was at Wimbledon between 1991-2000, during which time they were in the top flight. While not a regular, he scored seven times in England’s top division and went on to play for Wycombe Wanderers too. That’s a lot of experience to lean upon.

Castledine senior stressed the importance of a good work ethic, fitness, strength and a ‘never give up’ mentality, which was synonymous with the Wimbledon team he played in. For years the duo would play against each other, especially in the summer, keeping Leo’s fitness up during post-season. When he was younger, Stewart would inevitably get the better of Leo. That is not the case now.

Stewart Castledine

Stewart Castledine putting in a tackle while playing for Wimbledon in 1994 (Photo: Paul Marriott/EMPICS via Getty Images)

A number of leading clubs looked to sign Castledine from AFC Wimbledon after he was called up to play for England Under-15s. Getting selected at national level despite playing for a less fashionable club was always going to attract attention. He was offered the chance to move back to Chelsea and took it.

His family are Chelsea fans and live just 15 minutes from the training ground in Cobham, but another factor helped persuade him. Frank Lampard, who was managing Chelsea’s first team at the time, said he’d seen Leo in action and liked what he saw. It was a small but telling contribution to the process.

Lampard is not the only Chelsea stalwart among Castledine’s admirers. One of his first youth coaches was a certain Ashley Cole. Before he left to join Lampard’s backroom staff at Everton earlier this year he gave Leo one of his old England shirts, signed it and wrote encouraging words on the back.

Then there is John Terry. The former Chelsea captain has a part-time consultancy role with the academy. He regularly remarks what a great trainer Castledine is, how he treats each session like a cup final. That’s how Terry was himself when coming through the ranks — no wonder he spotted and liked it.

Like many Chelsea youngsters, Leo went to Whitgift School. Such was his ability at a number of sports, he was given a sports scholarship. Before he rejoined Chelsea in 2020 he was enrolled in the elite academy at Harlequins, a professional rugby club who play in the top division in England. They continued to send emails for a while asking whether he’d reconsider. Playing such a tough, physical sport benefited his football development.

Last season Castledine made 36 appearances for Chelsea. The majority were for the under-18s, although there was a debut in the UEFA Youth League, which is played at under-19 level. A sign of his rapid progress is that he has played 22 times in four different competitions this season, including the more demanding Premier League 2 and EFL Trophy (both for the under-21s). He has also captained England Under-18s.

Among the things still to be determined is what his best position is. Against Peterborough, he was one of two No 10s supporting striker Malik Mothersille. What does Robinson see Castledine’s best role as?

“We believe it is in midfield as a No 8, but he is also very versatile as well. He has played right-sided centre-back for the under-21s, he’s played wide for the under-18s. But wherever you put him, he gives absolutely everything.

“Not having one set position could be seen as difficult but it’s also good for him. Obviously as you get older you’re going to want to nail down a position you want to excel in, but it’s also good to have that utility thing about you where if you’re needed you can go in and play. Every player wants to play but if you have that versatility it is only going to help you do that.

“In terms of energy, he is similar to Mason Mount and Conor Gallagher. I think he has more elements of Conor out of the two of them. He can be very dangerous when he arrives in the box, is really good in the air, and we have to make sure we keep working on that as well. He is definitely going to be a goal-scoring midfielder.”

Leo Castledine

Castledine, in the front on the right, with his Chelsea Under-21s team-mates in October (Photo: Clive Howes/Chelsea FC via Getty Images)

During the 87 minutes he was on the pitch against Peterborough, he was neat and tidy in possession, playing in a number of different areas while linking up with his team-mates. One great example was when he built a Chelsea attack just after the half-hour mark, getting involved twice in the move before finding right wing-back Dion Rankine with a delightful 30-yard pass.

Conversely, there was a sloppy pass towards his own goal just before half-time which bypassed midfielder Cesare Casadei and found Peterborough striker Jonson Clarke-Harris instead. Fortunately, Chelsea defender Alfie Gilchrist came to the rescue. That was a reminder, Robinson explains, that there are still things to work on.

“Leo just has to tidy up here and there on a few things,” he says. “It’s sometimes about decision-making, when to play one or two touches and recognise the situation.

“But it’s also about not taking away that thing which makes him great, that dynamic running and surging forward. I’m really mindful of that with all our players — you can overcoach them and end up taking away things that people love about them.”

So what’s the plan going forward? He has already been invited on more than one occasion to train with the first team. Indeed, he played alongside N’Golo Kante and Ruben Loftus-Cheek in a pre-season friendly at Borehamwood in July, scoring Chelsea’s first goal in a 4-2 victory.

Graham Potter has taken a look at him too, and there is a possibility he will be asked to join a training camp in Abu Dhabi next month involving senior players not at the World Cup.

Chelsea will have a decision to make about how many under-21s players they want to go on that particular trip because it looks like it will clash with the next round of the EFL trophy, which is due to be held on December 14.

Castledine is also being watched by a number of clubs, but Chelsea secured his long-term future by giving the teenager a three-year contract in the summer.

He is clearly ahead of schedule and a loan in the future will be considered. But the dream of following in his father’s footsteps and playing at the highest level certainly looks a real possibility.

(Top photo: Darren Walsh/Chelsea FC via Getty Images)


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