Meet 18-year Chelsea Prodigy, Leo Castledine, And His Fascinating Family

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Adesina David

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May 14, 2023
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Here is the story of Leo Castledine who has a fascinating family background and interesting personalities to back it up.

Chelsea youngster, Castledine, hails from an amazing family, his father Stewart Castledine, aged 50, was a professional footballer for 11 years, and he played for Wimbledon and Wycombe Wanderers.

Castledine's mum is Lucy Alexander, aged 53, and she is a presenter who used to host Homes Under The Hammer, and his 21-year-old sister, Kitty who is an actress made her EastEnders debut on New Year's Day as Penny Branning.


Leo Alexander Francis Castledine was born in August 2005, in Kingston upon Thames, where he lived only 15 minutes away from the Cobham Training Centre.

The Englishman currently plays for Chelsea as an attacking midfielder and he started off in the Chelsea academy at age 5 before moving to one of the clubs his father played in - AFC Wimbledon when he turned 7.

Leo Castledine would go on to spend another 7 years there before moving back to Chelsea in 2020.

The English prodigy also boasts of some level of international experience growing through the ranks, all the way from the England Under-15 side to the Under-19 where he is currently.

He has appeared as an unused substitute in four matches already this season and is in contention to play a part in kicking off Chelsea's FA Cup campaign against Preston North End on Saturday, January 6, 2023.

Castledine once talked about his transition from defense to midfield in an interview with the BBC.

At the age of 14 in an interview with the BBC, the youngster said: "Moving from defence to midfield was a very gradual process for me. It took about two seasons.

"I was a tough-tackling center-back at the start of my U13 season and now, towards the end of U15 season, I am a center midfielder and sometimes play as a number 10."

Leo idolizes Mason Mount and Jack Grealish. He is currently worth 400k, according to Transfermarkt.

Leo Castledine signed a new contract with the Blues towards the end of 2023, a three-and-a-half-year deal, which will keep him at the club until 2023.

Following the contract renewal, Jim Fraser, Chelsea's head of youth development and recruitment spoke highly of the 18-year-old, saying:

“We are delighted Leo has committed his future to the club and look forward to seeing him continue his development here.

“He has been ever-present at Under-21 level this season, so we hope to see him keep progressing at Chelsea in the years ahead.”

Leo Castledine made his first appearances for the Chelsea Under-18s while still schooling in 2020/21, before captaining the side in several games and hitting double figures for goals the subsequent season.