Dutch youngster to make U-turn on his decision to leave

In surprising news that has very much come out of nowhere this morning, it is being reported by various sources that Juan Castillo is now expected to stay at Chelsea.

The highly-rated Dutch left-back, who is also very comfortable in playing on the left-hand side of midfield (be it at left-midfield or as a left-winger even), was expected to leave the club once his contract ended this week (June 30th).

Speaking back in April, the 19-year-old admitted to Dutch media that he did not expect to break into the Chelsea first-team and would have to seek opportunities elsewhere.

“Because of what I’ve seen and gained over the past few years, I don’t think I’ll break through at Chelsea. If you come in as a youth player, you’ll always stay that way.”

Having made 96 appearances (scoring ten goals and creating twenty-two assists) at youth level for Chelsea since joining from the famed Ajax academy in 2016 (along with 11 appearances at international level for various Netherlands teams), it appeared that his time at the famous Cobham academy was coming to an end.

But what appears to be a positive turn of events, Castillo looks to have made a U-turn on his decision to leave Chelsea and will now stay at the club, with him even apparently signing a brand new contract as early as today.

Former academy coach Jody Morris – who is expected to return to Chelsea this week to be Frank Lampard’s assistant for the first-team – holds Castillo in high regard, making him a fundamental part of his 3-4-3 team (playing at left wing-back) that won the 2017-18 U18 Premier League and consecutive FA Youth Cups in 2017 & 2018.

Maybe the return of Morris and Lampard being a key factor in his decision to now stay? We shall see…


Before today’s (expected) announcement, Chelsea was going to go into the 2019-20 season with a scenario of four players that could play in the left-back position.

Emerson, Marcos Alonso, Jay Dasilva and Ola Aina.

Emerson is expected to (and has been since the turn of the year, to be honest) the main left-back for the first-team going forward.

Marcos Alonso is – at this moment in time – now considered to be the back-up to Emerson, although that appears to change with the Spaniard expressing his desire to leave the club (with La Liga side Atlético Madrid wanting to bring him back to Spain) after being dropped by Maurizio Sarri for the UEFA Europa League Final against Arsenal.

Jay Dasilva is returning from a positive season on loan at EFL Championship side Bristol City, narrowly missing out on the play-offs, before representing England at the UEFA European Under-21 Championship. (UPDATE – Jay Dasilva officially re-joined Bristol City on a permanent basis for an undisclosed fee on a four-year deal)

Ola Aina is another one to have had a positive season away from SW6, being one of the surprise players in Serie A last season with Torino, with the Nigerian now having moved to I Granata on a permanent basis for £9m (€10m).

What looked like to be four going down to potentially two (considering Alonso’s status), Castillo’s U-turn now means that Chelsea once again has three players vying for the left-back position come next season and going forward, with Alonso still expected to leave this summer.

The left-back situation appears to be taking shape at Chelsea, with the likes of Jay Dasilva and Juan Castillo to be challenging Emerson over the next few seasons

This is all hypothetical of course, but if we take into consideration what is happening to the likes of Dasilva, Castillo and Alonso (now that Aina has left the club permanently), this could leave Chelsea with the possibility of…

– Emerson becoming the main first-team LB.
– Dasilva comes back from loan at Bristol City & becomes the squad LB (back-up to Emerson essentially).
– Castillo goes on loan for a season (or two); challenging Dasilva as back-up LB or perhaps to be utilised more in an LM/LW position.
– Alonso to be sold to Atlético Madrid.

(UPDATE – Jay Dasilva officially re-joined Bristol City on a permanent basis for an undisclosed fee on a four-year deal)

So… Castillo to now feature for Chelsea during pre-season? Challenge for a squad spot now even?

The situation at the left-back position is about to get interesting…

Terry Sazio

What are your thoughts on positive u-turn? Let us know via our official Twitter and via Terry’s personal Twitter as well.