EVERY Chelsea Transfer Under Todd Boehly – Part Two

Last time out, we looked at the first 19 transfers at Chelsea during the Todd Boehly era – today, we’ll be looking at the 21 that still remain.

As before, we’ll only be looking at permanent deals for this list – any transfers that took place on a loan or trial basis will not be considered.

Pedro Neto

Liam Rosenior recently described Pedro Neto as a ‘world-class’ winger – this might be a foray into the realms of hyperbole, but Neto is still an excellent wide man with plenty in his locker.

Signed from Wolves in 2024 for a fee of just under £54 million, he has been a dependable first-team regular for the Blues since his arrival.

Joao Felix

Joao Felix, on the other hand, was not quite so successful in a Chelsea shirt. A fine player from a technical standpoint, Felix could not adapt to the hustle and bustle of the Premier League.

He had previously spent a spell on loan at Chelsea in 2023, to similar results. In total, the Portuguese international made just 12 Premier League appearances during his second Blues stint, scoring a single goal.

Kiernan Dewsbury-Hall

This was a confusing one – Kiernan Dewsbury-Hall had been a fine player at Leicester City, but when Chelsea snapped him up for a reported fee of £30 million, it seemed they didn’t know what to do with him.

After spending most of his time at Chelsea in their B team, he was sold to Everton in 2025 for an undisclosed fee.

Filip Jorgensen

Once considered one of the best young goalkeepers in the world, Filip Jorgensen has yet to stake his claim as Chelsea’s number one.

Since he joined the club in the summer of 2024, Jorgensen has made just eight Premier League appearances – he has largely been relegated to cup appearances.

Omari Kellyman

Omari Kellyman is still with Chelsea, but hasn’t made a Premier League appearance for them as of yet. Currently, he is on loan at Cardiff City in League One.

He has been one of the Bluebirds’ better players this season, scoring five goals amid their promotion charge.

Mike Penders

Mike Penders was signed in 2025, though it was announced that he would join Chelsea in the summer of 2024.

He hasn’t made an appearance for the Blues yet – upon his arrival, he was promptly loan out to affiliate club Strasbourg.

Aaron Anselmino

Aaron Anselmino’s story is similar to Penders’ – he, too, has yet to make his senior debut for Chelsea, despite being at the club since 2024.

During his time at Chelsea, he has spent time on loan at Borussia Dortmund, Strasbourg and previous club Boca Juniors.

Mathis Amougou

Mathis Amougou’s trajectory was similar, yet different to the previous two entries. He made his debut for Chelsea last year, coming on as a substitute against Southampton.

However, shortly after this, Amougou would leave the club to join Strasbourg on a permanent deal in the summer of 2025.

Renato Veiga

Likewise, Renato Veiga also spent just a single season at Chelsea before the Blues opted to cut ties with him in 2025.

A towering central defender, Renato Veiga made seven Premier League appearances for Chelsea before joining Villarreal.

Caleb Wiley

Another player who hasn’t made his senior debut for Chelsea yet, the Blues snapped him up from Atalanta for a fee of £8.5 million.

Since making the jump to Stamford Bridge, Wiley has been loaned out to both Strasbourg in Ligue 1 and Watford in the Championship.

Marc Guiu

Marc Guiu has had a hectic season – at the start of the campaign, he was loaned out to Sunderland, but was recalled just weeks later due to injuries within the Chelsea squad.

His Premier League minutes have been limited, but Guiu has performed a fine job in domestic and European cup competitions this season.

Tosin Adarabioyo

Tosin Adarabioyo hasn’t moved mountains at Chelsea, being used as a backup option in most cases. However, as they signed him on a free transfer, the Blues can’t really complain about this one.

Adarabioyo had been a solid player for Fulham before his jump to Stamford Bridge in 2024, but he has since become lost in the mix.

Joao Pedro

Joao Pedro’s form has been spotty this season, but the Brazilian international is almost unplayable on his best day.

He has seemingly answered the never-ending question to Chelsea’s centre-forward problem – he can also function as a number ten, too.

Jamie Gittens

Jamie Gittens is certainly a work in progress. The attributes are all there – he just needs to put them all together on a consistent basis.

He has shown some serious flashes of brilliance since he joined Chelsea, but given his transfer fee of over £50 million, it’s fair to say that Blues fans expected more than what he has delievered so far.

Alejandro Garnacho

Much of the same can be said about Alejandro Garnacho. After he fell out with the coaching staff at Manchester United and joined Chelsea, he hasn’t really hit the ground running yet.

In the Premier League, he has scored just a single goal and has notched up three assists. Thankfully, at just 21 years of age, he is still very young.

Estevao

Wonderkid Estevao has been one of Todd Boehly’s best signings since he took on the mantle of Chelsea ownership. An exciting, tricky winger, the sky truly is the limit for this young man.

Despite being just 18 years of age, he is already one of the Blues’ most effective wide men, using his pace and dribbling ability to torment defenders.

Jorrel Hato

Jorrel Hato was expected to be a big deal when he arrived at Chelsea, but he has yet to fully materialise for the Blues.

In cup competitions, Hato has often looked fine, but his minutes in the Premier League have been severely limuted due to the string form of Reece James and Malo Gusto.

Liam Delap

Liam Delap was a shining light for Ipswich amid their dismal relegation campaign in 2024/25. However, this has seemingly been lost in translation following his move to Chelsea.

He has often looked lost on the pitch, failing to take chances or hold the ball up effectively. He has plenty of potential, but like so many others on this list, he has yet to fully realise it.

Dario Essugo

Dario Essugo was signed by Chelsea in March of 2025, with the deal becoming official upon the opening of the summer transfer window.

Sadly, he has spent the entire campaign out of action with a thigh injury – it’s unclear when he will be fit to play.

Mamadou Sarr

Mamadou Sarr joined Chelsea in the summer – after initially making his debut for the Blues at the Club World Cup, he was loaned out to Strasbourg.

Despite being 20 years of age, he quickly established himself as a first-team starter at Strasbourg and was named as their club captain.

Kendry Paez

Kendry Paez has been known to Chelsea fans for several years, but he only made the jump to Chelsea officially in 2025 due to international transfer restrictions on age.

At 18 years of age, he is currently out on loan at River Plate. Previously, he also spent a spell on loan at (you guessed it) Strasbourg.