Todd Boehly's 13 worst signings at Chelsea (ranked)

Chelsea have become something of a laughing stock over the last few years, with their approach to transfers bordering on farce, having spent hundreds of millions of pounds and been through several managers in the short two-year period since Todd Boehly’s consortium took over.

Their unrivalled extravagance in the transfer market has not been matched with success on the pitch, with the vast majority of the circa-£1bn spent in that time set to go down the proverbial drain. Put simply, there have been far more misses than hits.

At the time of writing, nine new signings have been brought in by Enzo Maresca – the third permanent manager to be appointed during the Boehly/Clearlake era. While most of those signings can yet claim to be among the worst arrivals in recent times, the odds are hardly in their favour given the current hierarchy’s poor success rate when it comes to buying players.

With that in mind, we have come up with a list of Chelsea’s worst post-Roman Abramovich deals so far. For this list, we’ve considered players’ performances, the fee they were bought for, and the amount of sense a deal made – whether from a financial or sporting point of view. Of course, this is all subject to change…

13

Robert Sanchez

£25m from Brighton, 2023

After selling Edouard Mendy to Saudi Arabian club Al-Ahli, Chelsea were in need of a new No 1. Their decision to replace the Senegalese shot-stopper with Spaniard Sanchez was not necessarily a bad one given its necessity, but few could argue that it has worked out for the best.

Sanchez wasn’t even assured of his starting place heading into the new season, though he was named in Chelsea’s opening-day defeat to Manchester City in Enzo Maresca’s first game in charge.

He has failed to make the No 1 position his own despite his apparent lack of top-quality competition, though given the errors he has made, it could be considered that is more down to the player rather than the backroom team.

That said, allowing Kepa Arrizabalaga to move on in the same summer hardly seemed wise, while the fact two more goalkeepers have been signed since points to a total lack of direction.

12

Omari Kellyman

£19m from Aston Villa, 2024

Of course, there is no blame attached to Kellyman himself here. A cynic could even say the owners were genuinely acting in the club’s best interests by signing the Aston Villa youngster for £19m in order to bypass concerns over the Premier League’s profit and sustainability rules.

But of course, the very fact that Chelsea were in any sort of PSR predicament will have been directly down to their spending habits.

And given the vast sums of money spent over the last few years (not limited to the players on this list, nor even the Boehly regime – remember Lukaku?), Kellyman’s pricey arrival is a damning indictment not only on modern football but Chelsea’s financial mismanagements.

11

Wesley Fofana

£70m from Leicester, 2022

Another one where you couldn’t squarely place the blame on the ownership, but Wesley Fofana’s Chelsea career has been an unmitigated disaster.

We’ll give the owners the benefit of the doubt, but they certainly haven’t had the best of luck, with Fofana making just 20 appearances before the start of this season, having missed the entirety of the 2023/24 campaign.

While Fofana’s luckless injury record is far from the owners’ fault, his transfer has still been a colossal waste of money thus far. But with the Frenchman not turning 24 until December, there is plenty of time to turn things around.

10

Malo Gusto

£30.7m from Lyon, 2023

Malo Gusto is one of several Chelsea arrivals who have yet to reach their potential. Given he’s only 21, there is plenty of time for the Frenchman to become a true superstar and render his £30.7m transfer fee a bargain, but the decision-making process is what makes this move a bold one.

Nine assists in all competitions demonstrate a creative side from the full-back, though his ill-discipline was also on show, collecting seven yellows and a red in his only full season to date.

He has also been thrust into first-team action amid Reece James’ injury struggles, though the fingers can again be pointed at the ownership here – was spending so much on an understudy to one of the Blues’ best players (when fit) the best plan at a time he desperately needs games?

James’ fitness concerns have instead turned out to be a blessing for Gusto’s career, so here’s hoping he can make the most of his opportunity in the new campaign (sparing Boehly’s blushes in the process).

9

Axel Disasi

£38.5m from Monaco, 2023

Despite scoring on debut against Liverpool last season, Axel Disasi can hardly claim to be the rock at the back Chelsea need – particularly amid the exit of Thiago Silva in the summer.

It would be harsh to pin the brunt of the blame at the centre-back’s door – he has shone on occasion – but for such an outlay on a defender who will be one of the more experienced heads in the Chelsea squad at 26, it could be argued that the Blues are yet to see a return on that hefty fee (which is no fault of the player’s, of course).

He was a trusted member of the squad under Mauricio Pochettino – he played 44 times in all competitions – but was nevertheless part of the worst defence in last season’s top eight.

One could argue that Pochettino’s exit and the likes of Trevoh Chalobah being banished from the first team – both decisions from up top – risk undoing Disasi’s progression to this point and putting too much pressure on him to come good for a team that is lacking in cohesion amid all the changes at Stamford Bridge.

8

Pierre-Emerick Aubameyang

£10.3m from Barcelona, 2022

Given the aimless spending since their takeover, one of the more left-field signings from Chelsea was that of Pierre-Emerick Aubameyang. Having previously left rivals Arsenal under a cloud after losing the captaincy there, the Gabon striker signed from Barcelona, where he seemed to rediscover his scoring touch.

However, that appeared to vanish once he returned to London. While hardly an obscene waste of money, it was most certainly a waste of time; a return of 3 goals in 22 games would hardly have been what Boehly and co were after.

But again, the owners aren’t completely blameless. They fired Thomas Tuchel just five days after signing Aubameyang, with successor Graham Potter limiting him to cameo showings off the bench as Auba’s Premier League comeback fell flat.

7

Raheem Sterling

£50m from Man City, 2022

Handing a league rival £50m isn’t common – in fact, Chelsea were the first to do it in 2011 – but in this case, Manchester City were surely laughing all the way to the bank.

Raheem Sterling had not long been the star of England’s Euro 2020 campaign, but he had seen his chances at City dwindle despite their successes, with the arrival of Jack Grealish providing a strong challenge to his starting position.

Perhaps few could begrudge Chelsea for jumping on the opportunity of bringing Sterling to Stamford Bridge, but with plenty of iffy transfer market decisions being made, the Blues really could have done with a hit here.

Instead, Sterling has failed to assert himself at Chelsea, and is now on the way out following Enzo Maresca’s arrival. It will end a rather pitiful period for the winger, who notched 14 times in the Premier League in two seasons – just one more than in his final City campaign.

6

Enzo Fernandez

£107m from Benfica, 2023

It’s the golden rule of a transfer window: never buy anyone purely off the back of a World Cup. But in early 2023, that’s exactly what Chelsea’s so-called transfer experts appeared to do when signing 21-year-old Enzo Fernandez, not to mention for a then-British record of £107m.

Clearlake’s penchant for long-term investments has arguably not been epitomised more than in the arrival of the Argentinian, who has failed to set Stamford Bridge alight since his nine-figure switch.

Despite this, he has featured heavily in a rare show of stability, if not a show of talent. For over £100m, one would surely expect Fernandez to be in the running for the Young Player of the Year award as a prime up-and-coming talent, but Chelsea’s only representative in that regard has been a City academy product bought for less than half that price.

For a club seemingly out of control when it comes to finances, they’re not even close to at least getting some success to justify their outlays.

5

Benoit Badiashile

£35m from Monaco, 2023

Having been at Chelsea for 18 months, Benoit Badiashile ought to have a longer list of accomplishments than he can currently claim. The Frenchman arrived in January 2023 on a seven-and-a-half-year deal, but didn’t exactly hit the ground running.

His performances have been slated, while he has only featured invariably for Chelsea. Injuries have played a part in this, but their inflated squad could also be to blame – despite being bought by Graham Potter (or rather, during his tenure), the centre-back was left out of the Blues’ Champions League squad ahead of the knockout stages in 2022/23.

Having yet to deliver in Chelsea colours despite all his promise, he is pretty much a living encapsulation of what the club has become under the Boehly regime.

4

Joao Felix

Loan and £45m from Atletico Madrid, 2023 & 2024

This is Boehly’s Chelsea doing Boehly’s Chelsea things. Loaning Joao Felix from Atletico Madrid in early 2023 was intriguing enough – not least after he managed to get himself sent off on his debut.

His comeback didn’t see him installed as a first-team regular, with little to speak of his brief time in blue before returning to the Spanish capital, where he continued to be unsettled as he was shipped off to Barcelona for a year. It was a brow-raising deal, to say the least.

Then, amid all the chaos of being seemingly desperate to offload one of their finer academy products in recent years (no, not Mason Mount), Chelsea rather inexplicably turned to a familiar face after failing to sign Samu Omorodion – a striker – in order to allow Conor Gallagher to leave.

Having apparently disrespected the youngster during contract negotiations, deals for him and Gallagher looked off, even forcing the midfielder to return to training at Cobham, where he was clearly no longer wanted.

Joao Felix – not a striker – recently secured a return to Stamford Bridge, almost purely to get Gallagher off the books. So now the Blues are a midfielder light, have spent over the odds (Atleti have netted a sizeable profit over these deals) and have a player who they know was previously underwhelming. Confused? Good – so are we.

3

Nicolas Jackson

£32m from Villarreal, 2023

When signing young players, it’s difficult to know who’s to blame when things don’t immediately catch fire. Mauricio Pochettino certainly backed his signing to come good, and let’s not forget Chelsea are now a Europa League-level outfit (at best) – so 17 goals in all competitions isn’t too shabby for Nicolas Jackson’s first year.

But with Pochettino out of the picture and Chelsea snooping around for new strikers, who knows what the future holds for Jackson? The player has to take his share of the criticism coming his way, too – his form fluctuated throughout the 2023/24 campaign, though he did enjoy a late flurry of goals as the Blues hit their stride.

Unfortunately, unless Jackson just happens to become a world-beater overnight, this has all the hallmarks of another transfer failure. Whether Joao Felix or a future arrival will affect the Senegalese’s first-team prospects remains to be seen, but it doesn’t exactly appear as though Maresca is his biggest fan.

All this means is the owners’ rather needless decision to sack Pochettino has all but doomed yet another big-money punt to failure.

2

Mykhailo Mudryk

£89m from Shakhtar Donetsk, 2023

It wasn’t too long ago that £89m bought you the best players in the world. In one of the clearest signs of proof that transfer prices have gone out of control, that sum has bought Chelsea the net sum of, well, not very much at all.

You’d be a brave one to argue that Mykhailo Mudryk either has been or will be worth the money, with the Ukrainian flattering to deceive after shining for Shakhtar Donetsk prior to his Stamford Bridge move.

If making the wrong call on Mudryk wasn’t humiliating enough, his move came in almost complete contrast to Leandro Trossard’s, as Arsenal turned to the winger after being beaten by Chelsea to Mudryk’s signature. The Gunners went on to move for the 18-goal Belgian and ex-Blues man Kai Havertz for a combined £92m – money spent far more wisely given their respective outputs in north London.

As with many players on this list, time is on Mudryk’s side to transform his fortunes at Chelsea, but his price tag means the heights he has to reach are quite frankly enormous.

1

Moises Caicedo

£115m from Brighton, 2023

In August 2023, Chelsea broke the British transfer record to sign Moises Caicedo from Brighton. For all of the chaos that the Boehly regime has endured, the fact the Blues have the ability to win transfer battles over the likes of Liverpool is commendable.

However, the overall strategy when it comes to team-building has been exposed. Caicedo is a fine talent for sure, but his failure to assert himself as one of the league’s best players points towards the environment at Chelsea being sub-optimal. There are so many ‘flops’ arriving at Chelsea, the club surely has to be the root cause.

Sacking Pochettino has added another layer of ‘what if?’, especially as he’d left the club with just 1 defeat in 15 league games – and as one of the Argentinian’s key men, whatever hope there was Caicedo has probably been reset following the latest raft of personnel changes at the club.

It is difficult to pinpoint what the purpose is of handing a manager so much money, only to rip everything up and start again – especially just when things looked on the up. In terms of Caicedo specifically, there quite literally has not been a larger waste of money to this point in English football history.