Chelsea ‘bomb squad’, Enzo Fernandez and Joao Felix in ranking of 22 Todd Boehly mistakes

Todd Boehly rode in as Chelsea’s white knight in May 2022 and the poor billionaire’s had a rough time of it since.
Before we get a bunch of “Actuallys” pointing out that Boehly’s influence has waned and he’s no longer be fully involved in the day-to-day at Stamford Bridge, we are aware, but he was the sporting director when we first started this list (more on that nonsense later) and the buck stops at the top.
It should probably be ‘Todd Boehly and Behdad Eghbali’s mistakes’ but the latter has had the good sense to hide behind his business partner, who was all too eager to put his head above the parapet early on.
Anyway, we’ve ranked the many mistakes that have been made under the new owners at Stamford Bridge from minor to major.
22) Premier League All-Stars
Starting a pitch by claiming the Premier League could “learn a lesson from American sports” was never going to go down well, and Boehly’s suggestion of a North versus South All-Star game was predictably met with xenophobically tinged responses from people who Know English Football.
It appeared to be an offhand comment made with the best intentions of giving back to the football pyramid, but the one extra game in the calendar that, let’s face it, loads of people would watch and would provide millions of pounds for smaller clubs was a terrible idea as everyone would definitely get injured during that one specific, half-arsed game.
21) The Mohamed Salah, Kevin De Bruyne academy
At that same New York conference in September Boehly claimed Chelsea have “one of the best academies in the world”, which is arguable, but using Salah and De Bruyne to evidence the worth of that academy rather sullies the argument, and by association any other point about Chelsea or football in general.
Salah broke through at Egyptian side Al Mokawloon before moving to Basel, while De Bruyne made the first team at Genk before a transfer to Chelsea. And namedropping either of those two players to attest to Chelsea’s excellence in developing stars is unwise.
Using Boehly’s earlier All-Star comments against him, Thierry Henry advised the American owner to “learn your own lessons and then come back and teach us something” in reference to his lack of knowledge on the history of his own football club.
20) ‘Disrespecting’ Benfica over Enzo Fernandez
All’s well that ends well, right? Well, Chelsea did get Enzo Fernandez but aren’t now on the best of terms with Benfica, who will no doubt have a player or two they’ll want in the future.
Benfica boss Roger Schmidt wasn’t at all happy with Chelsea’s approach for Fernandez. Referred to as “the club who wants Enzo”, like they’re a footballing Lord Voldermort, Chelsea were accused of making the midfielder “crazy” through suggesting they would meet his £106m release clause, then not doing so, before meeting the Portuguese club’s demands in the end.
19) Not pushing harder for Anthony Gordon
Full disclosure, when we did this ranking back in May 2023 this was still titled ‘Pushing for Anthony Gordon’, but he’s made us all look a bit daft, fully deserved his nomination for the Young Player of the Season and is now being heavily linked with a move to Liverpool for around twice what Chelsea would have paid for him.
MORE ON CHELSEA MESS FROM F365:
👉 No sympathy for Enzo Maresca; he signed up for the Chelsea threshing machine
👉 Only two Chelsea players more annoyed than first Arne Slot outcast in ranking of the 110
👉 Mailbox amused as Chelsea doing ‘Boy Math’
18) Dressing room faux pas
Football is arguably too precious about dressing rooms. While American sports allow journalists and fans into their ‘inner sanctums’, footballers and managers appear to want some sort of DBS check for anyone thinking of setting foot in the holiest of all places.
The Chelsea players were ‘taken aback’ when Mykhaylo Mudryk and his entourage were granted entry with Booehly ahead of the Crystal Palace game back in January, but actually it sounds entirely reasonable to introduce a new signing to the players before a game.
However, attempting to bring a group of guests and their children, with no particular affiliation to Chelsea, into the dressing room at half-time in a Premier League game, is a bold move, not least because bringing children into a dressing room with adult men, who could be changing, could be swearing, could be doing anything, feels all wrong.
Thomas Tuchel told Boehly to do one, and was sacked four days later.
17) ‘Embarrassing’ rant
We don’t know everything about what happened, but what we do know is he called the players “embarrassing”, singled a senior player out for criticism leaving them ‘disillusioned’, and at least one onlooker thought it was “weird”. It doesn’t sound great.
Arsene Wenger reckons any new Chelsea manager, and there have been plenty in the last two years, should have an anti-Boehly clause inserted in their contract. It appears that clause is already in place for the sport of football as a whole.
16) Outsourcing medical work
To be fair, dismissed pair Paco Biosca and Thierry Laurent weren’t doing a great job as medical chief and head physio – Chelsea topped the injury count in the Premier League in 2021/22 with 97 according to Howden’s European Football Injury Index. But the injury problems have ramped up significantly since Boehly decided to outsource some of the medical work to a private physiotherapy company.
Denis Zakaria, Reece James, Raheem Sterling, N’Golo Kante, Wesley Fofana, Ben Chilwell, Armando Broja, Ruben Loftus-Cheek, Christian Pulisic, Edouard Mendy and Thiago Silva all spent significant time on the sidelines in 2022/23, and we barely saw James, Romeo Lavia or Christopher Nkunku last season, with Marc Cucurella, Ben Chilwell, Carney Chukwuemeka, Trevoh Chalobah and Benoit Badiashile also out for a big chunk of the campaign.
In a leaked private message in which he explained why his client and his teammates were struggling due to a ‘lack of pilates and terrain work’, Chalobah’s personal trainer said it best: ‘It’s an absolute mess at the moment, bro.’
15) Signing Pierre-Emerick Aubameyang
Given we were told by Boehly that the club’s decision to sack Tuchel was made over a stretch of time and not as a result of the defeat to Dinamo Zagreb, how the hell can he explain the signing of Aubameyang? He was a 33-year-old striker, who was infamously kicked out of Arsenal for being a bad influence in the dressing room, signed purely because he scored a load of goals under Tuchel eight years ago.
With his transfer fee and annual salary taken into account, Aubameyang cost Chelsea roughly £20k per minute played. He then went on to score and assist a bucketload for Marseille, because of course he did.
14) Failed hijacks
When this list was first published in January 2023 this section was also titled ‘failed hijacks’ as we questioned why the result of cherry-picking people that we assumed were among the best in the business from Brighton, RB Leipzig and elsewhere to oversee all things transfers, those individuals appeared to be engaging with the market in the same way anyone with an interest in football with access to the interweb might – gossip columns.
And although we very quickly had egg thrown in our face as Mykhaylo Mudryk did in fact end up hog-tied and brought to Chelsea over Arsenal, it remains a ‘failed hijack’ by virtue of the impact of said individual. Arsenal got Leandro Trossard, who’s been brilliant, while Mudryk has – save for brief snippets of Shakhtar-like quality – resembled a lost puppy and shoots as though his right foot is made of sweaty salami.
Good thing Boehly’s tied him down for eight years, and then added took up the option of a further year in the midst of his terribleness.
13) Not buying a proven striker
We love Nicolas Jackson, and at £32m he’s been a decent signing, but to spend just six per cent of £1bn on strikers makes no sense at a club that’s been in dire need of a goalscorer since Diego Costa left over six years ago.
12) Signing Joao Felix
A super talented, mercurial forward who can play on either wing or down the middle signed for £42m having cost Atletico nearly three times that much five years ago. It sounds pretty good, but it may well be the most laughable signing of all in a hugely amusing field.
He was quite clearly just a tool for Chelsea to earn pure profit through the sale of Conor Gallagher (we’ll get to that sh*tshow). They actually wanted Samu Omorodion, who may not have the quality and repute of Felix but at least provides something different and useful to Chelsea.
You couldn’t pick a player Chelsea are less in need of than Joao Felix, who has already played for the club lest we forget, in a distinctly average loan spell punctuated by missed chances and frustrating quality, in that it came to nothing nine times out of ten. They’ve already got plenty of players to deliver on those counts.
11) Performance-related contracts
It’s one of those things that sounds far better than it actually is. It seems reasonable to pay players in a team according to how well that team has done. A big problem is that some players are negatively affected by the team’s poor performance and others – those with their wages assured – are not. It caused significant issues in the dressing room last season.
And although this new system hasn’t seemingly been an issue so far in the transfer market, given Chelsea aren’t in the Champions League next season, a similarly big club with a secured pay packet will surely hold the advantage this summer and for as many transfer windows as it takes for the ‘project’ to be realised.
10) Re-apppointing Frank Lampard
It didn’t really matter, but let’s be clear, re-hiring Lampard was completely f***ing mental. To think all that group of players needed was a pep-talk from a club legend perfectly illustrates how deluded Boehly is. 11 games, one win, eight defeats.
9) Selling Conor Gallagher
Can anyone think of another example of a top football club forcing their de facto captain into a transfer? Possibly if that player’s been a bit of tit or they’re passed their best, but other than that we doubt it, because it’s ridiculous.
Add to that the fact that he was Chelsea’s best player other than Cole Palmer last season, has been at the club since he was a wee boy and is being sold for £20m below market value and it’s one of the most ridiculous decisions in football.
The two-year contract they offered – presumably just do they could say they tried – is insulting and we’re glad Gallagher told them where to go. Who would want to play for a football club like that anyway? Fingers crossed he tears it up at Atletico Madrid and shoves it in their faces.
MORE ON CHELSEA MESS FROM F365:
👉 No sympathy for Enzo Maresca; he signed up for the Chelsea threshing machine
👉 Only two Chelsea players more annoyed than first Arne Slot outcast in ranking of the 110
👉 Mailbox amused as Chelsea doing ‘Boy Math’
8) Raheem Sterling and the ‘bomb squad’
“I am not working with 42 players. I am working with 21 players. The other 15-20 players are training apart. I don’t see them. It’s not a mess like it looks from outside. Absolutely not. They can even have 20 years contract, it’s not my point. I don’t care.”
The Chelsea manager there, literally saying he doesn’t give two sh*ts about half of Chelsea’s senior players, including Raheem Sterling and Ben Chilwell, both of whom have been told to find new clubs.
We get that Maresca can’t work with 42 players – a bulging squad was one of the key contributors to Graham Potter’s downfall – but it’s an extraordinary thing to say. What happens if (when) they can’t find buyers for all of those players? Sterling’s on £325,000 per week. He’s going to play for the reserves, is he?
And what a d*ck move to play him for the whole of pre-season, tell reporters how “important” his experience and quality is to the squad, and then tell him he’s not going to play and needs to find a new club with just over a week left of the transfer window. Just a horrible thing to do to him and everyone else in the ‘bomb squad’.
READ MORE: Ranking all 110(!) players left out of opening Premier League matchday squads by how p*ssed off they can be
7) Hiring Graham Potter
Let’s not claim now that is wasn’t an exciting appointment. Potter could have been the man to usher in a new dawn at Chelsea. And yet, in his bid to be nothing like Roman Abramovich, Todd Boehly has been more Roman Abramovich than the Russian oligarch himself, sacking managers with greater regularity than the man whose absolute favourite thing was to swing the axe.
Boehly was said to be surprised by the strength of the fans’ anger at Chelsea’s performances under Potter, and realised that he had no choice but to show him the door with his own relationship with the fanbase at risk. He has of course f***ed that relationship up now anyway.
Hired after pre-season, Potter was handed a poorly balanced and bulging squad featuring a combination of very young players and those that were entirely disillusioned with the club. It was never going to work.
6) £1bn on what?
They ended up doubling their initial offer for Wesley Fofana, eventually landing him for £75m, £88m on Mudryk, £106m on Fernandez, £115m on Caicedo and over £1bn in total on players, very few of whom have so far proved to be worth anywhere near their various, generally exorbitant, transfer fees.
5) Appointing himself as sporting director
Absolutely ridiculous. A guy who had pretty clearly barely watched a game of football in his life became the authority on all things football for one of the biggest clubs in the Premier League. It would be like someone with no experience in education buying a school and making themselves headteacher, hiring and firing teachers, conducting lesson observations and giving feedback.
It’s been a bizarre and scattergun approach to recruitment in general in their time as owners, but that first window when Boehly was heading up transfers was particularly woeful and not in keeping with what we’ve seen since.
Wesley Fofana, Marc Cucurella, Raheem Sterling, Kalidou Koulibaly, Carney Chukwuemeka, Cesare Casadei, Pierre-Emerick Aubameyang and Gabriel Slonina arrived and all but Fofana and Cucurella have either already been sold or are currently being pushed from the club.
Boehly sacked himself midway through the January transfer window having added Andrey Santos and David Datro Fofana to his roster.
4) Sacking Thomas Tuchel
“It wasn’t a decision that was made about a single win or loss, it was made about what we thought was the right vision for the club.” It’s a shame Boehly’s vision couldn’t include the manager who had won the Champions League a year previously and had taken Chelsea to six finals. It’s also a shame Boehly’s vision wasn’t apparent before he spent £270m on players for the manager he would then sack five days after the summer transfer window closed.
Simon Jordan reckons the secret reasons behind Tuchel’s Chelsea sacking would “make people’s eyes water” but on the face of it – even given his struggles at Bayern – the decision looked incredibly rash, and the timing downright ridiculous.
3) Captain Enzo Fernandez
We were told everything’s fine after the Argentinian’s racist chant but we don’t know how it can be. The club has essentially brushed it under the carpet and the offended parties have been told to lump it or leave. Why? Because Enzo Fernandez cost £107m.
Not only do Wesley Fofana and his teammates have to put a brave face on things and accept Fernandez’s return, they now also have to be OK with him being their captain. Enzo Maresca thinking that his namesake acts as an example for others to follow weeks after he filmed himself smiling and singing racist slurs is wholly deplorable.
This is very much beside the point, but he shouldn’t be in Chelsea’s best team anyway.
READ MORE: Enzo Fernandez and Wesley Fofana bring out football’s inhibited racists
2) Sacking Mauricio Pochettino
Reports suggest Todd Boehly was actually happy to keep Pochettino and it was co-owner Behdad Eghbali who was ‘lukewarm’ and pushed for his exit, so this is more a Clearlake mistake than one that rests on Boehly.
Anyway, onto the ludicrous reasons for his departure. Apparently they were ‘concerned by Pochettino’s tactics’ and his ‘antiquated’ training methods, which given as of two years ago these owners had next to no knowledge of football whatsoever they must have swatted up impressively in the meantime.
Perhaps they didn’t see the relationship Pochettino has built with the players, his work on the training pitch and in one-on-one chats coming to fruition. Literally everyone else did. There won’t have been a single rival fan, who will have had growing concerns that the Chelsea sh*tstorm might be about to abate to make way for a sensible and dangerous football team, that didn’t punch the air with glee at the club heading right back to square one under a manager that the majority of the players clearly don’t want because they want the man that’s just been shown the door.
The owners also ‘expected quicker progress given the significant investment on players’, which is unreasonable as they bought children even before you pair that grievance with another reason for Pochettino leaving being because the owners denied his request to be more involved in signing players. Essentially they spent loads of money on players Pochettino didn’t want, and that’s his fault.
What they want is a yes man, and no half-decent coach is going to be that at Chelsea because they can’t trust the people above them to make the right decisions. They had an experienced coach in Tuchel, who pushed back and got sacked, hired a young gun in Graham Potter, who couldn’t hack it and got sacked, hired an experienced coach in Pochettino, who pushed back and got sacked, and now they’ve got another up-and-comer like Potter, who will presumably be on this list as a terrible appointee within six months.
After Enzo Maresca it will be Diego Simeone, and so on and so on until they run the club into the ground.
MORE ON CHELSEA MESS FROM F365:
👉 No sympathy for Enzo Maresca; he signed up for the Chelsea threshing machine
👉 Only two Chelsea players more annoyed than first Arne Slot outcast in ranking of the 110
👉 Mailbox amused as Chelsea doing ‘Boy Math’
1) The FFP mess
Nothing sums up Todd Boehly’s time at Chelsea quite like them not being able to afford to play in the Europa Conference League. Reports earlier this year suggested they would rather be banned from European competition than enter its third tier as they’ve spent so much money that they couldn’t afford the financial hit of playing under UEFA’s stricter financial rules.
Fortunately, the lads have come up with the ingenious plan to ensure they will meet Servette, the third best team in Switzerland, in the ECL play-off on Thursday. Phew.
They’re selling all of their delicious ‘pure profit’ players, otherwise known as the academy graduates, who grew up in and love the football club, but have big fat Euro symbols floating over their heads.
Boehly’s already got rid of Mason Mount, Ruben Loftus-Cheek, Ethan Ampadu, Callum Hudson-Odoi, Lewis Hall, Billy Gilmour, Ian Maatsen and Conor Gallagher, have very nearly seen the back of Armando Broja and are doing everything possible to send Trevor Chalobah on his way. So much for soul and identity.