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Chelsea FC: The Most Embarassing Football Season in History 💰️ 🚽
€760mm+ spent, but their worst PL finish ever.
GM, Free Agents. The weekend is well-nigh here.
Welcome to the The Free Transfer— the 5-min daily newsletter making you smarter about football.
Sorry Chelsea fans. We’ll call this one a “Friday Flogging”. This one will actually take more like 7 minutes to read.

Today’s menu:
Chelsea FC: Was this the most embarassing season in football history? 💰️ 🚽
What happened? 🤷♂️
Who is at fault? 🏃
Where does it go from here? ⏩️
CHELSEA FC: THE MOST EMBARASSING FOOTBALL SEASON IN HISTORY 💰️ 🚽
After being totally dismantled by Manchester United last night, we take a look at Chelsea FC’s historically awful season: from bad to worse to worst.
How it happened
Introducing, Todd Boehly 🆕 🧑💼

After the club was forced to be sold by the British government, it did not take long for Chelsea fans warm up to Todd Boehly. With no football experience, he has attacked the transfer market like that of the sport he knows: baseball.
6yr+ contracts players, trying to trade players, exorbitant amounts of money spent in one season. Soon he will have the fans singing “Take Me Out To The Ballgame”.
The most expensive summer transfer window of all time 💸
Let’s take a look at Chelsea’s summer transfer window, and what they have contributed to the domestic campaign this season. (Source: Fabrizio Romano)
Cesare Casadei
€20mm from Inter Milan. Playing in Chelsea U21s.
Gabriel Sloninan
$15mm from Chicago Fire. Playing in Chelsea U23s.
Dennis Zakaria
€3mm loan fee from Juventus. 5 PL starts.
Pierre-Emerick Aubameyang
€14mm + Marcos Alonso, from Barcelona. 5 PL starts, 1 goal.
Carney Chukwuemeka
£20mm from Aston Villa. 2 PL starts.
Kalidou Koulibaly
€40mm from Napoli. 20 PL starts.
Raheem Sterling
£55mm from Manchester City. 22 PL starts, 6 goals & 3 assists.
Marc Cucurella
£62mm from Brighton. 21 Pl starts, 2 assists.
Wesley Fofana
£75mm from Leicester. 14 PL starts.
Total Spent: €336mm + Marcos Alonso
This breaks the previous single-window transfer record set by Real Madrid in 2019 of €321mm.

Chelsea were declared “winners of the transfer window” & tipped to have a big season.
As “winners of the transfer window” with cult hero coach Thomas Tuchel at the helm, Chelsea looked to be a club that could challenge Manchester City for the Premier League title this season. It didn’t quite turn out that way.
Start→Tuchel sacked 😬
After 3 wins from their first 6 PL matches and a loss to Dinamo Zagreb in the Champions League group stage, Tuchel was sacked by Todd Boehly who insisted they had “differences” in their vision for the club.
Boehly’s decision did not go over well with fans who adored Tuchel after he won the Champions League just 14 months earlier with a floundering squad under Frank Lampard.
Potter appointed 🧙♂️
In the previous few seasons, Graham Potter had played the role of the “up-and-coming” British coach that the Premier League seems to always have. He brought Brighton from relegation to their first top-half finish ever. They were in 4th place in the (albeit early) Premier League table when he got the call from Chelsea. Boehly shelled out more than £21mm to release Potter from his Brighton contract.
When Potter joined Chelsea in early September, Boehly admitted to having an eye on him since the summer as the manager for Chelsea’s “long term project”.
In the early days, the Blues enjoyed a great run of form under Potter from September-October. They picked up a handful of wins in the PL, and dominated their Champions League group. Things went south going into the World Cup break with 3 successive losses to Brighton, Arsenal, & Newcastle.
January: biggest transfer window in history— spent more than Europe’s other Top 4 leagues combined 🤑

And this was before they bought Enzo Fernandez for €120mm…
Chelsea’s winter transfers (Source: Fabrizio Romano):
Joao Felix
€11mm loan fee + €6mm in salary, from Atletico Madrid. 11 PL starts, 4 goals.
David Datro Fofana
€12mm from Molde. 1 PL start, 0 goals.
Andrey Santos
€20mm from Vasco da Gama. Loaned to Palmeiras.
Malo Gusto
€30mm + add ons, from Lyon. Loaned back to Lyon.
Christopher Nkunku
“More than €60m clause” per Fabrizio Romano, from RB Leipzig.
Will join in summer 2023.
Noni Madueke
€35mm from PSV Eindhoven. 6 PL starts, 1 goal.
Benoit Badiashille
€38mm from AS Monaco. 10 PL starts.
Mykhaylo Mudryk
€100mm from Shakhtar Donetsk. 7 PL starts, 0 goals & 2 assists.
Enzo Fernandez
€120mm from Benfica. 17 PL starts, 2 assists.
Total Spent: €426mm + however much “extra” from Nkunku deal
TOTAL SPENT IN 2022-2023 SEASON: >€765mm 🤑 🤮
But now, back to the actual football being played on the pitch…

Things got rocky for Graham Potter in 2023.
January through February period ❄️
In 12 games played from January to the end of February, Chelsea won 2 games out of 12 in all competitions. Chelsea were in 11th place with 32 points. The football was ugly, the team was not gelling, and Potter seemed to be completely out of ideas.
Although he constantly spoke to the media about how Potter was their coach for the long-term project, Boehly needed results after spending the most money in history— two transfer windows in a row.
March → Potter sacked 💼
Ahead of the March international break, Chelsea picked up a few PL wins, and advanced to the UCL quarterfinals after beating Dortmund. All of that, only to draw an abysmal Everton side at home going into the international break. After the break, a loss to Villa & a 0-0 draw with Liverpool (both at home) were the straws that broke the camel’s back.
Todd Boehly mercifully sacked Graham Potter on April 3rd. The job always seemed a bit too big for him from the beginning. He is a slow-burn type of manager, and he was never going to get that kind of time at Chelsea.
Lampard appointed as caretaker 🙃
The less said about this period, the better. This gig did not boost Frank’s CV.
1 win from 10 matches. Easy eliminated by Real Madrid in UCL quarterfinals 4-0. Currently 12th place but very well may finish the season this weekend in 13th.
So whose fault is it? 🙈 🙉

Just sharing more of our fave Boehly pics.
It’s hard not to point the finger at everyone involved in situations like this, so we will go in order of who is most at fault.
Todd Boehly 💵
Boehly bought Chelsea and was full of good intention. He wanted to invest and make Chelsea into a world footballing super power. To his credit, he definitely did one of those things.
Breaking the record for transfer spend in back to back transfer windows made him popular with the fans. What he clearly did not think about was how a locker room with ~35 senior players fighting for 11 spots on the pitch would have 0 morale.
On top of that— sacking Tuchel so early into the season, replacing him with Potter who had no top-level experience, not giving Potter the time needed to succeed, adding more pressure on Potter & the locker room with huge January spending, etc. The list goes on.
Boehly thought he could outsmart the market, the sport, & the Premier League. He overpaid for most transfers, failed to understand the dynamics of the sport, and his team may have their lowest-ever Premier League finish. He gets most of the blame.
The managers 🔢
Throughout the season Tuchel, Potter, & Lampard have all done a poor job with the resources given to them. Although the were given a poisoned chalice with high expectations due to ungodly spending, the managers did not come close to meeting the standards.
Tuchel abandoned his system that had worked very well in the previous 2 seasons, and would not compromise. Performances & results fell of a cliff.
Potter never seemed to have a system. He seemed to go with whatever seemed to be working, as if he were a manager trying to avoid relegation. He probably always needed a full preseason to instill his ideas.
Lampard was given a job with 0 pressure because there were literally no expectations. He somehow found a way to make it worse. He could have used these past few months to give youth players PL experience, but no.
The players ⚽️
Throughout this season, there has been so much change at the club. This makes it hard to blame the players. That being said, many were bought for huge sums of money & have been shells of their former selves. A blank slate will likely be given for next season, but the players have a debt to repay to the club & fans.
Does it get better from here? 🔭

Can Pochettino resuscitate Chelsea?
Two positives for the offseason ➕
Boehly has stated in the past week that he will step back from his sporting responsibilities at Chelsea. Appointing a real sporting director who understands football would be a huge step forward for Chelsea. Just keep sending that cash, Todd.
Pochettino is a good hire who knows how to get the best out of players, especially young ones. Chelsea shouldn’t need to spend much for him to succeed (relative to this season).
Summer priorities ☀️
Sell as many players who are not in Pochettino’s plans, as possible.
Chelsea will have forty (yes, 40) senior players at the club this summer once players have returned from loan.
The club will need to move on about half of them before thinking about making purchases (loans, sales, contract terminations).
Without any European competition next year, Chelsea shouldn’t need more than ~20 senior players.
Give Pochettino what he needs ⤵️
TLDR;
Chelsea got a new owner who spent more money than any other club have in the history of the sport, but may yet have their worst Premier League finish in their history.
The strategy of “throw money at every player and see what sticks” absolutely killed the locker room & robbed the managers of confidence. Somehow after spending nearly €800mm, the squad still had glaring holes in different positions. This resulted in terrible performances and results.
This summer will be about getting rid of 20 players faster than Todd Boehly can yell “Touchdown!”. Pochettino will need the full preseason to instill his ideas going into next season. He should get all the time needed next season to build the club back up. Right now, that’s looking like a tall order.
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