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Chelsea need a reality check...

The 10 most expensive transfer windows in history: Chelsea, Real Madrid, Barcelona…

Inflation and transfer fees becoming increasingly silly in men’s football has meant that we as fans have witnessed some truly absurd transfer windows on cost alone.

We’d say that transfers have gone beyond the point of no return in the era since Neymar was sold to Paris Saint-Germain for a world record £200million, but the numbers since have been so unsustainable that clubs are inflating players’ values and simply unable to keep up with the inflation, thus the market is bound to crash at some point.

Before we reach that next level of absurdity, though, we’re taking a look at the 10 most expensive transfer windows put together by specific clubs in the history of men’s football so far, thanks to figures from Transfermarkt. Strap in and be prepared to cry quietly into a pillow after reading through unfathomable sums of wealth…

10. Manchester City (2017-18)

In the summer of 2017, ahead of the 2017-18 campaign, Manchester City spent a colossal €249million according to Transfermarkt, which at the time equated to £213.8m.

After Pep Guardiola’s side finished a lowly third in 2016-17, the oil-rich club pulled the chequebook out for the iconic manager ahead of his second season in charge and presented him with a mini-war chest to rebuild the squad.

They signed eight players in total: Ederson, Bernardo Silva, Kyle Walker, Benjamin Mendy, Danilo, Douglas Luiz, Luka Ilic and Ivan Ilic. Looking back seven years on, ‘money well spent’ would be a stretch, but at least they got three key first-team players out of it who have been crucial ever since.

9. Real Madrid (2009-10)

It’s unsurprising that Real’s 2009 summer window makes the list, considering it’s the summer where they finally prized Cristiano Ronaldo away from Manchester United for a then-world record £80million.

Los Blancos spent €259million in total that summer, also signing: Kaka, Karim Benzema, Xabi Alonso, Raul Albiol, Alvaro Negredo, Esteban Granero and Alvaro Arbeloa. Outrageous.

Like City, Real put down a war chest, but were able to do so in a time before Financial Fair Play (FFP) and – crucially – secured their legacy over the next decade as European powerhouses. They’d do it all over again if they had to.

8. Juventus (2018-19)

After Real were done with Ronaldo just shy of a decade later, they managed to sell him for a profit to Juventus, who paid £99.2million to sign the forward in the summer of 2018.

Bored of domestic dominance and having come agonisingly close to European glory in previous seasons, the Old Lady broke the bank in a transfer window that set them back some €265million in the summer of 2018, which they hoped would be the final step towards a first Champions League since 1996.

Along with Ronaldo came a further seven players including the likes of Joao Cancelo, Douglas Costa and Leonardo Bonucci. Plenty of star power, but it all came crashing down shortly after as they failed to win the Champions League, dropped away from the top of Serie A and ended up in a tight financial spot.

7. FC Barcelona (2019-20)

Barcelona’s spending in the summer of 2019 goes a long way in explaining a lot of the financial turmoil they still find themselves in five years on.

Antoine Griemann was the star signing that summer, joining the club from Atletico Madrid after La Blaugrana activated a £107million release clause in his contract – only to get lost in the shuffle and look a spare part in a side where Lionel Messi occupied his best position.

That about sums it up, with Barcelona spending €279million/around £235million that summer, only for the club to completely implode at the end of the season during the early stages of the COVID-19 pandemic, crashing out of the Champions League and then tumbling into mini-turmoil in the years since.

6. Chelsea (2022-23)

Spoiler – this is the first of three Chelsea appearances in this list. Yeah, three. Seriously.

In the first summer under the new ownership of Todd Boehly and Clearlake Capital, Chelsea splashed €301million in total, equating to in excess of £250million, on a whole host of players.

Key signings included the £72million signing of Wesley Fofana – who has since spent two seasons out with serious knee injuries – the £58million signing of Marc Cucurella, £50million on Raheem Sterling and £34million on Kalidou Koulibaly, who was sold after just one season.

5. Chelsea (2022-23)

How do you go one further than one of the most batsh*t crazy first summer transfer windows in charge of a club as new owners? Easy – keep the spending going that same winter.

As if new manager Graham Potter didn’t already have enough pressure on him by inheriting a seriously inflated and mightily expensive squad in September 2022, they ramped up the pressure some more by spending around €330million in the winter window.

Mykhailo Mudryk was expected to sign for Arsenal before Chelsea swooped in with a successful £88million offer, while also signing Enzo Fernandez from Benfica for £105million and Benoit Badiashile for £35million – among others.

In total, Chelsea wound up spending £747million on transfers in the 2022-23 season, with their wage bill rising 18% to £404million. In one season.


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4. Real Madrid (2019-20)

A rare misstep for Real and one they have undoubtedly learned from in the time since, Eden Hazard’s failed transfer which cost an initial £89million, but could’ve been worth £150million with certain add-ons.

Los Blancos spent €331million that summer, to varying degrees of success. Rodrygo and Eder Militao have proven to be hits, as has Ferland Mendy, but Luka Jovic underwhelmed massively.

3. Paris Saint-Germain (2023-24)

Tasked with replacing Neymar and further freed up by Lionel Messi also coming off the wage bill, PSG splashed their oil-rich cash in the summer of 2023 in a bid to rebuild their squad, spending an eye-watering €350million.

In came Randal Kolo Muani from Eintracht Frankfurt for £76.4million in total, while they also splashed on Ousmane Dembele, Manuel Ugarte, Lucas Hernandez and more.

It’s too early to judge how successful a window it has been with Les Parisiens spending more on younger talent, but one would hope that the return is rather instant from this season.

2. Al-Hilal (2023-24)

It wouldn’t be a football spending list without a Saudi Pro League side. Al-Hilal contributed to PSG’s spending that summer by handing them an initial £86million for Neymar, in a summer that cost them €353million/just shy of £300million.

Desperate to try and continue to pull top players out of the European game, Neymar wasn’t Al-Hilal’s only big-money investment. They signed Sergej Milinkovic-Savic from Lazio, Ruben Neves from Wolves, Aleksandar Mitrovic from Fulham and took Kalidou Koulibaly off Chelsea’s hands after his one difficult season in England.

Neymar unfortunately ruptured his ACL after just five games for his new club, but it didn’t stop them from winning the Saudi Pro League, finishing 14 points clear of runners-up Al-Nassr.Jordan Henderson of Al Ettifaq

READ: Six star players who have already left the Saudi Pro League in 2024

1. Chelsea (2023-24)

Complete absurdity. Off the back of a season that saw them spend a seriously concerning £747million on transfers, Chelsea went and spent €464million/£435.5million.

To partner £105million midfielder Fernandez, Chelsea spent a British-record £115million to hijack a deal Liverpool had already agreed for Moises Caicedo. Chelsea also signed Romeo Lavia and Lesley Ugochukwu to seemingly stockpile talent for the most expensive midfield ever, in a truly ridiculous summer splurge.

Christopher Nkunku was expected to be the star signing in attack, but that changed when they signed Cole Palmer from Manchester City in a £42.5million deal. He immediately silenced all doubters, bagging 22 goals and assisting 17 to win the Premier League Young Player of the Season award, as well as Chelsea Player of the Season.