Chelsea’s transfer strategy: is there method to the madness?

It was a long time since Raheem Sterling had been so excited about a new season. He could not wait to work with Enzo Maresca, at last a Chelsea manager steeped in the football of Pep Guardiola, like himself. He had finished 2023-24 well, scoring vintage goals in two of his last three games. The types Pep would love and Maresca should like: coming in from wide with a dribble to finish.
He was sent on his holidays with words of encouragement from Chelsea’s sporting directors, Paul Winstanley and Laurence Stewart. “Your career here is progressing nicely,” they told him. “Have a good break, come back strong.”
He shortened his annual vacation in Jamaica to begin training for 2024-25 two weeks early and was the first player in on Maresca’s first day. On Chelsea’s US tour he played every game. “For sure, he is one of our important players . . . the important thing is we give him minutes, and he is doing well,” Maresca said.
In the build-up to Chelsea’s opener against Manchester City, the positive indicators continued. The club highlighted his “leadership role” for a piece on their website, headlined: “Raheem Sterling interview: A positive influence and setting standards”. Chelsea made him one of the faces of the club, alongside Millie Bright and Enzo Fernández, in an advertising campaign for a new sleeve sponsorship.
Just one thing nagged him. In training, Maresca didn’t include him in set-piece rehearsals. “Maybe I’m on the bench for City,” Sterling told himself. That would be disappointing, but he could always respect a coach’s footballing decision.
However, two days before the game, Maresca took him aside. More signings were arriving and the weather had suddenly changed. You’re not in the squad and you’ll struggle for minutes this season, the head coach said. Sterling thanked the Italian for his honesty, but left Cobham shocked. Three days later, Maresca told a press conference: “I prefer different kinds of wingers” — just as Chelsea were finalising the £46.3million capture of João Félix.
Of all the wingers in Europe’s top leagues, according to the scouting metrics of fbref.com, statistically the second-most similar to Sterling is Félix. The third? Mykhailo Mudryk.
At Chelsea, it has been another of those weeks. Weeks where you can’t see how the football messaging and corporate decisions align; weeks where things we thought we knew about how to run football clubs have been challenged.
Chelsea released the most beautiful video, celebrating the wide-eyed journey from childhood with the club of Conor Gallagher, which ended with the caption: “You will forever be a blue”. Except the video was to mark selling him — against his will — to Atletico Madrid.
To introduce Félix, who had an indifferent loan spell at Chelsea in 2022-23, the club shot a film of the Portuguese at Cobham, themed around second chances. Meanwhile, elsewhere in the training ground, a 13-strong “bomb squad” of stars cast into footballing Siberia were practising away from Maresca’s group. Deemed surplus to requirements, they have no first-team futures and use the academy facilities and are offered food from the first-team canteen in lunchboxes.
They include Trevoh Chalobah, among Chelsea’s best defenders last season, who has been at the club since he was eight. And Kepa Arrizabalaga, signed as the world’s most expensive goalkeeper, but now one of eight ’keepers on Chelsea’s books, and Romelu Lukaku, recruited for £100million, but now one of three strikers in the bomb squad alone. Winstanley and Stewart are trying to shift them all . . . then sign another striker. Having looked dead a week ago because of the financials, a deal could be back on for Victor Osimhen, with Chelsea edging closer to agreement with Napoli over Lukaku’s sale the other way.
Sterling was criticised for releasing a statement before kick-off against City, where he asked Chelsea for “clarity”. Reputationally, it was a risk, but achieved the objective of getting the club hierarchy to hold talks — the next day — where the parties agreed his Chelsea career was over and to work on finding him a new club. A number of teams in the Premier League are interested and, while his family are settled in London, he hasn’t ruled out a Champions League club in Europe. His main driver is finding somewhere he can get back to his best and into the England team.
The headache for Chelsea is Sterling is owed about £70million, comprising wages and loyalty bonuses, under the terms of his contract, which expires in 2027. He has been given leave from Cobham since Maresca’s bombshell and trains at home, following an intense regime devised by his fitness consultant, the former England performance lead Ben Rosenblatt.
Should he have kept his head down? “Look, Trevoh is being nice — and he’s eating packed lunches,” said a close observer of the club.
Surveying the scene, a fellow club owner wondered about the strategies of Boehly and Eghbali. At Chelsea, players appear to be viewed “as dots on a balance sheet,” he said. He went through the numbers. More than £1.2billion spent on transfers since Boehly and Eghbali took control in 2022, with 39 signings, 36 loans (in and out) and 36 players sold and released. There are 27 players with five seasons or more left on their contracts, and the wages of the bomb squad alone amount to £1.25million per week.
He couldn’t see how it was sustainable. “They’ve spent two years testing the rules that are there to stop them getting into financial trouble. So, might they get into financial trouble?” he asked.
Boehly and Eghbali buy things. It’s what they do. First, Boehly bought bonds, then a life insurance company, Security Benefit Life, and then, borrowing the idea from Warren Buffett, used the dependable monies from insurance to buy more “exciting” assets, stockpiling a trove of more than 100 companies including betting sites, the Golden Globes, Bruce Springsteen’s back catalogue, and the LA Dodgers baseball team. He oversees $70billion (about £53billion) of assets. His UK portrayal as a “dumb American” is asinine — this is a very, very smart guy.
Same with Eghbali. An investment banker specialising in tech, he proved a whizz kid in mergers and acquisitions, becoming one of the youngest billionaires in private equity through his company, Clearlake Capital, which grew rapidly through buying up obscure yet undervalued software, industrial and consumer products companies.
So, since their £4.25billion takeover, they have been acquiring things for Chelsea. Footballers. Staff. Land. A feeder club. They have a playbook to follow in what Boehly did with the Dodgers, who he turned from “America’s worst-run sports team” into an incredible success story via a ferocious programme of hires.
The Dodgers had dropped out of baseball’s top ten in annual payroll and were being outbid on free agents by minor teams before Boehly transformed them into mega-spenders known for signing stars on eye-wateringly long and expensive contracts, such as a £227million 12-year deal for Mookie Betts in 2020 and the unique 20-year £530million deal for Shohei Ohtani — where £514million of wages are deferred for ten years — in 2023.
Going heavy on data and recruitment, the Dodgers also hoovered up some of the best staff from around the MLB, including Andrew Friedman, plucked from the underdog sensations Tampa Bay Rays, and made the highest-paid executive in baseball in a role equivalent to director of football.
What has happened at Chelsea? Long contracts, data-led recruitment and relentless hiring of staff. Who are Europe’s top five clubs for transfer profits? Brighton & Hove Albion, Benfica, Monaco, Ajax and the Red Bull sides. While ignoring Ajax (presumably because Erik ten Hag has already bought everyone) Boehly/Eghbali have hired from Brighton (Winstanley; director of global recruitment, Sam Jewell; head of goalkeeping, Ben Roberts; team doctor, Stephen Lewis), Monaco (Stewart), Benfica (head of performance services, Nick Chadd) and Red Bull (short-lived technical director, Christopher Vivell).
And to which clubs have they paid most in transfer fees? No 1 on the list is Leicester City, but four of the next five are Brighton, Monaco, Benfica and RB Leipzig.
So there is a plan. It’s phone-in show stuff to depict Chelsea as “mental” and spending without a rationale. Whether it’s a good plan is another question. The long contracts are there to offer the club protection (Boehly and Eghbali were “burned” when, within a few weeks of taking over they saw £100million worth of defenders — Antonio Rüdiger and Andreas Christensen — leave as free agents) but do they offer players’ comfort zones rather than the impetus they need to develop?
Another element that might not translate is a recruitment drive heavy on players aged around 20. That’s clever in baseball, a power-based sport where the peak production years are 27-29. But there’s evidence, in football, that it’s slightly younger and that by the age of 20 around 90 per cent of a player’s development has been done.
A better age to sign prospects is around 17 (look at the difference, in career trajectories, for the members of England’s 2017 World Cup-winning Under-17 and Under-20 squads) although in fairness Chelsea are increasingly snapping up teens, and while recruiters at major rivals question the overall quality of the 39 signings, they are wowed by two: Estêvão Willian, 17, who is compared to Lionel Messi and seen as Brazil’s best talent since Neymar, and who will join from Palmeiras next year. And then the £17.3million Ecuador midfield sensation Kendry Páez, also 17 and joining next year.
Chelsea’s take is that transfer fees are only one part of the equation and the average basic wage in the first-team squad has been reduced to about £60,000 per week — which is below the Premier League average. However, the football finance experts Swiss Ramble, using wages plus amortisation (likely to be the Premier League’s measure for new cost control rules) calculated Chelsea’s squad cost for 2022-23 was easily England’s highest, four times as much as Brighton’s and £100million more than supposedly profligate Manchester United.
It’s acknowledged the owners “did what all new owners do and make mistakes” after buying Chelsea — of which one may have been Boehly, acting as sporting director, giving Sterling a £325,000 per week deal without standard reduction clauses covering Chelsea failing to make the Champions League or Europe. The idea there is any interference in Maresca’s football decisions is strongly rebutted. His job is simple — coach the players, pick the team — and in the sweet spot for someone obsessed with tactics and technical details and less interested in communications, club machinations and recruitment.
The explanation for such a heavy volume of player trading is Chelsea were in a unique situation after Roman Abramovich. Sanctions and transfer bans resulted in contracts being run down, squad planning disappear, and unwanted players pile up — some of whom, such as Lukaku and Arrizabalaga, are still difficult to dispose of. Boehly said in a recent Forbes profile: “We just need to let the process develop . . . the good news is people care so much. The bad news is people care so much. That leads to times when they’re frustrated with the team and the owners. I get that, but we just have to continue to stay the course.”
However in February, before the EFL Cup final, the message from high in Chelsea’s recruitment operation was the trading would slow down and summer 2024 would see “evolution not revolution” and buying in “one or two positions”. There was also celebration of Mauricio Pochettino’s role in putting heart and soul in the project via his people skills, his warmth, his ruses to bond the whole club together like a Christmas market, and barbecue in the car park at Cobham for everyone — from players to ordinary staff — and their kids.
It was suggested Chelsea would move away from the bad old days of players perpetually out on loan and groups training away from the first team. Since, we’ve had Pochettino going, the bomb squad, and the signing of 11 players in eight positions. Is there just an addiction to churning and trading? The main title contenders — City, Arsenal and Liverpool — have made four signings between them this summer, while Chelsea keep raiding the transfer fridge.
The club would argue it signed nobody in the January window, that the present window’s focus has been on players for the future, and that at first-team level the changes are relatively few. That their XI starters versus Manchester City were all at the club last season. That Reece James is captain and Levi Colwill looks set for a big role under Maresca, so academy products are still cherished — and that Gallagher, who was offered wages comparable to the club’s highest-earning midfielders albeit on a (by Chelsea standards) piffling two-plus-one-year deal, could have stayed.
Headaches for Winstanley and Stewart include the tightening of Fifa loan regulations. With the exceptions of homegrown and under-21 players, clubs can only make six loans outside national borders, meaning “bomb squaddies” who can’t be sold might have to be farmed to rival English clubs. On Thursday, Maresca secured his first win, against Servette, but it wasn’t convincing, new striker Marc Guiu, had an incredible miss and there were boos at Stamford Bridge.
Chelsea began with £445million on the pitch and £320million on the bench. Servette’s starting XI cost £360,000.