How Raheem Sterling actually transformed Chelsea’s entire recruitment strategy
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(Credit: Imago)
Ben Palmer
Thu 25 September 2025 16:10, UK
Chelsea’s signing of Raheem Sterling is one of many mistakes the club have made in the transfer market.
The 30-year-old joined the Blues in July 2022 for a fee of £47.5million as one of Todd Boehly and Clearlake Capital’s marquee signings, following their takeover of the club.
The winger played out two unremarkable seasons at Stamford Bridge before Enzo Maresca quickly discarded the England international, with Sterling joining Arsenal on loan for the 2024-25 campaign.
Since returning this summer, Sterling has been exiled from the Chelsea first team, and the Blues are struggling to find a solution for one of world football’s best-paid players.
And consequently, the West London club have adapted their approach to the contracts that are now handed out, because of the ex-Man City man.
Credit: Imago
As reported in The Athletic: “Sterling is one of the reasons the Todd Boehly-Clearlake consortium soon changed to offering incentivised rather than guaranteed contracts.”
The winger is making around £300,000 a week, which likely puts him in the top 10 of the Premier League’s highest earners.
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Chelsea have become renowned for their long-term contracts that they offer to new signings.
Initially, this strategy was employed as a clever way of sidestepping the rules on transfer fee amortisation, allowing the Blues to spread the cost of a new signing over seven or eight years.
Credit: Imago
UEFA closed that loophole, limiting the amortisation length to five years, but Chelsea continues to sign players like Jamie Gittens on long-term deals.
Offering a player a longer deal that stretches out guarantees and gives players a sense of comfort is a smart move that works for both parties.
This can backfire if a player is no longer included in the manager’s plans, but Chelsea has proven themselves a savvy selling club this summer, Sterling aside.
Another aspect of Chelsea’s recruitment that cannot be overlooked is the profile of players that they have targeted since Boehly’s first summer in charge.
In the 2022-23 window, Sterling arrived as a 27-year-old who had scored 17 goals in 47 games the season prior for City, a sharp downturn in the form he displayed between 2017 and 2020.
A 31-year-old Kalidou Koulibaly also joined from Napoli, whilst Pierre-Emerick Aubameyang returned to England after a season with Barcelona.
The striker was 33 at the time.
All three players, whilst they had their moments, proved to be more of a headache than they were worth, with both Koulibaly and Aubameyang leaving after one season at the club.
Instead of targeting players in their prime, the Blues have gone after the leading young talent that world football has to offer.
Credit: Imago
The only player older than 25 that has been signed in the ensuing windows was Tosin Adarabioyo, a 26-year-old free agent from Fulham in July 2024.
Some signings have worked out better than others.
Angelo Gabriel, Lesley Ugochukwu, and Deivid Washington all signed in the 2023-24 summer and have since departed without making an impact on the pitch.
But the key note of difference is that, thanks to their cheaper contracts and potential to improve, other clubs were willing to take a chance on them, and that change in transfer approach is the reason why Chelsea can continue to buy and sell so freely, and perhaps why they have found it so difficult to shift Sterling.