Raheem Sterling is reportedly set to call it quits at Chelsea in the winter transfer window.
Chelsea and Raheem Sterling are edging closer to ending what has become one of the most underwhelming chapters of the Todd Boehly era. Having spent the 2023/24 season on loan at Arsenal and earning a staggering £300,000 a week without featuring for Chelsea since May 2024, the 29-year-old winger is now expected to depart Stamford Bridge before the January transfer window closes on February 2.
According to a report by Sky Sports, talks between Chelsea and Sterling’s representatives have reportedly advanced in recent days. While there is still no confirmed destination, both parties are motivated to find a solution that avoids further standoff.
Chelsea are open to a permanent exit, while Sterling has made it clear he does not want another loan spell. This narrows the options, especially in a tight market, but could accelerate a mutual contract termination or a low-fee permanent transfer.
Signed in July 2022 for £50 million from Manchester City, Sterling was one of the marquee acquisitions of the early Boehly-Clearlake era. He had earlier made his name at Liverpool, before joining Manchester City in 2015. The hope was that his experience, directness, and Premier League pedigree would help stabilize a young and evolving Chelsea side.
Instead, the Englishman”s time at the club has been marked by inconsistency, injuries, and managerial upheaval, all of which prevented Sterling from ever finding sustained form or rhythm. Despite a few flashes of brilliance in his debut season, Sterling never became the attacking leader Chelsea envisioned.
His loan spell at Arsenal last season offered limited redemption, with 28 appearances but no permanent move materializing. Now, with 18 months left on a contract that could cost Chelsea around £25 million if allowed to run its course, the club is keen to cut its losses. The timing is crucial.
With Chelsea already under scrutiny for bloated wages and poor return on investment under the new regime, Sterling’s departure could ease financial pressure and open the door for reinforcements who fit the vision of Liam Rosenior. Raheem Sterling’s impending exit is symbolic of Chelsea’s misfires in the transfer market since the ownership change.
While the move made sense on paper, it lacked long-term planning and footballing foresight. Sterling was a short-term fix in a club crying out for a rebuild. Now, with younger talent emerging and a manager focused on tactical identity, there is little room for sentiment.
Chelsea must be bold and decisive, not just in letting go of expensive underperformers like Sterling, but in finally building a squad with cohesion and clarity. The Boehly era must learn from this mistake or risk repeating it. Meanwhile, it will be interesting to see where the English attacker lands, having been linked with Napoli and Premier League clubs in recent weeks.
