Chelsea’s alarming dip in form has put sporting directors Paul Winstanley and Laurence Stewart under intense scrutiny, with fans and pundits alike blaming their decision-making for the club’s current struggles. The Blues have won just three of their last 11 games, despite spending over £1 billion on transfers since the duo’s appointment in January 2023.

Winstanley and Stewart, who arrived from Brighton and Monaco to replace Christopher Vivell, have overseen a recruitment strategy focused on young talent under the age of 25. However, results on the pitch have failed to justify the investment, and Chelsea’s squad appears no closer to competing for major trophies.

The winter transfer window was another disappointment, as Chelsea spent most of their time pursuing wingers like Alejandro Garnacho, Jamie Bynoe-Gittens, and Mathys Tel—only for none of them to arrive. Meanwhile, a long-standing striker problem remains unsolved.

The club showed interest in Aston Villa’s Jhon Duran, but the Colombian ended up moving to Saudi Arabia in a £64m deal. Chelsea then decided to pull out of the race, citing concerns over his suitability. Now, with both Nicolas Jackson and Marc Guiu sidelined due to injuries, the lack of a proper No.9 is being felt more than ever.

Despite Champions League qualification being a realistic target this season, Chelsea’s failure to sign a striker last summer and again in January is seen as a major oversight. The club was also linked with Napoli’s Victor Osimhen, but negotiations fell through due to concerns over his wage demands—an issue that raises questions about whether those leading negotiations planned adequately before engaging in talks.

Adding to the frustrations, Chelsea’s transfer approach has appeared more profit-driven than squad-building. Fan-favorite Conor Gallagher was sold to Atletico Madrid last summer, despite being one of Chelsea’s best performers the previous season. Meanwhile, Stewart and Winstanley’s managerial appointment of Enzo Maresca is also under scrutiny, with many believing they opted for a coach who would comply with ownership rather than a proven title-winner like Hansi Flick, who is now thriving at Barcelona.

With billions spent and little to show for it, Chelsea’s squad appears weaker than the one Todd Boehly and Clearlake inherited from Roman Abramovich. As the season progresses, the pressure on Winstanley and Stewart will only intensify, with fans growing increasingly frustrated by the club’s direction.