Chelsea FC’s squad size has ballooned to staggering proportions since the Todd Boehly-led consortium took over in 2022. With more than three dozen signings and a revolving door of managers, Stamford Bridge has become a hub of footballing activity.
The club’s January transfer window promises more drama as Enzo Maresca seeks to trim his overloaded roster. Several players, including some experienced professionals, find themselves on the fringes, desperate for an exit to revive their careers.

Among those players are Ben Chilwell, Kiernan Dewsbury-Hall, and Tosin Adarabioyo. Despite their potential and past performances, they’ve struggled to find regular game time and could benefit from a fresh start.
Once a cornerstone of Chelsea’s defence, Ben Chilwell has endured a rapid fall from grace. The 28-year-old left-back, a Champions League winner in 2021, has been relegated to the sidelines under Maresca. He has managed just one appearance this season, excluded from the Premier League and Conference League squads altogether.
Clubs across England are reportedly circling, eager to capitalise on Chilwell’s situation. His defensive solidity, overlapping runs, and knack for delivering in clutch moments make him an attractive option. For Chilwell, leaving Chelsea in January could reignite his career and offer the consistent minutes he craves.
After a £30 million move from Leicester City in July, Kiernan Dewsbury-Hall’s dream of breaking into Chelsea’s midfield has turned into a nightmare. The 26-year-old, who starred under Maresca at Leicester, has been confined to sporadic appearances in the Conference League and Carabao Cup, with just five substitute appearances in the Premier League.
Despite his limited minutes, Dewsbury-Hall has showcased glimpses of his quality, including two goals in the Conference League. However, his inability to secure a regular starting role has stalled his progress. For the midfielder, a January departure – whether a loan or a permanent move – could provide a lifeline to recapture his form and make his case for England selection.
A Leicester midfielder moving to Chelsea for 30-odd million pounds, and then slowly wasting his career in the reserves – Dewsbury-Hall will do everything in his power not to emulate Danny Drinkwater’s career.
Tosin Adarabioyo’s arrival at Chelsea on a free transfer from Fulham was heralded as a shrewd move. Yet, the 27-year-old centre-back has found himself buried in a congested defensive line, managing just 11 appearances across all competitions.
Despite his strong performances in cup matches, Adarabioyo remains behind Wesley Fofana, Levi Colwill, and Axel Disasi in the pecking order. With West Ham reportedly interested, the January window presents an opportunity for the former Manchester City youth player to escape his Stamford Bridge struggles.
Whether or not the move materialises is one to be seen, with the English defender gaining more prominence in the first team due to long-term injuries to Chelsea’s starting defenders.