New Chelsea head coach Liam Rosenior has swiftly begun shaping his squad, approving the permanent departure of academy product Leo Castledine to Middlesbrough. The 20-year-old midfielder is set to undergo a medical at the Riverside Stadium on Friday, marking the first transfer of the Rosenior era.
Castledine's Chelsea Exit Confirmed
Leo Castledine will join Middlesbrough in a deal worth close to £2 million, with Chelsea understood to have secured a sell-on clause for the future. The young attacker has spent this season on loan at Huddersfield Town, where he impressed with a return of 12 goals and five assists.
Castledine's journey with Chelsea has been long but yielded limited first-team action. He originally joined the Blues' academy at five, briefly moved to AFC Wimbledon, before being re-signed in 2020. His sole senior appearance came in a 6-1 Carabao Cup win over Middlesbrough in January 2024, the same club that will now become his permanent home.
Rosenior's First Major Decisions
While overseeing his first training session on Thursday ahead of Saturday's FA Cup third-round tie at Charlton Athletic, Rosenior has been active behind the scenes. Beyond sanctioning Castledine's move, his inaugural major staffing decision has been to invite caretaker manager Calum McFarlane to join his backroom team as an assistant.
McFarlane, 37, steadied the squad after Enzo Maresca's dismissal on New Year's Day, overseeing a credible draw at Manchester City before Wednesday's defeat to Fulham. Rosenior, who watched the Fulham loss from the stands at Craven Cottage, was reportedly struck by McFarlane's handling of a turbulent period and personally offered him the role.
Looking Ahead to the FA Cup
All focus now turns to Rosenior's touchline debut this weekend. Chelsea travel to face Championship side Charlton Athletic, offering the new boss an immediate chance to imprint his philosophy and secure progress in the famous domestic cup competition. The integration of McFarlane and the resolution of Castledine's future represent Rosenior's first concrete steps in what promises to be a busy January at Stamford Bridge.
