First Player Leaves Chelsea Days After Liam Rosenior Appointment
Published 13:59 10 Jan 2026 GMT
It is the first transfer deal of the Rosenior era.
The first departure of the Liam Rosenior era has been confirmed, with Chelsea including a sell-on clause as part of the deal.
Rosenior, who made a name for himself at Strasbourg after leading the Ligue 1 side to European football for the first time in two decades, has taken charge at Stamford Bridge following the departure of Enzo Maresca.
The 41-year-old was only appointed by Chelsea this week, but the former Fulham, Reading and Hull City defender has already given the green light to a January departure.
It was confirmed on Friday that Chelsea's former under-18s and under-21 captain Leo Castledine has left the Blues to join Championship high-flyers Middlesbrough on a four-and-a-half-year deal.
Castledine attracted interest from a number of clubs following a recent loan spell at Huddersfield Town, where he scored 10 goals in 23 appearances for the League One outfit this season.
Liam Rosenior was appointed by Chelsea this week. Image credit: Getty
Liam Rosenior was appointed by Chelsea this week. Image credit: Getty
Middlesbrough will initially pay just under £1 million for Castledine, according to Teesside Live, with Chelsea including a future sell-on fee for the highly-rated forward.
Speaking on his arrival at the Riverside, Castledine said: "I’m absolutely over the moon to join what is a massive, massive club. It’s a really big step for me in my career and I’m very excited to be here.
"There’s always been trust in young players at this club if they can perform, and I want to perform at my highest level."
He added: "I’m fit, healthy and I’ve been playing well, so I feel ready to go. I want to help the team as much as I can from the first day."
Boro head coach Kim Hellberg was full of praise for Castledine ahead of his arrival.
"He’s a good player. He’s done a brilliant job at Huddersfield - doing a lot of good stuff," said Hellberg. "He is capable of scoring a lot of goals. So he is a good player.”
Castledine was labelled a 'wonderkid' during his time at Chelsea. Image credit: Getty
Castledine was labelled a 'wonderkid' during his time at Chelsea. Image credit: Getty
Rosenior, meanwhile, arrives at Chelsea having managed over 150 matches in his short four-year career as a manager. He has signed a six-and-a-half-year contract at Stamford Bridge.
"I am extremely humbled and honoured to be appointed head coach of Chelsea Football Club," he said this week. "This is a club with a unique spirit and a proud history of winning trophies."
Featured Image Credit: Getty Images
Topics: Chelsea, Chelsea Transfer News & Rumours, Premier League, EFL Championship