Michael Emenalo has ended his 10-year association with Chelsea following his sudden departure as the club's technical director as questions continue to mount over Antonio Conte's managerial reign at the club.
The news surrounding the 52-year-old, who could be set to join Monaco, will come as a major blow to owner Roman Abramovich.
The Blues have won the Premier League title three times, the FA Cup, the League Cup, the Europa League and the Champions League while Emenalo has been at the club.
The latest Premier League triumph came under current boss Conte in his first season in English football. However, the Italian's second campaign has proved less successful so far.
Emenalo watched Chelsea beat title rivals Manchester United 1-0 at Stamford Bridge on Sunday afternoon - sitting behind the Blues' dugout.
The win in west London was without David Luiz - who was omitted from the squad after falling out with Conte.
Conte's bust-up with Luiz is the latest falling-out between the manager and a star player at Chelsea. He has previously fallen out with Diego Costa and Nemanja Matic, who both left the club.
The manager was defiant at full-time, saying the Brazilian could face a lengthy spell out unless he learns to get on with his team-mates.
Speaking to Sky Sports, the manager said: 'Christensen is 22 years old, he showed great personality, for sure he is the present and the future for Chelsea, the same for Ampadu.
'David Luiz has to work with the others if he deserves to play, otherwise he will stay on the bench or in the stands.'
Conte was the 10th manager appointed during Emenalo's time in west London and the former has been highly critical of Chelsea's transfer activity this summer.
The former Juventus boss has bemoaned the lack of options available to him following a summer window that only brought in Alvaro Morata, Antonio Rudiger, Tiemoue Bakayoko, Danny Drinkwater, Davide Zappacosta and Willy Cabellero.
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