Tottenham Hotspur have made initial enquiries into the availability of Chelsea sporting director Paul Winstanley as they step up their search for a new sporting director, in a move that could have significant implications for their managerial hunt this summer.
Spurs are looking to fill the sporting director role left vacant following Fabio Paratici’s departure, with Johan Lange currently in place. Football.london understands the club has made contact to check on Winstanley’s availability, though sources close to Chelsea insist he will not be leaving Stamford Bridge, where he holds a contract running until 2031. Winstanley joined Chelsea from Brighton in 2022.
Tottenham have also been linked with Dougie Freedman, the former Crystal Palace sporting director who departed Selhurst Park around a year ago and is currently working with Saudi second-tier club Al-Diriyah FC.
The significance of the Winstanley interest extends beyond the sporting director search itself. The Chelsea man previously worked alongside Mauricio Pochettino at Stamford Bridge, having played a key role in the Argentine’s appointment as Chelsea manager in the summer of 2023. The pair worked together for less than a year before Pochettino was dismissed in June 2024.
Pochettino is currently managing the United States national team, with his contract running until after this summer’s World Cup. Speaking recently, he left the door open to what might follow, saying he was open to everything once the tournament concludes.
Tottenham will require a permanent manager this summer after Igor Tudor took over on an interim basis, having lost both of his Premier League matches in charge so far following Thomas Frank’s departure. Pochettino, who managed Spurs between 2014 and 2019, has been heavily linked with a return to the club.
Should Tottenham successfully appoint Winstanley, his existing relationship with Pochettino could smooth the path toward a potential reunion at Spurs.
