Tottenham made initial checks on the Chelsea man as they continue their sporting director search
18:42, 02 Mar 2026
Todd Boehly co-owner of Chelsea FC with Sporting Director Paul Winstanley during the Premier League match between Chelsea and Crystal Palace at Stamford Bridge.
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Tottenham have made initial checks on the availability of Chelsea sporting director Paul Winstanley. (Image: Robin Jones/Getty Images)
Tottenham have made contact over a potential move for Chelsea sporting director Paul Winstanley, as they search for a replacement for Fabio Paratici to work alongside Johan Lange.
Spurs are stepping up their search for a new sporting director, with checks made on potential candidates. One of those was Winstanley, who has been with Chelsea since joining from Brighton in 2022.
football.london understands that Tottenham have made initial checks on the Chelsea man’s availability, but sources close to Chelsea insist that he is not going anywhere. Winstanley has a contract at Stamford Bridge until 2031.
Spurs have also been linked with an interest in former Crystal Palace sporting director Dougie Freedman. The 51-year-old left Selhurst Park just under a year ago, and is currently the sporting director with Saudi second-tier side Al-Diriyah FC.
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Whoever the new sporting director may be at Tottenham, he is likely to have a big say on the managerial decision facing the club in the summer. Igor Tudor arrived on an interim basis last month, but has lost his two Premier League games in charge so far.
Spurs will be on the lookout for a permanent successor to Thomas Frank in the summer. They have been heavily linked with a move for former manager Mauricio Pochettino.
The Argentine is currently manager of the USA national team, but could possibly be available after this summer's World Cup.
Mauricio Pochettino prior to a game against Costa Rica.
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Mauricio Pochettino has been linked with a return to Tottenham (Image: Julio Aguilar/Getty Images)
If Tottenham do push further for Winstanley, then it could be a good sign in a potential pursuit of Pochettino, with the two working together previously at Stamford Bridge.
Pochettino was appointed by Chelsea in the summer of 2023, with Winstanley likely to have played a big part in his arrival. The two worked together for just under a year before Pochettino was sacked in June 2024.
Speaking last week, Pochettino has hinted that he could be open to a summer return to Spurs, six-and-a-half years after his exit.
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“I'm always linked (to clubs). To Tottenham, just like at one time I was linked to Espanyol, or to other clubs,” he said
"In the end, especially because of my past at those clubs, when things aren't going well, people tend to fall back on emotion and say, 'Well, with Mauricio we played good football,' or whatever it may be.
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"But no, we're focused on the World Cup, on the United States. My contract runs until after the World Cup, so after that we'll see what might happen. Open to everything, right?"
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