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Tottenham Chelsea approach could give Mauricio Pochettino return green light
Reach Daily Express | March 3, 2026 5:39 AM CST

Tottenham have approached Chelsea regarding a possible move for sporting director Paul Winstanley, as they seek a replacement for Fabio Paratici to work with Johan Lange.

Spurs are intensifying their hunt for a new sporting director, following Paratici's exit in January, with preliminary enquiries made regarding prospective candidates. Among them was Winstanley, who has been at Chelsea since arriving from Brighton in 2022.

football.london reports that Tottenham have made early checks on the Chelsea man's availability, though sources close to the Blues maintain that he will not be departing. Winstanley remains under contract at Stamford Bridge until 2031.

Spurs have additionally shown an interest in former Crystal Palace sporting director Dougie Freedman. The 51-year-old departed Selhurst Park nearly a year ago, and currently holds the sporting director role with Saudi second-tier outfit Al-Diriyah FC.

Whichever new sporting director arrives at Tottenham, they are expected to wield considerable influence over the managerial appointment facing the club this summer. Igor Tudor took charge on an interim basis last month, though he has suffered defeat in both his Premier League fixtures to date.

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Spurs will be searching for a permanent replacement for Thomas Frank come the summer. They have been strongly connected with a potential return for former boss Mauricio Pochettino.

The Argentine is currently at the helm of the USA national team, but could potentially be up for grabs following this summer's World Cup. If Spurs decide to pursue Winstanley more aggressively, it could bode well for their potential chase of Pochettino, given their previous collaboration at Stamford Bridge.

Pochettino was brought on board by Chelsea in the summer of 2023, with Winstanley likely playing a significant role in his recruitment. The pair worked together for just shy of a year before Pochettino was dismissed in June 2024.

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Just last week, Pochettino hinted at the possibility of a summer return to Spurs, over six years after his departure.

"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.

"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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