Tottenham Hotspur are on the lookout for a sporting director as work continues behind the scenes to put a solid structure in place.
After Fabio Paratici left to join Fiorentina last month, Johan Lange is the only one who has served in that role as they scour the market to replace the experienced Italian.
The new sporting director is expected to play a big role in their managerial search, which will take centre stage after the season concludes.
According to a report from Telegraph Sport, Chelsea’s Paul Winstanley is one of the candidates admired by the club.
If he were to take the role, Mauricio Pochettino’s hopes of an emotional return to Tottenham could be as good as over.
Winstanley and Poch have a history
Winstanley has been at Chelsea since 2022 and has overseen the signing of Cole Palmer, Enzo Fernandes, Joao Pedro and Moises Caicedo, among others.
He has also played a pivotal role in appointing a handful of managers at the club, including Pochettino, Enzo Maresca and Liam Rosenior, most recently.
Pochettino has been linked with a return to Tottenham after his 2026 FIFA World Cup commitments with the USA National Team.
His most recent stint in the Premier League was with Chelsea, where he oversaw the reigns at Stamford Bridge during the 2023-24 season.
While Winstanley played a big role in Pochettino’s arrival, a report from the Telegraph after his sacking paints an interesting picture.
A key reason behind his Chelsea exit was due to philosophical differences. While the Argentine wanted more control, the Blues’ top brass preferred a manager who could work well within their structure, which could diminish the head coach’s influence within the club.
It’s not to say the pair have bad blood between them, but considering their previous spell together ended rather unceremoniously, it remains unlikely that they will reunite at N17.
Who else do Tottenham want?
With Winstanley held in high regard at Chelsea and tied down at the club until 2031, the North London club face an uphill battle to prise him away from Stamford Bridge.
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Former Crystal Palace sporting director Dougie Freedman is also on Tottenham’s radar, having earned plaudits for his work at Selhurst Park with the notable captures of Eberechi Eze, Adam Wharton, Michael Olise and Marc Guehi, among others.
However, he only joined Al-Diriyah last year, so it’s unclear whether he would be willing to jump into another new role so quickly.
