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Chelsea sporting directors safe in end-of-season review and will lead summer spending again

Laurence Stewart and Paul Winstanley of Chelsea during the FA Youth Cup Quarter Final match between Millwall U18 and Chelsea U18 at The Den on February 21, 2024 in London, England

Chelsea’s sporting directors, Paul Winstanley and Laurence Stewart, are not facing doubts over their positions as the club prepare for next week’s end-of-season review.

While the future of head coach Mauricio Pochettino will ultimately be decided when the season is fully assessed in the days after the final game against Bournemouth, Winstanley and Stewart are not thought to be in a similar situation.

Indeed, Winstanley and Stewart, who attended Chelsea’s victory over Nottingham Forest with co-controlling owner Behdad Eghbali, retain the enthusiastic backing of prominent figures on the club’s board.

The pair are expected to continue to lead Chelsea’s transfer business this summer, with the club looking to sign a forward, left-back and central defender. The goalkeeping position may also be looked at.

The remit of Winstanley and Stewart extends much further than recruitment, with sources indicating that a lot of their work goes unnoticed outside Stamford Bridge and Chelsea’s Cobham training ground.

Winstanley and Stewart have faced criticism at times this season, following an overhaul of the squad last summer that saw the average age of the playing staff drastically cut.

That has been blamed by some people for Chelsea’s inconsistency, while Pochettino has suggested that some of the responsibility for the difficulties the club have faced should be shared.

But bosses of Winstanley and Stewart are delighted with their overall work, and believe they will be further helped by the addition of director of global recruitment Sam Jewell, who started work last week and reports to them.

Cole Palmer has been the most obvious success story for Winstanley and Stewart, but Chelsea have also been delighted with signings such as Nicolas Jackson, who has now scored 14 Premier League goals, and Malo Gusto.

Chelsea's Cole Palmer
The signing of Cole Palmer has proved a masterstroke - Reuters/Molly Darlington

Record signing Moises Caicedo has performed impressively over recent months after taking some time to show his best form, while Noni Madueke and Mykhailo Mudryk have managed to hold down regular starting spots during Chelsea’s upturn in form and results.

Mudryk scored against Forest, while Madueke netted against West Ham United and Aston Villa. It is hoped that Romeo Lavia and Christopher Nkunku, whose first seasons were ruined by injury, can make big contributions next term.

Goalkeeper Djordje Petrovic, signed in a £14 million deal, has proved himself to be a value-for-money addition, although £25 million signing Robert Sanchez lost his place and Chelsea could look again at that department.

While there is an acceptance that mistakes were made during the first transfer window overseen by the new ownership, in summer 2022, there is now a feeling that the work of Winstanley and Stewart since then is starting to bear some fruit.

Winstanley started work in November 2022, with Stewart starting his job as co-sporting director in February 2023.

Chelsea remain excited by the potential of midfielder Andre Santos, who has spent the second half of the season on loan at Strasbourg, who are also owned by Clearlake Capital and Todd Boehly.

Despite the fact Kai Havertz could win the Premier League title at the end of his first season at Arsenal, Chelsea believe the work of Winstanley and Stewart on selling players has proved to be successful.

It remains to be seen whether or not Chelsea now relax their recent policy of signing players aged under 25, or whether Pochettino makes a case for bringing in some more experience when he meets with Winstanley, Stewart and the club’s ownership next week.

Since Boxing Day last year, only three teams - Manchester City, Arsenal and Liverpool - have won more points than Chelsea which suggests the squad, under Pochettino, is on an upward trajectory.

The end-of-season review will focus on performance over the entirety of the campaign, which could lead to some awkward conversations over the first half of the season when Chelsea suffered a number of difficulties.

Pochettino has made it clear that his future also lies in his own hands, as well as those in charge at Chelsea. Other than the club wanting to assess his performance, the Argentine, who has admirers outside Stamford Bridge, will want to be confident in the plans of Winstanley, Stewart and the owners.

Chelsea have denied a claim that the club are working on a deal to effectively sell their Cobham training base back to themselves to help satisfy profit and sustainability rules.

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