Chelsea's recruitment is focused long-term – is it too early to judge Winstanley and Stewart?

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Chelsea's recruitment is focused long-term – is it too early to judge Winstanley and Stewart?

Chelsea’s impressive dismantling of Aston Villa in their FA Cup replay was a timely boon for head coach Mauricio Pochettino, but the performance may have been an even greater source of relief for the two men above him.

Laurence Stewart and Paul Winstanley have maintained low public profiles since being announced as the co-sporting directors at the end of January 2023. Chelsea did not make them available to talk to the media during pre-season, despite both men travelling around the United States with the squad, and the bulk of their pronouncements to date were made in soft-focus in-house interviews in September.

Yet their names are the ones increasingly raised by disgruntled supporters when dark days such as the 4-2 home defeat against Wolverhampton Wanderers raise bigger questions about the promise of the lavish youth investment project at Stamford Bridge. At such times, when even some of the flagship signings of the Todd Boehly-Clearlake Capital ownership do not look good enough, who better to hold to account than the two men tasked with leading Chelsea’s recruitment?


Stewart talking to Frank Lampard at Stamford Bridge (Sebastian Frej/MB Media/Getty Images)

There are no indications that Winstanley or Stewart are in danger of losing their jobs anytime soon; on the contrary, further additions to the sporting structure are planned in the coming weeks, with all new hires reporting to them. That may be unsatisfying for some of the angrier Chelsea fans, but it should not come as a surprise — particularly when the responsibility for the transfer spending since the departure of Roman Abramovich is assigned properly.

Winstanley was brought from Brighton & Hove Albion to Chelsea, initially with the grand title of ‘director of global talent and transfers’, in November 2022. Stewart agreed to join from Monaco the previous month but did not officially begin work until February 2023, when the restructuring that led to them being named co-sporting directors took place.

As a pairing, they have been chiefly responsible for two transfer windows: summer 2023, when a little more than £400million ($505m) committed to new signings was offset by around £215m in player sales, and January 2024, when Chelsea’s only incomings and outgoings were loan deals. Winstanley played a significant role in the January 2023 recruitment drive but the process was different, with Clearlake co-founder Behdad Eghbali actively engaged in the negotiations that brought Mykhailo Mudryk and Enzo Fernandez to Stamford Bridge.

Put simply, these are still relatively early days for Chelsea’s revamped sporting structure, and many of the clearest transfer missteps of the Boehly-Clearlake era pre-date it: Wesley Fofana, Marc Cucurella, Kalidou Koulibaly and Pierre-Emerick Aubameyang were all signings made by interim sporting director Boehly, partly at the request of head coach Thomas Tuchel. The subsequent sacking of the German and appointment of Graham Potter can be added to the list of big football decisions made before Stewart and Winstanley were in post.

None of the above should grant them immunity from scrutiny for what has happened on and off the pitch since. Pochettino, their hire as head coach, has struggled to improve on the Premier League form that cost Potter his job. A year into their tenure, Chelsea’s crippling injury problems are only just beginning to ease and the list of unequivocal recruitment wins might extend no further than Cole Palmer and perhaps Djordje Petrovic, who has looked a reliable alternative to Robert Sanchez in recent weeks.

In that regard, the Villa win was not quite a validation, but it was a timely demonstration of the quality identified in the likes of Malo Gusto, Benoit Badiashile, Axel Disasi, Noni Madueke, Palmer and Nicolas Jackson. It was a reminder that individual talent is far from the sole determinant of success or failure at this level.

Pochettino picked his most cohesive starting XI in months at Villa Park and suddenly the theory of a serious Chelsea team became much clearer: two mobile centre-backs capable of defending high up as well as deep gave flexibility, flanked by dynamic natural full-backs. Stationed much closer together, the £200million Fernandez-Moises Caicedo midfield axis offered control with less risk of being overrun. At the tip of the spear, a devilish pressing tandem of Palmer supported by Conor Gallagher tormented the home side. Out wide, two wingers prepared to defend as well as attack provided balance.

Few footballers can be the best versions of themselves without a team context that amplifies their strengths and minimises their weaknesses. Badiashile and Disasi look most confident when rekindling their old Monaco partnership. Caicedo appears more comfortable in a tighter tactical structure more akin to his Brighton experience. Fernandez is much more impactful on the ball than ahead of it. Jackson has numerous good No 9 attributes but part of his future value may actually lie in his original position on the left wing.

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Winstanley has a focus on the long-term (Nick Potts/PA Images via Getty Images)

It would be foolish in many cases to dismiss the talent that Chelsea have assembled purely because the team’s Premier League results have been underwhelming. More pertinent is whether the bigger Boehly-Clearlake project — turning the first-team squad into an investment portfolio of promising young footballers on ultra-long contracts — is fundamentally flawed.

The belief underpinning the transfer strategy of Chelsea’s owners is that youth in football is underrated. This is why they have repeatedly paid premiums for potential rather than proven quality, a break from conventional wisdom. It has set them on a path that no club has walked before, one that demands they develop young talent in their first team while competing consistently at the highest level.

Can it be done? Some at Chelsea might point to the Villa win, achieved by a starting XI with an average age of 22.8, as cause for optimism. Many others outside Stamford Bridge will be more inclined to cite their prolonged slide into Premier League mediocrity, an increasingly toxic home atmosphere and many young players seemingly struggling under the weight of lofty expectations, as a compelling body of evidence against the Boehly-Clearlake vision.

Stewart and Winstanley will be evaluated in the longer term on whether they can build a club capable of walking that path, and the impact of their signings will be only one of several factors considered. Chelsea are still looking to add specific expertise to their medical department, chiefly to address a dramatic rise in hamstring injuries this season. The travails of several young players in the first half of the campaign have highlighted room for improvement in the loan system. There is also the performance of Pochettino, who has only one more guaranteed year on his contract this summer, and whoever might succeed him.

The scale of the challenge is daunting, and particularly so for two men who have not led the sporting operations at any of their previous clubs. The ownership’s faith in them to take it on has not been shaken by supporter criticism, but more days like the one Chelsea enjoyed at Villa Park will be welcome as they strive for longevity as well as success.

(Top photo: Darren Walsh/Chelsea FC via Getty Images)