Grading Every Chelsea Transfer Window Under Todd Boehly (2022–2026)

Let’s be real—trying to keep up with Chelsea’s transfer business under Todd Boehly has felt like trying to read a novel while someone flips the pages at double speed. Since the Clearlake Capital takeover in 2022, the club has spent heavily on new signings, cycled through more managers than most clubs see in a decade, and built a young squad that’s somehow both exciting and infuriating. If you’ve found yourself staring at the squad list wondering how we ended up with a bloated senior squad and still no backup left-back, you’re not alone.

But here’s the thing—grading these windows isn’t just about the money spent. It’s about whether the strategy actually worked. Did we get value? Did the players fit? Did the club learn from its mistakes? Let’s walk through each window from 2022 to 2026, troubleshoot the common headaches fans face when trying to make sense of it all, and give each period the honest grade it deserves.

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Summer 2022: The Todd Boehly Chaos Window

Grade: C+

The first window under the new ownership was pure, unfiltered chaos. Boehly had arrived in May, the sporting director structure was basically non-existent, and the manager was Thomas Tuchel—who, by the way, was sacked in September. The club spent significantly, and honestly, it showed.

What actually happened?

Common fan problem: “Why did we sign so many players without a plan?”

Solution: This happens when there’s no sporting director. Boehly was effectively acting as his own director of football, negotiating deals directly with agents. The result? A scattergun approach that targeted big names rather than system fits. If you’re trying to evaluate this window, look at the manager’s system first. Tuchel wanted a back-three with wing-backs, but Cucurella was the only specialist wing-back signed. Fofana and Koulibaly were centre-backs in a system that already had Thiago Silva. The pieces didn’t fit.

When to call a specialist: If you’re a fan trying to understand a chaotic transfer window, check if the club has a clear sporting director or technical director. No director? Expect chaos. For Chelsea, the appointment of Christopher Vivell and later Paul Winstanley was the fix.

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January 2023: The Enzo Gamble

Grade: B-

This window was all about one name: Enzo Fernández. Chelsea triggered his reported release clause on deadline day, making him one of the most expensive signings in British history at the time. The club also brought in Mykhailo Mudryk, Benoît Badiashile, Noni Madueke, and Malo Gusto.

The troubleshooting moment: “Did we overpay for Enzo?”

Short answer: Yes, but with context. World Cup winners are often overpriced in January. Enzo had just won the World Cup with Argentina and was only six months into his Benfica career. The fee was inflated because Chelsea needed a midfielder and Benfica knew it.

Long answer: The real issue wasn’t the fee—it was the timing. Chelsea had already spent heavily in the summer. Adding another significant outlay in January pushed total spending for the season to an enormous sum. That’s not sustainable. The club was betting that Champions League qualification would cover the costs, but they finished well outside the top four. The Financial Fair Play consequences are still being felt.

When to call a specialist: If you’re a fan worried about FFP, look at the club’s amortisation strategy. Chelsea started offering 8-year contracts to spread the cost. That’s a specialist accounting move, not something you can fix by tweaking your fantasy team.

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Summer 2023: The Moisés Caicedo Saga

Grade: B+

This window was defined by one transfer saga that dominated the entire summer: Moisés Caicedo. Chelsea eventually paid a British record fee for him, plus signed Romeo Lavia, Christopher Nkunku, Cole Palmer, and Axel Disasi.

The big headache: “Why did we bid for Caicedo three times?”

Solution: Chelsea’s negotiation strategy was painfully public. They started with lower bids, then increased them, and Brighton kept saying no. The problem? Brighton didn’t want to sell. Chelsea had to pay the premium to force the deal. The lesson for fans: when a selling club doesn’t need to sell, don’t expect bargains.

Cole Palmer: The one that worked

The reported signing of Cole Palmer from Manchester City was the steal of the window. He’s now Chelsea’s best player, with a strong goal contribution record. If you’re grading this window, Palmer alone lifts the grade. The rest of the signings—Caicedo (settling in), Lavia (injured), Nkunku (injured), Disasi (solid but unspectacular)—are mixed.

When to call a specialist: If you’re trying to evaluate whether a player is a good fit, look at their playing time. Caicedo started slowly because he was adapting to a new league and a new system. Palmer hit the ground running because Pep Guardiola had already developed him. Sometimes the answer is “give it time.”

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January 2024: The Quiet Window

Grade: C

Chelsea barely spent in January 2024. The club brought in only one senior signing on loan and focused on selling players to balance the books. The problem? They didn’t solve the squad’s biggest issue: no reliable striker.

Fan frustration: “Why didn’t we sign a striker?”

Solution: This is a classic troubleshooting moment. The club had Nicolas Jackson, who was inconsistent, and Armando Broja, who was recovering from injury. The answer is usually financial. Chelsea had already spent heavily and needed to sell before they could buy. The January window is notoriously difficult for value deals.

When to call a specialist: If you’re wondering why a club doesn’t sign a player in January, check the financial reporting period. Clubs often wait until summer because they have more time to negotiate and sell players. For Chelsea, the summer 2024 window was always going to be the big one.

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Summer 2024: The Reset Window

Grade: A-

This was the window where Chelsea finally looked like they had a plan. The club appointed Enzo Maresca as head coach, sold a significant number of players (including Mason Mount, Kai Havertz, and Mateo Kovacic), and brought in a targeted group of young talents: Liam Delap, João Pedro, Estevão Willian, Alejandro Garnacho, and Pedro Neto.

The strategy shift

The troubleshooting question: “Is this squad too young?”

Common problem: Fans worry that a young squad won’t be competitive. The average age of a Premier League title-winning squad is usually 27-28.

Solution: Look at the mix. Chelsea have veteran leaders in Thiago Silva, Raheem Sterling, and Ben Chilwell. The young players are supplemented by experience. Also, the club won silverware in the 2024/25 season, proving that youth can win trophies.

When to call a specialist: If you’re worried about squad balance, check the minutes distribution. A squad that’s too young can burn out in the second half of the season. Chelsea’s trophy success suggests they have enough depth.

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January 2025: The Consolidation Window

Grade: B

Chelsea made only one significant signing in January 2025: a backup goalkeeper to provide cover for Robert Sánchez. The focus was on extending contracts for key players like Cole Palmer and Enzo Fernández.

The fan problem: “Why aren’t we spending?”

Solution: This is actually a good sign. After years of massive spending, the club was finally balancing the books. They needed to sell before they could buy, and the January window is rarely the time for big moves. The extension of Palmer’s contract was the real win.

When to call a specialist: If you’re a fan frustrated by a quiet window, check the club’s PSR (Profit and Sustainability Rules) position. Chelsea had to sell academy graduates like Mason Mount and Ruben Loftus-Cheek to book pure profit. That’s a specialist accounting requirement, not a lack of ambition.

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Summer 2025: The Macfarland Era Begins

Grade: B

The summer of 2025 was defined by instability. Maresca was sacked mid-season, replaced by an interim coach, and then Calum Macfarland took over permanently later. The transfer window reflected that chaos: Chelsea signed a few squad players but missed out on their top targets.

The troubleshooting moment: “How does a manager change affect transfers?”

Solution: When a manager is sacked mid-season, the summer window becomes reactive rather than proactive. The new manager had to work with the squad he inherited. Chelsea signed a few players for depth but didn’t make a marquee signing.

When to call a specialist: If you’re trying to predict a club’s transfer strategy after a manager change, look at the new manager’s preferred system. Macfarland is reported to favour a 4-3-3, which means Chelsea need a proper defensive midfielder and a left-back. The squad is still unbalanced.

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The Final Grade: Overall Boehly Era (2022–2026)

Grade: B-

The troubleshooting summary

If you’re a Chelsea fan trying to make sense of the Boehly era, here’s the cheat sheet:

1. Chaos windows (Summer 2022, January 2023) happen when there’s no sporting director. The fix is to hire one.
2. Overpaying happens when you’re desperate. The fix is to plan ahead and identify targets early.
3. Squad imbalance happens when you sign players for different systems. The fix is to commit to a manager’s vision.
4. Financial constraints happen when you spend too much too quickly. The fix is to sell academy graduates and use amortisation.

The Boehly era has been a rollercoaster, but there’s finally a plan. The squad is young, talented, and has already won silverware. Whether that translates into Premier League titles depends on Macfarland’s ability to mould this group into a cohesive unit.

For more on how Boehly’s spending compares to the Abramovich era, check out our detailed comparison. And if you want to understand the long-term implications of this transfer strategy, read our analysis on Boehly’s transfer legacy.