When you spend as much as Chelsea have on players over the past two decades – and turn over your squad at a rate of knots – there’s always likely to be an expensive flop or two along the way.
That likelihood has intensified in the Todd Boehly era, with the Blues owner only too happy to take a chance on young talent in the transfer market… with a mixed bag of results as far as return on investment is concerned.
Quite what the ROI on Joao Felix will be remains to be seen, but the 25-year-old – who only joined Chelsea in August 2024 – looks set for the exit door after less than a season on the books.
The Portuguese forward joined AC Milan on loan in January 2025, and has already expressed his delight at the move – suggesting he wouldn’t mind making it a permanent transaction come the summer.
✨ GIMENEZ x JOAO FELIX 🥄#MilanRoma #CoppaItaliaFrecciarossa pic.twitter.com/htCfmYOHx9
— Lega Serie A (@SerieA) February 6, 2025
It’s unlikely, however, that Milan will be able to match the £52 million that Chelsea paid for Felix from Atletico Madrid, and with the player wanting away – citing a lack of Premier League game time – it’s probable that the Blues will have to take a considerable financial hit on the player for any permanent deal to be made.
It’s quite plausible that Chelsea will lose £20-30 million on Felix in less than a year if they want to get rid of him, which is an extraordinarily poor return on investment for a player that featured just three times in the Blues’ Premier League campaign of 2024/25.
And it would see Felix enter the Chelsea hall of shame with regards to the club’s most expensive transfer flops.
Romelu Lukaku
Headlining the rogue’s gallery is Romelu Lukaku, who – at the time of writing – is Chelsea’s third most expensive signing in history. The return on that investment was… disappointing, to say the least.
He returned to Chelsea for a club record fee of £97.5 million in August 2021, having established himself as a world class goal-getter with former employer Inter Milan.
But Lukaku’s second stint at Stamford Bridge was calamitous. He started just 16 Premier League games during the 2021/22 campaign, plus four more in the Champions League, and his seasonal goal return of ten came at a healthy cost of £9.7 million per goal.
To make matters worse, the Belgian had an almighty falling out with then head coach Thomas Tuchel, so he was shipped out on loan to Inter and Roma respectively from 2022 to 2024.
Chelsea finally managed to get rid of Lukaku in the summer of 2024, but Napoli only paid £30 million for his services. So, all told, the Blues lost £67 million – plus salary payments (rumoured to be £325,000 per week) – on the player, which is an unmitigated disaster given his paltry return on the pitch.
Kepa Arrizabalaga
This might seem harsh to some Chelsea fans given that Kepa has played his part in some success at the club; notably the Europa League campaign of 2018/19.
But the Spaniard was signed as the most expensive goalkeeper in history, and after losing his form he was replaced in the starting eleven by Edouard Mendy.
He’s shown glimpses of quality since, but season-long loan spells at Real Madrid and Bournemouth since 2023 would suggest that his time at Stamford Bridge is limited.
Having paid £71 million for him, it’s likely that Chelsea will take a huge hit if he leaves in the summer of 2025… worst still, if he hangs around until the end of the 2025/26 campaign, Kepa can walk away from the club as a free transfer.
Tiemoue Bakayoko
In terms of pure monetary loss and ROI, the tawdry tale of Tiemoue Bakayoko is right up there with Chelsea’s worst moments.
Some £40 million was shelled on the Monaco midfielder in the summer of 2017, but by June 2023 he was being kicked out of the door for free as his contract came to an end – with just 43 appearances in the blue shirt in the interim.
Bakayoko looked to be a world-class midfield general when he joined the club; a more athletic version of Claude Makelele, was one lofty claim. But he didn’t take to life in London and was loaned out to AC Milan (twice), Monaco and Napoli.
As a measure of how far Bakayoko fell, his next club after Chelsea was Ligue 1 strugglers Lorient. He has since joined Greek outfit PAOK, where he remains (at the time of writing) at the age of just 30.
Danny Drinkwater
There’s a case to be made for Fernando Torres to appear in this slot, given that he was a British record transfer when he joined the Blues for £50 million in January 2011.
The Spaniard did flatter to deceive in his time at the club, but he did score notable goals in Champions League semi-finals and Europa League finals… so there was at least some ROI in his case.
But not so Danny Drinkwater, who was signed from Leicester City having had just one good season… and he promptly flopped.
The £35 million man was an integral part of the Foxes’ shock Premier League title win in 2015/16, but he struggled to bring that midfield dynamism down to the capital with him.
So out of depth was Drinkwater that he only played 22 times for Chelsea, before being banished to feature as an overage player in youth football – where he saw red, literally and metaphorically, after kicking a 16-year-old against Tottenham.
Drinkwater retired from football when his Chelsea contract ended, aged just 33.