The bar to clear to make the top ten list of the most expensive summer deadline day Premier League transfers is £35m, thanks to some awful Man Utd deals. 10) Danny Drinkwater – £35m (Leicester to Chelsea, 2017) Clubs will stop spending money to try and make Antonio Conte happy at some point. Napoli will soon discover that not even unwrapping a brand new Scott McTominay can sate the Italian manager’s appetite for drama.
Conte might actually have had a point when it came to Chelsea’s summer after winning the Premier League title in 2017, though. They built on those foundations with Willy Caballero, Antonio Rudiger, Tiemoue Bakayoko, Alvaro Morata, Davide Zappacosta and Danny Drinkwater. That is an impressively poor hit rate.
One of those transfers ended in an actual apology from the player half a decade later , which says an awful lot. Drinkwater started 12 games in five years at Stamford Bridge, last featuring for them in the Premier League in March 2018 before being sent on four different loans, including two underwhelming top-flight spells with Aston Villa and Burnley. The Blues released him in 2022 but Drinkwater did not officially announce his retirement until October 2023.
9) Alex Oxlade-Chamberlain – £35m (Arsenal to Liverpool, 2017) “It would be not fair to put the defeat at Liverpool, where the whole team had a bad performance, on one player,” said Arsene Wenger in December 2017 , the wounds from a 4-0 shellacking at Anfield four months prior having barely healed. Oxlade-Chamberlain was as hopeless as his teammates in that defeat , so much so that he decided to swap shirts permanently four days later. His Liverpool career picked up where his Arsenal one left off, the midfielder debuting for the Reds in a 5-0 loss to Manchester City.
Oxlade-Chamberlain did not start in a Premier League win under Klopp until November, struggling to establish himself in the side. But just as a stumble started to turn into a sprint, the England international was stopped in his tracks by a serious knee injury in a Champions League semi-final. Oxlade-Chamberlain flitted in and out of the first team for the following five seasons before his exit, with 146 games and five trophies in his back pocket.
MORE TRANSFER FEATURES FROM F365 👉 Twenty biggest transfers in the world in 2024 summer transfer window 👉 The 20 best footballers available on a free transfer right now 8) Alex Iwobi – £35m (Arsenal to Everton, 2019) Few players have as much deadline-day heritage as Iwobi, who joined Fulham for £22m in the final hours of the 2023 summer window. But at least the general public were warned then; Everton’s interest in August 2019 only really became known when the fabled deal sheet was submitted hours before the window shut. The Toffees had finally abandoned a move for Wilfried Zaha and eventually sought to move on to someone Marco Silva laughably described as “one of our main targets for this window”.
Arsenal understandably snapped their hands off. 7) Cole Palmer – £40m (Manchester City to Chelsea, 2023) Chelsea had thrown more than enough at the wall since the Clearlake takeover in summer 2022, but only when they made the opportune swoop for Palmer on deadline day 2023 did it actually stick. As usual, almost no-one outside of Stamford Bridge thought it made a jot of sense.
Chelsea were stocked with uber-talented forwards but no actual striker, while Manchester City happily selling a player does not tend to be a positive sign. But even a broken ownership is right once every couple of years and Palmer – who was not even wanted by Mauricio Pochettino and almost joined Burnley or Leicester instead – instantly became the jewel in Chelsea’s crown. 6) Mesut Ozil – £42.
4m (Real Madrid to Arsenal, 2013) It really was quite a remarkable coup. Perhaps our most enduring memory of Ozil until those Arsenal fans flocked to the Sky Sports cameras in the late hours of September 2 and early yawns of September 3 were of the German running rings around Gareth Barry at the 2010 World Cup. That was enough to whet the appetite of a Premier League desperate to replace the star power of the departing Gareth Bale.
As it happened, that was the move which precipitated Ozil’s arrival. Arsene Wenger described it as a “domino effect” that allowed Arsenal – who had previously signed just Yaya Sanogo and Mathieu Flamini all summer – to sneak in at the final hour. For a long old while it was beautiful and often difficult to comprehend, but the stardust had slowly dissipated by the time Arsenal cancelled his lucrative contract prematurely in 2021.
5) Anthony Martial – £44.7m (Monaco to Man Utd, 2015 ) ‘WHAT A WASTE OF MONEY’ indeed. That Daily Mirror back page is dredged up whenever Anthony Martial hits a run of form – it used to happen, promise – but it really was a stunning investment in a completely unproven product at the time.
Man Utd parted with an initial £36.7m for a player whose entire career comprised of 41 first-team starts. That sounds less striking now Chelsea are signing toddlers to 20-year deals at great expense, but it represented a significant gamble at the time.
It was almost worth it for that debut alone. The sudden burst of pace, the footwork, the public assassination of Martin Skrtel, the opening up of the body, the curl into the corner, the Martin Tylergasm – the grand arrival. That remained the zenith of his Old Trafford rollercoaster, which unfortunately included more nadirs than expected.
The clauses in Martial’s deal to take the figure up to £56.7m were described as “very realistic” by Monaco, despite one of them being that he would win the actual Ballon d’Or by June 2019. He narrowly missed out on the award and somehow stayed for another five years after that.
Up until last summer he was the Premier League’s most expensive teenager ever . 4) Thomas Partey – £45m (Atletico Madrid to Arsenal, 2020) The first summer of Mikel Arteta and Edu at Arsenal was quite the ride. The first three signings were Pablo Mari, Cedric Soares and Willian.
The two most expensive were Gabriel and Partey. Absolutely wild. Partey was the fourth-most expensive signing in Arsenal history at the time, rather lazily described by some as Patrick Vieira’s long-awaited successor at first.
Time has informed us otherwise: as good as Partey can be, he is neither a) elite, nor b) a right-back. 3) Brennan Johnson – £47.5m (Nottingham Forest to Tottenham, 2023) Forest later argued – unsuccessfully, as their subsequent points deductions suggested – that they should not have faced FFP charges because they had to delay the sale of Johnson to maximise his value.
Brentford were most closely linked with their academy product but it was Spurs who eventually won the race as the deadline edged closer. The forward had a solid first year under Ange Postecoglou, scoring five goals and assisting ten. A fair few of those were contributed from the bench, which had done little to squash the theory that he might be a better substitute than starter currently.
2) Matheus Nunes – £53m (Wolves to Manchester City, 2023) Pep Guardiola had previously described Nunes as “one of the best players in the world today” but it always felt like the Spaniard’s customary pat on the head of an opponent Manchester City had literally just hammered 5-0 in a Champions League knockout game. The manager himself admitted that assessment was “overexaggerated” when Nunes joined the Premier League champions a couple of years later – and that was before the midfielder barely played in his debut season at the Etihad. There is still no real place for Nunes in this team, nor any serious interest from potential suitors in his signature.
Manchester City, as they do, simply absorbed the sort of catastrophically poor signing which might have derailed other teams . 1) Antony – £82m (Ajax to Man Utd, 2022) One of the great overpays of all time . Ajax had already sold Ryan Gravenberch, Sebastien Haller, Lisandro Martínez, Nicolas Tagliafico and Perr Schuurs to the tune of about £100m so had no financial desire to cash in on Erik ten Hag’s primary target.
But Man Utd just kept pushing and pushing. As Edwin van der Sar, Ajax chief executive at the time, put it: “We would have liked to keep him here one year longer – there was not a dire need to sell him, we had money in the bank – but the fee got so high. We challenged United to go as far as possible.
” And the daft sods obliged, despite their scouting team reportedly delivering a valuation of Antony closer to £25m ..
