Three of the six most expensive ever moves down the Premier League table have been to Spurs – but the biggest of all might never be beaten.
One simple rule: these are the most expensive transfers in which the selling team finished higher in the Premier League table than the buying club, with a mid-season deal chucked in for good measure.
N’Golo Kante – from Leicester (1st) to Chelsea (10th) for £32m
It is not often a player can leave the popular, newly-crowned miracle champions for a loathed mid-table team with barely an eyebrow raised or an unkind word spoken. But the combination of Kante’s inherent likeability and the Freaky Friday scenario Leicester and Chelsea found themselves locked in a decade ago led to one of the strangest yet most straightforward transfers imaginable.
Chelsea, at the start of their rebuild under Antonio Conte, faced basically no competition for very possibly the best player of the previous season, although Arsene Wenger inevitably fluttered his eyelashes and PSG sniffed around.
Eight players moved to Premier League teams for bigger fees than Chelsea paid Leicester for Kante in the same summer. Arsenal spent more on Granit Xhaka, Spurs invested as much on Moussa Sissoko and Manchester United paid about three times the amount for Paul Pogba. Phenomenal work from all involved.
Alex Iwobi – from Arsenal (5th) to Everton (8th) for £34m
Marco Silva kept a straight face when describing Iwobi as “one of our main targets”, despite the Toffees having to rush through a move in the final two hours of the 2019 transfer window after finally abandoning their summer-long pursuit of Wilfried Zaha.
Iwobi’s future was intrinsically linked to that of the Crystal Palace talisman either way. The Nigerian said he would have to consider leaving Arsenal if Zaha joined the Gunners due to the added “stress” of competing for places, with that pressure enough to evoke panic even when it was only Nicolas Pepe who moved to north London.
Everton had finished 16 points behind Arsenal but in the midst of a period of lavish spending reached up the table to make Iwobi the third-most expensive player in their history at the time.
The gap was actually closed to seven points in 2019/20, with Iwobi a late substitute in an abysmal game watched from the stands by incoming managers Mikel Arteta and Carlo Ancelotti.
Lewis Hall – from Chelsea (6th) to Newcastle (7th) for £35m
A slightly different case: Hall’s marriage with Newcastle was arranged when the Magpies were eight places higher than Chelsea, but by the time that loan was made permanent a year later the Blues were one position and three points ahead.
It is unknown whether or indeed how many of the £7m add-ons included in the deal have been triggered, but 80 appearances, an actual trophy and a handful of England caps will have gone a long way.
Dango Ouattara – from Bournemouth (9th) to Brentford (10th) for £37m
This was a step sideways rather than down in reality. Brentford had finished below Bournemouth by three goal differential points, with both punching well above their weight.
In a restructuring of their pillaged attack, Brentford saw the Premier League experience of Ouattara as key. The forward scored seven goals in 32 games in his last Bournemouth season, then matched that record in his first campaign with the Bees.
Juan Mata – from Chelsea (3rd) to Manchester United (7th) for £37.1m
While Manchester United were officially Premier League champions for a little under four more soul-sapping months, their star had already fallen by the time Mata’s helicopter landed at Carrington.
David Moyes welcomed the Spaniard with unsurprisingly open arms, hoping he could galvanise his fading first season at Old Trafford as Manchester United sat seventh, a point clear of Newcastle.
Chelsea were third at the time the deal went through, much to the chagrin of Wenger. “Some teams have already played twice against one opponent and some others not. I think if you want to respect the fairness for everybody exactly the same, that should not happen.”
He would loan Kim Kallstrom later that month in protest.
Mata, on the other hand, will probably forever remain the top scorer of Ryan Giggs’ entire career as a club manager.
Nemanja Matic – from Chelsea (1st) to Manchester United (6th) for £40m
The first of a great many awkward midfield keys signed to unlock Pogba, it was Matic who Jose Mourinho described as having “everything he wants in a footballer” in what was presumably intended as a compliment but is actually a damning indictment beyond about 2015.
Conte was furious and for once entirely justified as Chelsea used the funds to restock their cupboards with Tiemoue Bakayoko and Danny Drinkwater before Ross Barkley arrived in January.
The Blues fell to fifth in what amounted to a solid title defence considering their previous efforts, beating Manchester United in the FA Cup final after Mourinho secured his self-identified greatest achievement of finishing second to Manchester City and waiting patiently for the title to be reallocated years later.
Cole Palmer – from Manchester City (1st) to Chelsea (12th) for £42.5m
Enough steaming missiles have been launched at the walls of Stamford Bridge, Cobham and any other property Chelsea have sold to themselves over the years for some to stick. Yet Palmer is still probably the one unqualified success story for Clearlake’s recruitment strategy.
How wasteful it would have been had he heard Pep Guardiola out and decided to stay at Manchester City on the promise of a steady increase in minutes. Palmer felt he was already better than the 13 starts afforded to him in two seasons as a first-teamer and backed himself for a lead role elsewhere instead of playing a part in a supporting cast.
Chelsea provided that platform and their sole regret will be that Palmer’s contract only runs for another 427 years.
Jan Paul van Hecke – from Brighton (8th) to Spurs (17th) for £52m
It was a self-described “great step forwards in my professional career”, a move to “one of the most important clubs in England” and a “dream come true” to even just train with Richarlison.
There was little doubt as to whether the Roberto De Zerbi pull existed, but definitive proof of how strong it could be came when relegation-adjacent Spurs reacted to becoming the first Premier League club to finish 17th in consecutive seasons by luring a Europa League qualifier’s defensive leader.
Brighton had quite inevitably finished above Spurs in the previous two campaigns, have won three and drawn two of their last six games against the north Londoners, and offer a far more stable platform for players to develop and thrive.
But Spurs clearly made some absurd promises to De Zerbi that need to be fulfilled.
Kyle Walker – from Spurs (2nd) to Manchester City (3rd)
The game went in the summer of 2017 and Walker was held responsible by many.
The mere concept of a full-back being sold for upwards of £50m caused a thousand think-pieces about the sport’s spiralling finances, followed by weeks of introspection as everyone pondered what part they had played in this and how they could possibly have stopped it.
Kyle Walker. £50m. Entire heads fell off across the country.
Forgotten in the ensuing madness was the fact that Walker had ostensibly taken a step down. He helped Spurs claim the Put The Pressure On Cup, securing his place in the PFA Team of the Year in the process, before being dropped by Mauricio Pochettino for the FA Cup semi-final, a north London derby and a match with Manchester United. Those seven minutes in a 2-1 win at White Hart Lane in May 2017 happened to mark Walker’s last in a Spurs shirt.
The right-back joined Manchester City that summer – for £50m! – and immediately explained that he moved to a team which finished eight points behind Spurs and was knocked out in the last 16 of the Champions League in Pep Guardiola’s debut trophyless season “to go on and pick up silverware”.
Walker left the Etihad last summer with 17 winner’s medals in eight years. Listen, fair play.
Mohammed Kudus – from West Ham (14th) to Spurs (17th) for £55m
It is an unflattering reflection of both club and player that Kudus signed a West Ham contract containing an £80m release clause in the summer of 2023 and left for £25m less two years later.
There were flashes of something exceptional over those 80 Hammers appearances under three different managers, but that wonderful first season being shown tapes of Steven Pienaar by Moyes had faded long before Spurs swooped.
Thomas Frank identified the Ghanaian as his priority signing, Kudus picked out Spurs as the only club he wished to join, West Ham swallowed their pride to fund much-needed squad improvements, and every party involved in that paragraph was considerably worse for the experience.
Bryan Mbeumo – from Brentford (10th) to Manchester United (15th) for £65m
There was indelible proof of Manchester United’s perennial transfer pull when what could have been a summer-long auction between a number of potential suitors was reduced to a staring contest between Ruben Amorim’s side and Brentford.
Manchester United were frustrated but all involved felt they got the best out of a deal which took about two months to construct between the rejected opening bid and accepted third offer.
Manchester United brought Brentford to the table at £55m and left with Mbeumo in tow once the eventual numbers surpassed £70m.
For a player only beaten in terms of combined goals and assists in the 2024/25 Premier League season by Mo Salah and Alexander Isak, it was a fair price for an apparent overpay.
Sandro Tonali – from Newcastle (12th) to Spurs (17th) for £92.5m
It was not in the playbook of Saudi global domination that almost five years into this PIF rule, one of Newcastle’s best players would have their head turned by a team which was roughly another two Igor Tudor caretaker games away from being consigned to the Championship.
But the Big Six is eternal, the aforementioned De Zerbi and London lures are real, and some will never be convinced that Tonali has moved for anything other than that sweet lucre.
Moises Caicedo – from Brighton (6th) to Chelsea (12th) for £115m
The Liverpool copium was remarkably strong when their ambitious midfield transfer overhaul was slightly undermined by the panicked £111m bid Chelsea duly hijacked with a £115m offer of their own shortly after.
Their frustration and consternation was broadly understandable. Chelsea had just finished in the bottom half under Frank Lampard in what was until recently an unthinkably embarrassing crash through the glass ceiling the Big Six clubs installed long ago; Spurs would probably take 12th right now.
Liverpool were far from the peak of their powers, finishing fifth and suffering early exits from the three knockout competitions, but they had Jurgen Klopp and a clear plan moving forward.
That centered around the midfield and when Jude Bellingham inexplicably chose Real Madrid instead, the money the Reds put aside was thrown in the general direction of Caicedo.
Brighton, who ended the 2022/23 just a place behind Liverpool, were happy enough to watch the auction unfold and escalate.
