How football’s £100m men have fared as Chelsea close in on Moises Caicedo

Trying to keep up with this transfer window has become a largely impossible task of late, but one thing seems likely – thanks to Liverpool’s £110m bid, Brighton’s Moisés Caicedo will probably become the second £100m player of the window after Declan Rice.

Now Caicedo may well not be going to Liverpool, as reports at the time of writing suggest he strongly prefers Chelsea, but the numbers will probably line up to make him the twelfth player in history to break that particularly pecunious barrier one way or the other – but is spending such a colossal amount of cash necessarily wise?

Today, we’re going to take a look at the ten players who cost at least £100m before Rice and, maybe, Caicedo, and see how they stacked up after their big-money moves, because there are, frankly, quite a few flops in there – and at least a couple that the clubs involved may be regretting right now regardless of the players’ individual success. Mixing football and money doesn’t always go well, after all…

Before we get into our little review each of the ten most expensive transfers in history, by the way, a tiny bit of housekeeping – we’ve rounded the transfer fees from euros to pounds very approximately to take into account fluctuating exchange rates and all that jazz. These amounts aren’t absolutely exact or on the nose, and also assume every add-on was fully paid, which in at least a couple of instances is surely not the case. We do hope that mollifies any easily-irritated chartered accountants who happen to be reading. This is 3 Added Minutes, not the Financial Times.

Neymar – Barcelona to Paris Saint-Germain, 2017, £190m

The most expensive transfer in history and the one that kicked off the carnival of absurdity that is the modern transfer window. When noveaux-riche PSG chose to make their statement signing by paying off the Brazilian forward’s wilfully stratospheric release clause, they completely rewrote the rules of the game – and turned it into one that could only be played by the obscenely rich.

Regardless of that, Neymar has undeniably been a great goalscorer for PSG, racking up 118 goals in 173 games. Whether you can justify nearly £200m with any number of goal contributions is up for debate, of course, but there’s no questioning his quality. Then again, he never delivered the Champions League trophy that has become the entire point of the PSG exercise over the last six years. But then, hey, neither did anybody else, so that’s more the fault of the club than the player. And now Neymar could well be on his way out, supposedly left out of new manager Luís Enrique’s plans and seeking a move to Saudi Arabia or the MLS after his own supporters starting hounding him at the gates of his own home. Had the expectations been any more normal, Neymar would have been an unqualified success. But as they goal was the moon on a stick, it’s hard to say he was worth every last cent.

Ousmane Dembélé – Borussia Dortmund to Barcelona, 2017, £130m

The problem that Barcelona had, having earned their colossal windfall from Neymar, was that every other club knew that they could extort them for absolutely ridiculous fees. So it was that a 20-year-old Dembélé, undeniably talented but only 22 goals into his professional career, suddenly cost an eye-watering sum that was surely about £50 or £60m more than he was worth to anybody else.

Now Dembélé (perhaps football’s most unlikely childhood Leeds United fan) is seemingly moving on after six seasons at Barcelona, during which he registered 40 goals in 185 games, three La Liga titles, a World Cup win and more injuries and allegations about his attitude than you could shake a stick at given all day. Depending on who you ask he’s either a fabulous player cruelly derailed at times by fitness concerns, or an overpriced, workshy winger who failed to live up to his billing. Either way, PSG fans will be next to make a judgement after the French club triggered his release clause of €50m – less than a third of what Barcelona paid for him in the first place. And apparently the Frenchman’s agent gets half of it. Even Dembélé’s biggest fans must concede that this has not proven to be the best bit of business by Barça.

Kylian Mbappé – Monaco to Paris Saint-Germain, 2017, £155m

Technically, PSG’s other statement signing only joined permanently in 2018 as he originally arrived from the south of France on loan. But the deal was minted in the same summer that Neymar made his way to the Île-de-France and the footballing world was spun on its financial axis, so let’s not quibble.

And honestly, the same combination of praise and caveats applies to Mbappé as it did to Neymar – an unquestionably brilliant player, scorer of countless magnificent goals, who has established himself as one of the very best on the planet. But still, no Champions League and now another extremely expensive departure for PSG, especially when you factor in the colossal signing fee that PSG gave him to stay after the great contractual dispute of 2022, only for the French superstar to turn around and play the same game a year later. May well have cost the club more than Neymar in the long run, without bringing the club any closer to Ol’ Big Ears itself. Still, if you’re going to spend an absolutely farcical amount of money on a player, it may as well be Mbappé. With Lionel Messi and Cristiano Ronaldo safely ensconced in their retirement homes, he’s surely the best in the world.

Philippe Coutinho – Liverpool to Barcelona, 2018, £140m

From Liverpool’s point of view, this may have been the greatest deal in the game’s history – buy a player, have him become one of the best players in your club’s history over the course of five years, sell him for over £130m in profit and then watch his form completely collapse. From Barcelona’s point of view, this was the other massive post-Neymar overspend and easily the worse of the two.

Now struggling to make the first team at Aston Villa, Coutinho’s fall from grace has been absolute. He wasn’t too bad to start out with, but found himself shoehorned into a left-wing role that didn’t remotely suit him – a number ten playing for a club that had no interest in playing with a number ten of any kind. By 2020 he was a pallid shadow of his former self, and a loan spell at Bayern Munich where he won the Champions League wasn’t enough to rejuvenate his career. Eventually sold to Villa for a loss of over £120m. From a purely monetary perspective, unquestionably one of the worst purchases in the history of the game, and one that directly contributed to the club’s current parlous financial state.

Antoine Griezmann - Átletico Madrid to Barcelona, 2019, £105m

Barcelona’s transformation to a tactically pioneering superteam to a strategically inept nursing home for the chronically overpriced was essentially completed by Griezmann, who much like Dembélé was never a bad player, just one who couldn’t feasibly live up to his price tag.

Much like Coutinho, he was essentially forced to play out of position by the presence of Lionel Messi, and while he turned out to be a very decent right-sided forward, it’s very hard to look like you’re worth £105m when you’re essentially relegated to being a peripheral figure by the greatest footballer he ever lived. Has since returned to Átleti for a fee of €20m, another colossally expensive failure by the Catalan club.

João Félix – Benfica to Átletico Madrid, 2019, £110m

Not that Átletico did much better than Barcelona with their own windfall – they uncharacteristically splashed massive amounts of cash on burgeoning wonderkid Félix, who has definitely not repaid the money save for the occasional flash of the talent that drove the hype train in the first place.

25 league goals in four years was definitely not the return the Madridista team wanted for their outlay, and a fairly insipid loan spell at Chelsea last year didn’t suggest that it was simply a question of environment. Now back in the Spanish capital with Diego Simeone extremely keen to flog him for anything he can get, and likely to go down as another big chunk of red in a football club’s ledger.

Eden Hazard – Chelsea to Real Madrid, 2019, £120m

Chelsea weren’t exactly synonymous with shrewd business in the Roman Abramovich era, but did have their moments – and in particular did a great job of selling their Belgian talisman at exactly the right time, moving one of the greatest dribblers and edge-of-the-area goal threats in the game on just before his engine broke. Presumably they learned a lesson or two from Fernando Torres.

Real Madrid thought they were getting one of the greatest wide forwards in the game but instead found that they’d bought his ghost. Four goals in 54 league games in his total return over the last four years, and he’s scored less often than he’s been on the receiving end of jibes about his weight – mostly from people twice his size, naturally. Now a free agent after Real terminated his contract in June, and widely regarded as the worst flop in Real’s history. A sad end for a fabulous player.

Romelu Lukaku – Inter Milan to Chelsea, 2021, £100m

Something closer to Chelsea’s normal business services resumed two years later when they bought Lukaku back to Stamford Bridge for over £70m more than they sold him to Everton for back in 2014. The deal was driven by back-to-back 30-goal seasons in the San Siro but the Lukaku that the London club received was half the play who had left Italy.

Lukaku has had huge peaks and troughs throughout his career and unfortunately Chelsea timed this deal exactly wrong, getting eight league goals for their cash before he was shipped back to Inter on loan – a big disappointment considering that he had registered double figures every year, as a bare minimum, since he left Chelsea the first time around. Somehow his towering physical presence turned into a statuesque one, and Chelsea are left carrying the can as they try to find a buyer – with fans of both Inter and Juventus staging public protests in the hope that their clubs don’t buy him, even at a cut price. Quite a fall from grace for a player who has, periodically, been really quite brilliant.

Jack Grealish – Aston Villa to Manchester City, 2021, £100m

It took a while for the freewheeling Grealish to settle into Pep Guardiola’s exacting tactical plans, and a player used to acting like a one-man team at Aston Villa needed a bit of moulding before he could really settle into his new role as one well-oiled cog in a larger whole – but it seems to have worked, as Grealish became a reliable and important presence in City’s treble-winning side.

His price tag might be even higher than Grealish’s cumulative lifetime bar bill, but he’s definitely made a solid start in the direction of paying it all back – and, unlike PSG’s biggest buys, has actually played a big part in delivering the Champions League to his paymasters. Still a pretty fresh purchase, but looking like a long-term hit so far.

Enzo Fernández – Benfica to Chelsea, 2023, £105m

It’s start far too early to tell whether Fernández will be worth his extravagant fee, but he was one of Chelsea’s better players in a disastrous second half of the season – admittedly a bar so low that it’s more suitable for a limbo competition than anything else.

Much like Dembélé, the Argentine can’t really be said to have played enough games in his life to really justify such a high fee, but had at least won the World Cup and demonstrated a pretty hefty chunk of talent in the process. Probably needs the right midfield partner to realise his potential at Stamford Bridge, and the jury is very much out on this one for now.

So what’s the moral of the £100m stories so far? Well, don’t spend the cash just because you have it. And don’t buy someone for a colossal sum of money when they don’t even fit your tactical scheme. Looking at you, Barça. And Real? Remember to check the warranty next time. Bluntly, it’s hard to live up to such a stupidly high price tag, and few could be said to have managed it. Will Rice and Caicedo be among them? Or is this really just how much a decent midfielder will set you back these days anyway? The heavily-inflated market shows no sign of slowing down, after all, and perhaps in five years’ time the idea of £100m being a lot of money will seem rather quaint. See you then…