How much is too much? That question would have crossed Liverpool owner John W Henry’s mind on a number of occasions in recent months, not least when, at an in-person meeting in Boston, he sanctioned a big-money move for Florian Wirtz.
The Anfield club are close to pulling off the transfer coup of the summer after beating Bayern Munich and Manchester City to the signing of the German superstar.
After reports revealed that the 22-year-old had chosen to join the Premier League champions, all that was left was to agree a fee with Bayer Leverkusen for the playmaker.
Weeks of negotiating finally yielded an agreement. A base £100m fee, which could rise to £116m depending on bonuses including winning the Premier League and Champions League.
The transfer, which could be completed next week following a medical, will see Wirtz become the 10th player in world football to cost £100m or more. And it’s fair to say many of his predecessors have not fared particularly well.
There are nine other stars to fetch nine figures – but not all have provided a bang for their buck.
Liverpool are closing in on the £116million signing of German superstar Florian Wirtz from Bayer Leverkusen

The acquisition of the 22-year-old is a clear signal of intent from the Premier League champions
Neymar – Barcelona to PSG, £200m
The Brazilian’s 2017 move to Paris ended one period in football’s history and marked the start of another. However, when the monied Ligue 1 club more than double the then-world record £89m fee Manchester United paid to sign Paul Pogba, they would have hoped for more trophies, well, one in particularly.
It is more than a little ironic and well discussed that PSG finally achieved their ultimate goal of winning the Champions League after getting rid of global superstars like Neymar.
But despite never winning Europe’s biggest prize in Paris, it is unfair to characterise his time in France as a complete failure. Neymar was a phenomenon in Paris, racking up 118 goals and 79 assists in 173 matches for the side.
His biggest issue was injury. Ligue 1 defenders had little appetite for his audacious tricks and flicks, which were often met with mistimed or outright malicious tackles. The result was that Neymar missed the defining portion of the season several years on the bounce.
Add in his love for parties and his steadfast commitment to his sister’s birthday and you have one poor deal. The only saving grace for PSG is that they managed to hoodwink Al-Hilal into signing him for £78m in 2023, which turned out to be the worst transfer of all time.

Neymar’s transfer to PSG in 2017 completely broke the market and has forever altered the valuation of players
Kylian Mbappe – Monaco to PSG, £163m
Even PSG couldn’t make the finances of signing Neymar and Mbappe work in the same summer so the Frenchman was initially brought in on a season-long loan in 2017 before completing a £163m transfer the following year.
The fact his fee is rarely discussed seven years on shows the promise of his startling campaign in Monaco has been fulfilled. But it should not go without saying just how ludicrous it was for the Parisians to go so big on a player so young with little first-team experience.
But PSG were proved right, with Mbappe becoming the face of the club, French football and one of the global stars of the sport. His record of 256 goals makes him the club’s all-time top scorer, while his 108 assists means he registered 364 goal involvements in 308 matches.
With numbers like that it’s hard to label his time in the French capital as anything other than a success, even with his tumultuous exit and the failure to win the Champions League.

Remarkably, PSG signed Kylian Mbappe in the same summer as Neymar, initially on a season-long loan

Despite not winning the Champions League, Mbappe become the club’s all-time leading scorer
Philippe Coutinho – Liverpool to Barcelona, £105m
Liverpool fans would despise Coutinho if they did not greatly appreciate what his sale to Barcelona meant for the club’s recent history. It’s not an exaggeration to say that without Coutinho’s exit, there would be no Virgil van Dijk, Alisson Becker and perhaps no Premier League and Champions League trophy.
Of course, Barca were only able to sanction a deal – and be ripe for exploitation – because Neymar had been snatched away by PSG. So in that sense, Liverpool were the biggest beneficiaries on the biggest transfer in history.
While PSG fans will likely cherish some memories from their time with Neymar, the Barcelona faithful are unlikely to have any warm feelings towards the Brazilian, who never managed to settle in Catalunya.
To be fair, Coutinho’s first half season after his January 2018 move suggested he might prove to be a solid addition but his production dried up in subsequent seasons, leading to a loan spell with Bayern Munich in 2019-20 where he scored a brace in an 8-2 quarter-final demolition of his parent club.

Shaken by the capture of Neymar six months prior, Barcelona went big on the signing of Philippe Coutinho
Joao Felix – Benfica to Atletico Madrid, £113m
Atletico took a leaf out of PSG’s playbook and took a punt on an exciting attacker after an impressive campaign domestically and in Europe. But unfortunately for the LaLiga side, they bet on the wrong horse.
Felix is without question one of the most frustrating talents in top level football today, given his unwanted combination of immense talent and regular no-shows.
Six years on from the transfer to Diego Simeone’s side, Felix is yet to find a home among Europe’s elite despite spending time with a host of top clubs. Chelsea took a chance on a loan move in 2023, after he had fallen out with Simeone, but didn’t fancy signing him permanently and he made a temporary switch to Barcelona.
Oddly, the Blues came back in for the attacking midfielder in 2024 but quickly shipped him off to AC Milan on loan but they too have been unimpressed with what they’ve seen.
Still on 25, Felix needs to act quickly to preserve his career at the top level. The fee Atletico paid to sign him seems to have done more harm than good.

Joao Felix attracted interest from several top clubs after starring for Benfica but was snapped up by Atletico Madrid
Enzo Fernandez – Benfica to Chelsea, £107m
Fleecing Europe’s elite for highly rated talent is a practice Benfica have elevated to an art form and their work in the late 2010s and early 2020s was some of the finest ever witnessed.
Six months after signing the midfielder from River Plate for around £15m, the Portuguese giants agreed a £107m sale for the youngster after his impressive World Cup.
The 24-year-old has made a good impact at Stamford Bridge and produced several big moments for the club but at this stage it’s hard to say he’s lived up to the astronomical fee paid to acquire him.
However, there’s still plenty of time for him to fulfill that promise especially with Chelsea returning to the Champions League this season.

Benfica managed to sell Enzo Fernandez to Chelsea for an eye-watering £107m just six months after signing him from River Plate for £15m
Antoine Griezmann – Atletico Madrid to Barcelona, £107m
Another disastrous post-Neymar transfer for the Catalan club saw the French star walk through the doors at the Nou Camp in 2019. Griezmann established himself as one of the best players in the world during his five-year stay in the Spanish capital but he failed to make his mark at Barca.
His tasked was not aided by the financial mess that had begun to engulf the club following their terrible response to Neymar’s departure or the poor fit alongside Lionel Messi.
Griezmann managed just 35 goals and 17 assists in 102 appearances for the LaLiga giants before returning to Atletico on loan ahead of a permanent switch in 2022 for just £17m.
As transfers go, they don’t come much worse than that.

Antoine Griezmann’s 2019 move to Barcelona was another poor post-Neymar transfer from the Catalan club
Jack Grealish – Aston Villa to Manchester City, £100m
The first £100m Premier League player, Jack Grealish finally got his chance with a big-six club in 2023 after tearing it up for several seasons with his boyhood side Aston Villa.
In Manchester, Grealish is much-changed. He still exhibits the mesmerising dribbling ability that made him beloved among fans across the country and the uncanny knack of winning free-kicks that paradoxically made him hated. But his production has never been elite, nor does he appear to have improved in any meaningful way.
His debut campaign was certainly his best, scoring five and providing seven assists from 23 Premier League starts as he played a crucial part in the side’s historic Treble-winning campaign.
But the numbers have only gone in one direction since then, culminating in this term when he managed a solitary goal and assist from 20 league appearances.
Grealish is set to leave the club this summer after being essentially frozen out by Pep Guardiola, being an unused substitute in the FA Cup final and omitted from City’s Club World Cup squad.
I think it’s fair to say that this signing never really worked out.

Jack Grealish enjoyed his most productive and successful season in the year he signed for Man City
Declan Rice – West Ham to Arsenal, £105m
‘Declan Rice, we got him half price’, sing the Arsenal faithful in recognition of the supreme talent they acquired from their London rivals West Ham in the summer of 2023.
Rice has one of the strongest cases on this list to be considered a success. Though, you feel major trophies are necessary for his signing to be firmly established as such.
On an individual level, Rice has been outstanding for the north London club and is coming off his most impressive season for Mikel Arteta’s men. His stand out contribution was a pair of breathtaking free-kicks in the Gunners’ Champions League quarter-final first-leg win over Real Madrid.
Should he be part of the Arsenal team that ends the club’s long wait for a league title or claim’s their first-ever European Cup, many will be echoing that favoured Emirates chant.

Declan Rice has proved to be a major hit in north London since his big-money transfer in 2023

Fellow Premier League midfielder Moises Caicedo completed a mega transfer in the same summer

The 23-year-old has begun to show the form that persuaded the Blues to part with £115m
Moises Caicedo – Brighton to Chelsea, £115m
Two years after their failed attempt to sign Caicedo and break the British transfer record, Liverpool look set to make history with Wirtz. But back in 2023, they were left with egg on their face after an ill-advised late swoop for the Ecuador international.
Brighton couldn’t believe their luck when the Reds entered the bidding for the defensive midfielder after they had failed to reach an agreement with Chelsea. After accepting Liverpool’s offer, Caicedo insisted on his wish to move to Stamford Bridge, paving the way for the £115m fee.
Caicedo made a slow start to life in Chelsea blue amid a rocky first half of the season for the club but he has begun to show the form that made him highly sought after at the Amex.
His performances last term saw him win the club’s Player of the Season and he’s well on his way to making everyone forget about the sum shelled out to take him to west London.