Neymar has left Saudi Arabia. Antony has flown the coop — at least temporarily — from Old Trafford. Neither deal will be looked back upon particularly fondly.

While the prices were sky-high for both players, it was the performances, or lack of them, that defined their spells at Al Hilal and Manchester United respectively. Neymar struggled with injury during his two-year spell with Al Hilal, making just three league appearances. Antony scored just five goals in 62 Premier League games for Manchester United.

But can either of them be considered football’s worst-ever transfer? Or are there others that stand out as being significantly worse? Neymar and Antony aside, The Athletic’s experts have gone back into football history and picked the standout mistakes below.

Alexis Sanchez, Man Utd

There will have to be a dramatic change in fortunes for Antony to avoid the ignominy of Manchester United’s worst-ever signing, but until the Brazil international is sold, or his contract expires in June 2027, he has time to leave this accolade with Alexis Sanchez.

A swap deal with Arsenal for Henrikh Mkhitaryan meant Sanchez could technically be considered a “free signing”, but five goals in 45 United appearances made for a meagre return.

But it was his wages — thought to be £350,000 per week before bonuses — that tip this deal into the “worst ever” category. Sanchez’s remuneration unsettled United’s wage structure, starting a domino effect of players asking for similar salaries. Such negotiations led to Ander Herrera leaving the club in the summer of 2019 and a huge pay rise for David de Gea, a contract that would later become an issue under Erik ten Hag. It would also have a knock-on effect for contracts handed out to Casemiro and, later on, Marcus Rashford.

Some poor signings only last for the player’s stay at the club. Sanchez’s impact continues to be felt years after he has left.

Carl Anka

Philippe Coutinho, Barcelona

As the token oldie on this panel, I really wanted to pick something from the 1980s, or perhaps from a mad period in the late 1970s, but the sad truth is that the past decade is when football’s transfer market has gone truly insane.

Chelsea and Manchester United alone have numerous contenders for the worst, but I’m inclined to look at that late-2010s period when Barcelona completely lost the plot: Philippe Coutinho for €135million, Ousmane Dembele for €135m and then Antoine Griezmann for €120m. Excellent players, all three — and all had their moments and all won trophies — but the signings were driven by indulgence and excess. The impact on Barcelona’s finances was disastrous and could have been even worse.

The worst deal of the three? I’m going to say Coutinho, who ended up joining Bayern Munich on loan and scoring twice in a humiliating 8-2 victory over Barcelona in the Champions League quarter-final in 2020. What a perfect summary of the super-club excesses of the modern era.

Oliver Kay

Ali Dia, Southampton

“Am I enjoying this? Do you enjoy a kick in the bollocks?” Graeme Souness, then Southampton’s manager, responded in 1996 after being asked about his thoughts on Ali Dia’s Premier League debut.

Dia purportedly claimed he was a cousin of George Weah, the legendary Milan forward, who, allegedly, put in a good word at Southampton. “When someone like that gives you a recommendation, you tend to sit up and take notice,” added Souness.

Dia was woeful and his team-mates had wondered whether he was a competition winner after watching him train for the first time. The saving grace for Southampton is that he arrived as a trialist, saving them a transfer fee, and only had to endure his 53 minutes against Leeds United, which saw him miss a glaring opportunity.

What remains of Dia’s time on the south coast are stories of unpaid hotel bills, fanciful tales told to his team-mates, and proof that anyone can play in the Premier League if they know the right people.

GO DEEPER

‘It was easy to see that this guy had never been close to top level football’ – just how bad was Ali Dia?

Dan Sheldon

Lazar Markovic, Liverpool

Liverpool believed they had signed one of the most exciting youngsters in European football in the summer of 2014.

Winger Lazar Markovic completed a £20million move to Anfield after helping Benfica win a domestic treble in Portugal.

“I can become one of the best players in the Premier League,” he told reporters. “Perhaps I am so confident because in every season I have played I have finished as a ­champion.”

Markovic was very confident when he joined Liverpool (Andrew Powell/Liverpool FC via Getty Images)

Avram Grant, who had managed the Serbia international at Partizan Belgrade, added to the hype as he compared him to Lionel Messi, with the former Chelsea boss declaring: “He’s young, he’ll mature, and then nobody will be able to stop him.”

The reality was very different and Markovic’s name sits alongside El Hadji Diouf, Alberto Aquilani, Andy Carroll and Mario Balotelli when the debate rages over Liverpool’s worst transfer flop.

Markovic’s career on Merseyside included just 34 appearances, three goals, one assist, one red card, four loan spells and a period of training with the under-23s at the academy after being banished from the senior squad.

He never got to grips with the physicality of English football and moaned about the weather on Merseyside. In January 2019, he was granted a free transfer and joined Fulham on a short-term deal. Now 30, he’s playing for FC Baniyas in the UAE Pro League.

James Pearce

Jean-Kevin Augustin, Leeds

Leeds United paid up to £40m for Jean-Kevin Augustin to play 51 minutes for them in 2020. The then 22-year-old was initially signed on loan from RB Leipzig in 2019-20 but with an obligation to buy him for €21m if Leeds won promotion to the Premier League.

Owner Andrea Radrizzani had also agreed to pay Augustin £93,000 per week for five years if Leeds reached the top flight. Augustin had lost his way at Leipzig but was considered one of France’s brightest prospects as a teenager. Director of football Victor Orta hoped Marcelo Bielsa could awaken that form for the Frenchman.

Augustin was unfit and overweight by Bielsa’s austere standards when he arrived and only managed three substitute appearances before he pulled a hamstring and Covid-19 halted the campaign. He tried to mount a comeback for the restart in June 2020, but Bielsa had washed his hands of him.

Leeds tried to argue their delayed promotion, in July 2020, absolved them of the obligation agreed with Leipzig because it was not secured before June 30, as written in the contract. FIFA and the Court of Arbitration for Sport ruled in Leipzig’s favour. United eventually settled a £15.5million fee with the German outfit. Augustin launched his own case against Leeds after that ruling.

FIFA found Leeds were in breach of the contract they originally agreed with Augustin and ordered the club to pay him £24.5m in compensation. An appeal against this decision was eventually dropped by Leeds. It’s unclear if Augustin settled for a lower amount, but Leeds ended the saga with tens of millions spent on a striker they barely got one half of football from.

Beren Cross

Danny Drinkwater, Chelsea

There are so many chapters to this transfer disaster that you could write a book. In theory, Chelsea’s signing of Drinkwater in the summer of 2017 made sense. It gave them the chance to reunite him with N’Golo Kante as the midfield pair who helped win the title with Leicester City in 2015-16.

But the transfer was doomed from the start. Chelsea’s prolonged negotiation over the fee ensured it was not completed until deadline day. It meant the England international missed out on Antonio Conte’s demanding pre-season training drills and, within 10 days of working with the Italian, he suffered a calf injury.

Drinkwater went on to make just 22 appearances that season (12 starts). A 30-minute cameo off the bench in the Community Shield defeat to Manchester City in 2018 turned out to be his last appearance for the club, but he remained on their books for another four years.

Maurizio Sarri left Drinkwater out for the rest of the 2018-19 campaign. He still made headlines. Unfortunately, it was due to being arrested for drink driving after crashing his car.

Loans to Burnley and Aston Villa were more known for him being injured in a fight outside a nightclub, as reported by the BBC, and headbutting his team-mate, Spanish midfielder Jota, in a training session respectively.

Two more loans at Kasimpasa and Reading followed before his Chelsea contract, where he was paid around £100,000 a week, expired in 2022.

Simon Johnson

Per Kroldrup, Everton

Have you heard the one about the Premier League defender who couldn’t head the ball?

Kroldrup arrived at Everton in the summer of 2005 with a lofty reputation; a stylish, ball-playing Danish international centre-back who cost a cool £5million. Yet it quickly became apparent to manager David Moyes and his players that they had signed a dud.

There was one considerable problem: Kroldrup was useless in the air.

“On his very first day, the gaffer took him to one side and started doing heading practice with him, like you would with a seven-year-old,” former team-mate Leon Osman wrote in his book, Ossie: My Autobiography. “It was a case of holding the ball, saying: ‘Are you ready? One, two, three – jump’.

Kroldrup in action for Everton (Clive Mason/Getty Images)

“He had obviously realised that heading wasn’t Per’s strong point. £5million for a centre-half who can’t head the ball..!”

Kroldrup’s only appearance for Everton came in a 4-0 defeat at Aston Villa on Boxing Day. A month later, he was sold to Fiorentina.

Moyes didn’t get many signings wrong in his first stint at Goodison, but this was certainly one.

Patrick Boyland

Eden Hazard, Real Madrid

A record signing from the Premier League being unveiled in front of tens of thousands of supporters at the Bernabeu — the Cristiano Ronaldo parallels were clear when Eden Hazard joined Real Madrid from Chelsea for an initial €100million ($104m; £84m at current exchange rates) in 2019.

But Hazard did not come close to emulating Madrid’s all-time top goalscorer. The Belgian spent four injury-plagued years in the Spanish capital, managing 76 appearances and scoring seven goals. He was never the same after an innocuous challenge from Belgium team-mate Thomas Meunier in a November 2019 Champions League match against Paris Saint-Germain, which led to a series of problems with his right ankle.

Turning up to his first pre-season overweight and having a relaxed attitude to physical preparation did not help Hazard’s image, but it was that ankle injury and the issues that followed that deprived Madrid fans of seeing the barnstorming winger who had torn through opposition defences for fun at Chelsea.

“Real is special,” Hazard told France Football last year. “Afterwards, whether it corresponds to me, I don’t think so. It’s not me. It’s a bit of a show-off club and I’m not really like that… But it was my dream. I couldn’t end my career without going there.”

Hazard terminated his Madrid deal by mutual consent in the summer of 2023, despite having a year left on his contract, and announced his retirement at 32 later that year, writing on Instagram: “You must listen to yourself and say stop at the right time”. It was a sad end to what should have been the crowning moment of Hazard’s career.

Tomas Hill Lopez-Menchero

Xisco or Ignacio Gonzalez, Newcastle United

Worst can be measured in different ways. It could be a waste of money or a squandering of talent or, as was the case at Mike Ashley’s Newcastle United in September 2008, a decision that rippled out and led to disastrous consequences far beyond the impact or otherwise of any signing.

Kevin Keegan, a bona fide legend at St James’ Park, was in his second stint as Newcastle’s manager when Dennis Wise, an executive director, told him that the club were bringing in two new players, Ignacio Gonzalez on loan from Valencia and Xisco from Valencia for £5.7million.

There were a couple of problems with this. Nobody from Newcastle had seen Gonzalez play. Wise told Keegan to look him up on YouTube and later admitted it was “a favour for two agents”. Xisco was another player Keegan (as related in his autobiography) “had never heard of”.

His position “untenable”, Keegan resigned, Newcastle supporters were incandescent, turmoil became engrained and at the end of the most toxic and chaotic season in the club’s modern history, relegation followed. Keegan later won a case for constructive dismissal, in which the club’s evidence was described as “profoundly unsatisfactory”.

George Caulkin

(Top photos: Getty Images)