For INEOS, a regime intending to get to grips with Manchester United’s status as a loss-making enterprise, the potential €100million deal to bring Antony to Old Trafford stands out as a particularly acute example of the kind of lavish spending that has put the club in a precarious financial position.

With the Brazilian now in the Spanish city of Seville, having joined La Liga’s Real Betis on loan until the end of the season, United fans will be left contemplating how a player with such a price tag — £84.1million/$105.1m at the current exchange rate, the second-most expensive transfer in club history behind the re-signing of Paul Pogba in summer 2016 — could deliver just 12 goals and five assists in two and a half seasons.

The truth is United knew they were paying over the odds even at the time, according to sources familiar with the matter, speaking to The Athletic on condition of anonymity to protect relationships.

That awareness can be seen in Antony’s salary, which is akin to that of a mid-ranking member of the squad rather than a star signing. Antony agreed terms worth £140,000 per week for seasons when United are in the Champions League, plus bonuses based on individual performances, but because they are only competing in the second-tier Europa League this term, thus invoking the standard 25 per cent cut for their players, his salary has been around £105,000 a week.

Antony’s representatives had, when negotiating his deal, pitched at £250,000 per week, which would typically be commensurate with a transfer involving such a fee. Securing that would have represented a five-fold rise on what he had been earning at his previous club, Ajax of the Netherlands.

But his leverage in talks with United was weakened because he had told Ajax he wanted the move and, in his attempts to secure it, he stopped turning up for training in the closing days of that summer 2022 window. Figures at United were able to push back in contract talks in the knowledge Antony was desperate to join the Premier League club and they intimated improved terms could be on the cards if he did well, but that he would have to accept entry-level terms at first.

Sticking to a relatively modest salary for a club of their revenue meant United had options when surveying the market for Antony this window. Betis, whose median salary is around £40,000 per week, according to Capology, could afford to push the boat out a little for the 24-year-old. They will cover 84 per cent of his wage at a minimum, plus potential bonuses based on achievements, with only former Real Madrid and Spain forward Isco thought to be earning more than him in their squad.

But the disparity in Antony’s wage compared to his transfer fee, which is still the 18th highest in football history, is evidence of United appreciating that they were paying an excessive amount to Amsterdam-based Ajax even while signing the paperwork.

There was internal pushback over the money involved from people minded to protect the club’s finances and the decision on confirming the move was not unanimous, but senior figures decided they could live with the transfer premium given the circumstances, partly because the salary was not that high. Financial fair play (FFP) regulations and the club’s cash levels were a consideration, but they did not dominate thoughts in 2022 the way they do at present.

Antony was intended to be a starting winger, which would have made the overall cost more palatable, but his status on the periphery of the side for the majority of his time at United has accentuated his enormous cost.

How United got to that point is a case study of everything those now in charge of the club are determined to avoid.

Erik ten Hag’s first summer as Manchester United manager, in 2022, was overshadowed by the failed pursuit of Frenkie de Jong, which coloured conversations for months. The €85million set aside for midfielder De Jong’s proposed move from Barcelona caused a blockage on spending in other areas, with United only freeing up major funds for Ajax defender Lisandro Martinez (in a deal worth £57m) by the time Ten Hag went off on pre-season (Christian Eriksen, a free agent, and Feyenoord full-back Tyrell Malacia were the other signings).

Ten Hag wanted Martinez and Antony from his previous club, but at that stage, Ajax would only sell one and the manager prioritised the Argentina international centre-back.

United had scouted Antony since his days at Sao Paulo’s academy, when he was only 15 years old. Reports to the club at that time said he had very good pace and technique but strongly favoured his left foot and had predictable decision-making. It was proposed he would need to get stronger and develop his weaker right side to succeed in the Premier League.

Antony’s summer 2020 move to Ajax saw United’s European scouts track his progress in the Netherlands, but during Ole Gunnar Solskjaer’s time as manager, some staff still valued him at only around £25million.

His record in the 2021-22 season of 12 goals and 10 assists in 33 games, including the Champions League, put him on the radars of Premier League sides looking for right-wingers the following summer. Liverpool, with Mohamed Salah’s contract up for renewal, had Antony on a list, as did Tottenham Hotspur. The anticipated fee at that stage was regarded as between £40million to £50m. He was also a full Brazil international, having made 11 senior appearances for his country to that point.

Antony had played under Erik ten Hag at Ajax before joining United (Michael Regan/Getty Images)

Midway through that window, United cut off talks with Ajax on Antony and privately communicated they would not pay more than £60million.

United had alternatives for the right-wing role, most prominently his fellow Brazilian Raphinha, who had scored 11 goals in 35 Premier League games to save Leeds United from relegation, but the Old Trafford recruitment team, together with Ten Hag’s personal influence, rated Antony as the better signing, partly due to him being three years younger. In any case, Raphinha indicated he preferred Barcelona and his £55million transfer to the Camp Nou was sealed in mid-July.

Cody Gakpo was another alternative to Antony, albeit he typically operated on the left or up front for another Dutch club, Eindhoven’s PSV. At one point, United looked to bring in both players, as doubts about Cristiano Ronaldo’s future back at the club continued (he would eventually leave in the November).

United agreed personal terms with Gakpo but, in the final days of the window, stopped short of making a bid to PSV as the rising cost of Antony became clear. The following January, Gakpo joined Liverpool in a deal worth up to £44million.

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Player recruitment is an inexact science and there are a multitude of reasons for how signings work out, but comparing Antony’s post-transfer impact with those of Raphinha and Gakpo, who cost their new clubs £14million more in combined fees, is a painful case of sliding doors for United fans. This season, Raphinha has 22 goals and 11 assists in 30 games for Barcelona and is currently ranked second top-scorer in the Champions League, while Gakpo has 14 goals and five assists in 32 games for Liverpool.

Back in August 2022, United returning to the bargaining table for Antony was partly triggered by the continued uncertainty over Mason Greenwood’s availability — on a football level, his absence took away a right-wing option — and more sharply the back-to-back defeats to Brighton and Brentford which kicked off Ten Hag’s reign.

United, with football director John Murtough leading the sporting department, did not want a manager they had chosen after a five-month process to fail. Meanwhile, chief executive Richard Arnold was alarmed at the prospect of missing out on Champions League revenues and the threat of kit manufacturer Adidas cutting payments due to a non-Champions League participation clause. United’s kit sponsorship deal at that time meant Adidas would shave 30 per cent off the £75million-per-year contract for a second season absent from Europe’s elite competition, equating to £22.5m.

Several sources reported a sense of panic at Carrington, the club’s training complex, during those days. Pressure was also being felt from supporters eager to see a new attacker, with Ten Hag pushing to sign a forward.

Antony celebrates scoring against fourth-tier Newport in the FA Cup in January 2024, ending a 31-game goal drought (Athena Pictures/Getty Images)

Arnold and Murtough held talks with Ajax chief executive Edwin van der Sar, bidding €80million, €90m, then €100m. In an interview with The Athletic in November 2022, Van der Sar said: “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. They have a potential world star.”

Ajax stood firm on their valuation, having let five other players leave that summer and being aware that another sale might seriously damage their new head coach Alfred Schreuder. Ten Hag’s replacement lost his job five months later.

Joel Glazer, then United’s co-chairman, was convinced to sanction the spending after seeing how much Antony wanted to join United.

The final terms were €95m guaranteed, with a potential €5m more in add-ons, which are not thought to have been realised.

Antony started well, scoring in each of his first three Premier League appearances, against Arsenal, Manchester City and Everton, and he delivered an excellent winner against Barcelona to crown a stirring European night at Old Trafford in February 2023. In the middle of that season, he started a group game for Brazil at the 2022 World Cup and came on in their quarter-final against Croatia. Ultimately, United qualified for the Champions League by finishing third in the Premier League, going some way to justifying his move.

In the summer of 2023, fellow winger Anthony Elanga was sold to Nottingham Forest for £15million, with his minutes at United restricted.

That September, Antony spent a month out of the squad after police launched an investigation due to his former partner, Gabriela Cavallin, making allegations of assault against him. Antony denied those allegations and similar ones by two other women — Rayssa de Freitas and Ingrid Lana — made in Brazilian media. The case in Brazil is now closed, but as of last week, Greater Manchester Police were still investigating the alleged incidents that are said to have occurred in the United Kingdom.

As previously reported by The Athletic, the potential police action did not show up on background checks made by United before signing Antony.

Antony scored the decisive goal as United beat Barcelona 4-3 on aggregate in the Europa League knockout round play-offs in 2023 (Alex Livesey – UEFA/UEFA via Getty Images)

His form, which had undulated during his first season, hit the skids. He then fell out with Ten Hag over being asked to play left-back.

In February, Ten Hag overlooked Antony for the visit of Fulham, turning to Omari Forson, a 19-year-old academy graduate who was making his first senior start. The next month, Ten Hag gave Antony brutal criticism in the dressing room after his display from the bench in a 2-0 win against Everton, to the extent that the player looked affected.

Antony featured in around half of United’s Premier League games last season, totalling 1,323 minutes from a possible 3,420.

During an interview in pre-season in Los Angeles last August, Antony said that he had learnt from his issues and would look for self-improvement by writing himself notes. By the final stages of Ten Hag’s United tenure in the autumn, he was getting more minutes, notably being sent on ahead of Amad away to Fenerbahce in the Europa League on October 24.

On the sidelines that night, Amad appeared deeply frustrated. Ten Hag defended his decision by pointing to Antony’s performances in training. Given Amad’s emergence to prominence since Ruben Amorim’s November appointment as Ten Hag’s replacement, fans will see another link in the chain reaction of Antony’s arrival.

Amorim tried playing Antony as a wing-back, but his exit now will make room in his squad, and in the accounts, for a new arrival to more suitably fit the new head coach’s 3-4-2-1 system.

United are in talks with Italian club Lecce for 20-year-old Denmark international Patrick Dorgu and are considering triggering the buyback option on Alvaro Fernandez Carreras, 21, who has impressed since moving to Benfica last summer.

United will hope Antony can enjoy a productive loan at Betis to raise his value ahead of an expected permanent summer exit.

At a cost of £82million upon signing, his transfer fee can be spread over the length of his five-year contract, meaning a remaining book value of £34.2m. Getting a club to match that figure, allowing United to offset his price for the purposes of financial regulations, will still be a tough ask.

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(Top photo: Yagiz Gurtug/Middle East Images/AFP via Getty Images)