There have been frustrations within the corridors of power at Old Trafford down the years about the so-called “Manchester United tax”. In other words, clubs hiking up the price on their players simply because it is United registering an interest. The starker reality, though, is this a problem of United’s own making.

They have demonstrated such an enduring willingness to pay over the odds for transfer targets that rivals can see them coming from miles away and there is no better (or bleaker) example of that than the £85.5 million signing of Antony Matheus dos Santos.

United’s current financial challenges, in truth, are down to more than a single transfer failure. The problems are the consequence of a decade of mismanagement in the market. Make expensive mistake after expensive mistake and eventually there will be reckoning, especially in a new era of cost controls.

But there is also little escaping how damaging the Antony deal – the second costliest in United’s history and at the time the 13th most expensive in football history – has been.

As the Brazilian flop prepares to complete a loan move to Spanish side Real Betis until the end of the season, it is clear the winger’s move from Ajax in September 2022 is a significant factor in why United now find themselves in financial handcuffs and grasping for headroom.

Caving in to pressure

Revisiting that transfer almost 2½ years on, the mind boggles as to how a deal in which United paid £30 million above their initial upper-price limit was ever sanctioned. Even by United’s troubled recent standards, it is jaw-dropping, all the more so given how they had made such a big play going into that summer about the end of the days of being held to ransom.

During the latter stages of Ole Gunnar Solskjaer’s reign as United manager, Antony had been valued at around £25 million to £30 million by the club’s scouts.

Old Trafford sources have always maintained the winger was on their radar even before a deal was agreed in April 2022 for Erik ten Hag – who at that stage was still working with Antony at Ajax – to take over as manager at the end of the season.

At the start of that summer, United set an upper-price ceiling of €60 million (£55 million at the time) for Antony. Leeds’ valuation of Raphinha, who would leave Elland Road for Barcelona in mid-July of that summer for £55 million, was cited as something of a benchmark. The pair had a similar number of caps for Brazil and were competing for a similar position in the team back then.

Yet that overlooked the fact that Raphinha was 25 at the time, more experienced and had proven he could do it in the Premier League having spent two seasons in England’s top flight, during which time he scored 17 goals and claimed 12 assists in 65 appearances. He is now excelling with Barcelona, with 20 goals in 29 matches already this term.

So United’s upper valuation of Antony, from the outset, was already excessive. What then unfolded over the course of two months was quite extraordinary as the club’s executives and the Glazers caved in to an assortment of pressures.

Ten Hag had been clear all along he wanted a right winger and that Antony was his first choice. United had initially appeared reluctant to do a deal after Ajax let it be known that they would not accept €60 million for the player.

It should have been the cue for United to walk away and pursue other targets. But a combination of the pressure applied by Ten Hag, a calamitous start to the new Premier League season and the then Ajax chief executive Edwin van der Sar’s challenge to his old club to go as far as they could resulted in a decision that haunts them to this day – and could continue to do so for a while to come.

By the time they had lost 2-1 at home to Brighton and 4-0 at Brentford in Ten Hag’s opening two games, United had already indicated a willingness to go to €80 million. That in itself smacked of panic but as Van der Sar dug in his heels and demanded more money, United’s resolve gradually weakened as the clock ticked down towards the close of the window.

Behind the scenes, Ten Hag stressed how important Antony was to his plans and way of playing and that he needed a winger who favoured the right flank. There was no one else within the squad, he felt, that was suited to that position.

In the final 48 hours of the window, United relented and agreed to pay an initial fee of €95 million with a further €5 million in add-ons, an eye-watering €40 million uplift. Antony scored on his debut against Arsenal three days later, hitting the first goal in a 3-1 victory, but it would not be the precursor to a thrilling union. Quite the opposite.

To date, Antony has managed just five goals and three assists in 62 Premier League appearances but it tells only half the story of a player who struggles to beat a man on the outside and is alarmingly one-footed.

United fans would soon lose patience with a player who would routinely cut back inside and pass backwards and the brief highlights – the winner in a 2-1 victory against Barcelona at Old Trafford, a dramatic FA Cup equaliser against Liverpool – have been largely forgotten amid the continual underperformance. An abiding image was of Antony performing a 360-degree spin – twice – and then proceeding to kick the ball out of play in a game against Sheriff Tiraspol.

Then there have been the off-field issues, with Antony sent on a period of paid leave last season to fight assault allegations made against him by a former girlfriend. A Brazilian police investigation has since been dropped but a probe by Greater Manchester Police remains ongoing.

Those allegations – which he strenuously denies – affected his form and confidence but they alone do not explain how far he has fallen short of the standards required. He has made just four league starts in 12 months and none since early May last year. Even Ten Hag – who had demanded his signing – eventually lost faith and the Dutchman’s successor, Ruben Amorim, appeared to accept very quickly that the Brazilian was not for him.

Would United have had the money to at least test Tottenham Hotspur’s resolve over Harry Kane in the summer of 2023 had they not spent so wildly on Antony? That is open to debate but they have been saddled with a player signed at exorbitant expense that they will now struggle to sell.

Expensive flop makes it harder to balance books

With his transfer cost spread over the five-year contract he signed, his amortisation cost will stand at £51.3 million by the end of this season – his third year at the club – meaning he will still have a book value of £34.2 million. It is fanciful to think they could attract a fee of that size in the summer, especially with his wages also to take into account, so there could yet be a big impairment hit to come should United seek to flog him for a knock-down fee. A £20 million sale, for example, would mean a further £14.2 million charge in amortisation terms, which would go into the profit and sustainability (PSR) calculations for the year ended June 30, 2025.

Indeed, United’s struggles to sell costly transfer mistakes with little resale value, like Antony and Casemiro, is one reason why the club are now having to give consideration to any offers that come in for the talented academy products such as Kobbie Mainoo and Alejandro Garnacho.

On so many levels, the Antony deal has proven utterly calamitous.