A car-crash start to 2022/23 saw Erik ten Hag lose his first two games in charge of Manchester United, including that humbling 4-0 defeat away to Brentford.
A sense of panic followed at Old Trafford, with the Red Devils subsequently forking out £70m to prise an ageing Casemiro from Real Madrid, prior to adding fellow Brazilian, Antony, on an eye-watering £86m deal from Ajax.
While the former - now on six goals this season - has certainly come good, the same cannot be said of the latter, with United drastically overpaying for a player who had been valued at just £25m during Ole Gunnar Solskjaer's time at the helm.
Antony-Man-Utd-Sheffield-Utd
Considering the size of the fee, and the winger's eventual return in a red jersey, he certainly ranks highly on the list of the biggest transfer misfires of the post-Sir Alex Ferguson era in Manchester.
Antony's most memorable - or infamous - moments at Man Utd
You can't not mention Antony without remembering his infamous, 'trademark' spin, having been branded a "clown" by Paul Scholes after attempting that novel, ultimately futile, piece of skill in a Europa League clash with FC Sheriff.
As the ball drifted out of play, the tone was set for what was to follow during the young maverick's United career, having initially started brightly with three goals in his first three Premier League games.
Only two top-flight goals would actually follow after that early flurry, with the one-time Sao Paulo man seeing his best moments come in cup competitions, both in Europe and domestically.
Antony - Man Utd record
Competition
Premier League
Europa League
Champions League
FA Cup
League Cup
Community Shield
On the continental front, Antony memorably lashed home in the thumping Europa League win over his future employers, Real Betis, in his debut season, having already got the better of LaLiga opposition in the previous round, after curling home against Barcelona in the play-off stage.
That fine strike was only bettered for drama by the forward's rare right-footed goal to equalise in the FA Cup thriller against Liverpool the following season, taking the game to extra-time as United went on to secure a famous 4-3 triumph.
Even that moment of magic was somewhat overshadowed by Antony's antics in extra-time, however, having reacted furiously to being shifted to left-back as the hosts tried to salvage the game.
In all, just 12 goals in 96 games makes for miserable reading for such an expensive signing, although at least the Brazilian showed flashes of his talent. That isn't the same for everyone.
£50m Man Utd man looks like being the worst post-Fergie signing
Antony hasn't been alone in struggling to meet expectations, with Jadon Sancho's £73m deal also going sour, as too did the £40m investment in Donny van de Beek.
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A number of their additions haven't lived up to expectations.
Questions are also likely to be asked of the decision to fork out £60m on an injury-hit Mason Mount, considering his string of absences since, although the Englishman has at least sparkled in patches, scoring three times from his limited minutes this season.
Considering the size of the price tag, and the lack of impact to date, perhaps the biggest mistake United have made in the market rests with Manuel Ugarte, with the Uruguayan having joined for a total fee of around £50m back in 2024.
Ugarte
Plucked from Paris Saint-Germain, after previously shining at Sporting CP, the South American looked like the natural successor to the veteran Casemiro, with the INEOS regime moving on Scott McTominay in favour of a more defensive-minded addition instead.
It's no secret that such a decision has backfired spectacularly, and while McTominay has emerged as a Ballon d'Or-nominated, Serie A-winning midfielder at Napoli, Ugarte has swiftly faded from view in Manchester.
In 66 appearances to date, the 24-year-old has scored just twice, having only started nine games in all competitions in 2025/26 to date.
Of the seven league games he has started this season, United have won just one of those, suffering hefty defeats to Manchester City and Brentford, alongside the loss at Villa Park, while also drawing against Wolverhampton Wanderers, Burnley and Leeds.
Ugarte stats vs Villa
The drop in quality when he replaces Casemiro is stark, with Ugarte's lack of composure on the ball such an issue, having averaged just 0.1 key passes per game in the league this season, while creating zero big chances.
For comparison, his 34-year-old teammate averages one key pass per game, having created three big chances to date.
Even last term, the supposedly athletic, ball-winning machine was dribbled past 1.3 times per game in his debut season, with Ruben Amorim subsequently admitting that his former Sporting star was "struggling" to adapt to English football.
Much like Antony, Ugarte is now a costly, relatively young signing who United are likely to make a loss on if they do move him on this summer, with this having been another deal that looked set to backfire right from the off.
ugarte-man-utd
Limited on the ball and lacking off it, it's hard to think of many worse signings over the last decade or so.
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