Manchester United splashed £86m on Antony in Erik ten Hag's first transfer window at the club.

Since then, the Brazilian has cost United more than £5m per goal and assist contribution. After being trusted implicitly by his former manager, the winger finds himself at a crossroads ahead of the January transfer window.

Amad has since overtook him in the pecking order and Ruben Amorim appears content for him to be nothing more than a bit part player. That is clearly not what Antony had in mind when he forced a departure from Ajax having bagged 24 goals and 22 assists in 84 appearances.

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With time appearing to slip away from Antony, MEN Sport has looked back at some of the key moments from his United career that have led us to this situation.

That spin

When Antony performed a spin during the Europa League clash with Sheriff Tiraspol in 2022, he would not have thought it would attract so much attention. United still have it plastered on their website as an example of his talents.

But even as we head into 2025, Antony can still be seen trolled online for what many deemed to be a disrespectful act. United great Paul Scholes called him out at full-time after he was less than amused by the moment.

"I don't know what he's doing," the former United midfielder told BT Sport. "It's ridiculous. It's showboating.

"He's not beaten a man, he's not entertaining anybody." Perhaps if Antony had shown the consistency of a Ronaldinho after this moment, things may have played out differently.

This would not be the last time he would be accused of disrespectful behaviour. Antony was widely slammed last season as he appeared to mock Coventry City players after knocking the Championship club out on penalties in the FA Cup semi-final at Wembley Stadium.

His promise

After a disappointing campaign in 2023/24, Antony decided to take the bull by the horns and address the situation with members of the media. Speaking in a Beverley Hills hotel during the summer pre-season tour, the Brazilian made a clear promise.

"I have a lot of objectives, ones I write down for myself and many for this new season," he explained. "I definitely need more goal participations and to score more goals; it’s something I demand from myself.

"Rest assured, you’ll hear the name Antony in relation to goals and assists." This season, he has managed one goal and zero assists in ten appearances.

Ten Hag warning to Amorim

A number of factors contributed to Ten Hag's departure from the club but the signing and subsequent defence of Antony may have played a big role. After the winger picked up an injury against Fenerbahce in the Europa League two months ago, the Dutch manager spoke adamantly about Antony's desire to come good.

"It's really unlucky for him," Ten Hag said. "I feel real compassion for him, when he worked so hard in training.

"His training performances are that good that he deserved to come on. When you have to come off so quickly, that is really sad to see."

Ten Hag was sacked by Ineos less than a week after these comments.