Football365
·19 March 2026
Five massive Man Utd contract mistakes amid calls for Casemiro extension

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·19 March 2026

The Manchester United of old would already have Casemiro tied down to a three-year extension on double his money. They have made some awful contract decisions…
With Casemiro in fine form, there are calls for United to talk to the veteran about staying beyond the end of this season. It’s a bad idea.
But United have plenty of form for terrible ideas when it comes to renewing contracts, even without mentioning the massive deals given to David De Gea and Marcus Rashford.
Here are five for starters…
Just one of the things Jose Mourinho was right about…
In his fateful final summer in charge at Old Trafford, the start of the dreaded third season when things always unravel for Mourinho, the manager wanted Martial out. For many good reasons.
But Martial had friends in higher places even than Jose. The Frenchman was said to be Joel Glazer’s favourite player and the bean counters seemed to feel they recognised world-class potential more than the fella charged with harnessing it.
Rather than sell as Mourinho wanted, they triggered a one-year option while immediately opening talks over a new deal. Which concluded with Ole Gunnar Solksjaer overseeing Martial’s signature on a four-and-a-half-year deal, while Mourinho was far away, probably thinking United and Martial were welcome to each other.
United’s thinking did not look as daft in the first year of the new arrangement as it did through the remaining three and a half, through which they were obliged to pay Martial a million quid every four weeks.
Mourinho was rather more keen to approve a new contract for Marcos Rojo in 2018. He got that one wrong.
The fact he was limping when he walked to the table to sign the deal should have served as a warning that what United were doing was a mistake. Rojo could be a decent defender, but he regularly made wild decisions. Which may or may not be behind his dreadful injury record.
The Argentina centre-back managed 13 appearances in the two-year period between putting pen to paper and being sent to Estudientes on loan in 2020. Shortly before his terms expired, Boca Juniors took him off United’s hands for an undisclosed fee. If United recouped more than the cost of his airfare, we’d be surprised.
There was a period when United appeared utterly terrified of letting any contract run down, preferring instead to renew under the pretence of ‘protecting their assets’. Even when they are dealing with a liability.
That’s a harsh label to pin on Jones but the ex-England defender’s injury issues made him exactly that, at least from a financial standpoint.
The warning signs were there. Jones had never managed to feature in 30 Premier League games in a season, and after he put pen to paper on a new four-and-a-half-year deal, he appeared only 13 times in the league while pocketing £100,000 a week.
Everyone was a little drunk on Ole Gunnar Solskjaer in February 2019, and you can’t blame the Red Devils for being dazzled by Fergie’s earlier assertion that Jones could become ‘one of the club’s greatest-ever players’ but that very clearly was not on the cards when they gave his agent everything and more in February 2019.
Ed Woodward didn’t catch on quick, did he? He and United repeated the same mistake they made with Rojo and Jones with another centre-back in April 2021.
Bailly was basically the Ivorian Rojo in that he was occasionally decent, sometimes hilarious, often reckless, but more regularly than anything else: injured.
Mourinho’s first signing managed just 37 Premier League appearances in the four seasons leading up to signing for another three years in April 2021. Just to be sure, United made sure they gave themselves the option of an extra year.
To the surprise of no one except Woodward and his pals, Bailly played only eight more league games for United. He spent year two of the three years at Marseille on loan, before United gave him to Fenerbahce for nothing just to get him off the books a year early.
The Portuguese international managed only seven starts in Sir Alex Ferguson’s final term but David Moyes was delighted when less than a month into the first post-Fergie season and the final year on Nani’s existing deal, the winger signed a new contract.
“I’m really pleased Nani has re-signed for the next five years. I’ve been impressed with his approach to training and look forward to working with him in the coming seasons.”
Almost none of the things necessary for that to transpire actually panned out. Moyes was axed the following spring, while Nani managed only a dozen more Premier League appearances for United.
He was loaned back to Sporting for year two of the five United committed to. Of course, the Red Devils paid his salary in full, even if they recouped that from Fenerbahce when the Turks took him in 2015.
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