Manchester United’s record in the transfer market after Sir Alex Ferguson is hardly a ringing endorsement for a club’s transfer policy but some misses hurt more than the others.
More than the duds Man Utd signed, sometimes the opportunity cost of signing those players is much more harsh than their signing.
For example, United could have signed Moises Caicedo, offered Erling Haaland, refused to move for Declan Rice, and many more such examples.
Hindsight is 20/20 but in some cases, they seemed like no-brainer moves even at the time and hindsight has only strengthened that feeling that United missed a trick in the market.

Man Utd’s missed opportunity to sign ‘perfect’ duo
Ineos’ pivot towards signing younger players since coming to the club is a nod to the Glazers’ mistake of being too hesitant to do the same.
It can set United up for the next decade but at the same time, loading the team with young players leaves open the possibility of the team just being too raw and aimless in the dressing room.
Tim Sherwood, speaking on Sky Sports’ transfer deadline coverage, said United could have fixed a big problem on the pitch and the dressing room by signing a duo that’s flourishing elsewhere.
The players in question are Harry Kane and Declan Rice, both reliably linked to Old Trafford before they made their big moves.
Sherwood said: “Man Utd missed a trick. A couple of years ago, they missed the ability to get Harry Kane and Declan Rice. Two signings – they would have been cheaper than who they wasted the money on – the 12 to 15 players they bought.
“Those two would have been perfect on the pitch, perfect in the dressing room. They would have got the culture back, a winning mentality and make others better around you.”
Recruitment under Erik ten Hag ageing like milk
It’s easy to look back and think “what if” but in this case, the two players Sherwood named had a genuine chance of joining United only if the club was competent in the market.

United infamously splurged a king’s ransom on Casemiro on deadline day after mindlessly chasing Frenkie de Jong all window on Erik ten Hag’s insistence. Rice left West Ham a year later.
While the failure to sign Rice can be attributed to Ten Hag to some extent, he wanted Harry Kane but it was the one time the board refused his demand and signed Rasmus Hojlund instead.
Basically, Ten Hag was heard when he shouldn’t have been and ignored when he spoke sense, a statement that sums up United’s incompetence under the Glazers.
The result is that recruitment under the Dutchman has conceivably set United back half-a-decade, with expensive mistakes taking years to undo due to ill-advised transfer fees and exorbitant contracts.
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