Manchester United are set to go into their first summer transfer window without Ed Woodward since 2012.
Woodward confirmed last month that this season would be his last at Old Trafford, with his decision coming hours after the collapse of the European Super League.
It has been suggested that the timing of the announcement was purely coincidental and that he always intended 2020/21 to be his final campaign at Old Trafford.
John Murtough, the club's newly appointed football director, and Matt Judge are set to completely take over transfer dealings after a reshuffle behind the scenes.
The pair will be hoping for a significantly better record in the transfer market than their predecessor has endured over several years.
A slew of costly transfer misses like Alexis Sanchez, Marcos Rojo and Angel Di Maria have hamstrung the Red Devils as they look to return to the pinnacle of the English football.
But it's not only the players that have come to the club that will haunt Woodward, it is the series of high-profile stars that he decided to not sign.
On one transfer deadline day alone, back in 2018, Woodward vetoed a host of transfer suggestions from Jose Mourinho, who was desperate to overhaul his side's leaky defence.
Rapahel Varane, Toby Alderweireld, Jerome Boateng and Yerry Mina were all previously reported to be on Mourinho's wishlist - only for the executive vice-chairman to refuse to pull the trigger on any.
And now, Manchester Evening News suggest that he also passed up the opportunity to sign Ruben Dias, a full two years before he took the Premier League by storm.
Mourinho was an admirer of the Portuguese centre-back and was said to have intimate knowledge of his compatriot due to sharing the same agent, Jorge Mendes.
However, aged just 21 at the time, Woodward and the rest of the transfer board wanted a more proven option.
Dias would eventually join Manchester City last summer, instantly becoming one of the best defenders in the top-flight and helping them to a third Premier League crown in four years.
Meanwhile, current United boss Ole Gunnar Solskjaer remains in the market for defensive help after another season blighted by struggles at the back.
Pau Torres, Jules Kounde and Varane have all been linked, with the Norwegian confirming they will need to be active in order to reel in the Dias-inspired City.
"We're planning as we normally do," Solskjaer said of the upcoming window. "And, as I said a couple of times recently, I hope we're going to strengthen with two or three players we definitely need to challenge higher up in the table. We're still too behind to think it's just going to come by itself."
Solskjaer will be hoping he, Murtough and Judge can set the foundations for a more fruitful trio than the partnerships that have gone before.
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