Woodward has almost certainly fed many of the stories to prominent journalists to say that they are ready to walk away from talks, and that other names are in the mix. Ousmane Dembele of Barcelona is mentioned in the latest smoke and mirrors, along with Kingsley Coman and Douglas Costa. These stories can likely be discounted, because the same thing has happened with Leicester City and Harry Maguire, and Crystal Palace and Aaron Wan-Bissaka. Each time United ended up paying the original fee, and cost them time and opportunities elsewhere. It is not the beginning nor end of Woodward’s errors in negotiations.
When Woodward took over from David Gill in 2013, much was made of the fact that he had overseen a ballooning increase in commercial revenue. His masterstroke was to compartmentalise various sponsorship deals to different regions, and to make sure that even tractor manufacturers could be represented by the brand.
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Ander Herrera of Manchester United during the FA Cup Quarter Final match between Wolverhampton Wanderers and Manchester United

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Whether that was a particular insight from Woodward, or an indictment of United’s previously slack monetisation strategy is now largely moot. Instead, there is enough of a track record of his transfer negotiations to call into question his effectiveness. A recap of his past transfer failures would suggest that United fans should continue to worry over their club’s moves in the transfer market until he relinquishes control of the responsibility.
Perhaps the most embarrassing was his pursuit of Gareth Bale from Tottenham Hotspur. Woodward ignored the obvious desire of the Welshman to move to Real Madrid, and offered Daniel Levy an almost irresistible deal: A transfer record for Bale, plus taking striker Emmanuel Adebayor and his wages off his hand. The story goes that United’s executive was surprised to see Bale stepping off the plane in Madrid when he turned on his television.
A more farcical episode goes that during another transfer window, Woodward was kept out of his office as he worked from home to await a broadband engineer. That kind of hands-on attention to detail probably explains United’s other gaffes. During their chase for Juan Mata during David Moyes’ season, United had to employ an intermediary to handle negotiations lest Woodward accidentally cave to Chelsea’s demands at the time and sell them Wayne Rooney.
The previous summer, United turned up in the dying days of the transfer window to sign Ander Herrera, only to be surprised that another set of intermediaries had not left themselves enough time to resolve the intricacies of the midfielder's release clause with Athletic Bilbao, forcing United to deny that the officials had anything to do with them. It ultimately took them a full season to complete the deal, which Louis van Gaal was suspected of approving only because he did not have a meaningful list of transfer targets prepared.
There have been other missteps. Pedro, now at Roma having left Chelsea, was a target for United under Van Gaal and indeed the Red Devils were given an easy run. Barcelona told Woodward that they would happily honour the player’s release clause a year before it kicked in. Instead of taking the chance to strike a quick deal (who can forget United’s insistence they can only manage to carry out negotiations sequentially not simultaneously?) Woodward lowballed Barcelona by a few million. He was warned of another club’s interest and invited to stop messing around, and duly ignored the advice. Believing he had Barcelona on the rack, they simply offered Chelsea the same deal. One could draw a direct line between that error and Jesse Lingard’s substantial and ill-advised United career.

Sergio Ramos celebrates his goal against Mallorca

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There have been other mistakes. Van Gaal was led to believe Sergio Ramos was on his way, only to be reduced to Phil Jones and Chris Smalling. One Jose Mourinho scowl can be attributed to Woodward’s similarly botched chase for Toby Alderweireld. The difference was that Mourinho had learned to discount Woodward's effectiveness by then.
These are just the errors that this writer knows of, but there will be others. With Woodward, another mistake is always on the horizon. Woodward supposedly is keen to be liked, which explains his desire to be involved in the reflected glory that comes with pulling off big name signings, and also the club’s failure to appoint a director of football. If that is the case for Woodward, at some point he must take responsibility for making the same mistakes one window after the next. He probably will still land Sancho, but the only person making it difficult is Woodward himself.

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23/06/2022 AT 06:46