Being the super Club they are, Manchester United have been blessed with countless sensational footballers over the years.

The likes of Éric Cantona, Roy Keane, Rio Ferdinand, Cristiano Ronaldo and Wayne Rooney have all graced the Theatre of Dreams in the last thirty years, and depending on who you ask, they could add another handful of names to that illustrious list.

However, like any Club, the Red Devils have also signed their fair share of flops over the years, with perhaps the most extreme example in recent years being Donny van de Beek.

Moreover, what makes that signing even worse is that, just a few months later, the Club were pushing to sign a future superstar but ultimately backed off, potentially believing they already had a player good enough in the Dutchman.

Van de Beek’s United nightmare

In the summer of 2020, United agreed a £35m deal with Dutch giants Ajax for their incredibly impressive young midfielder Donny van de Beek, who just the summer prior had helped the Amsterdam side to a Champions League semi-final and had agreed personal terms for a move to Real Madrid.

Unfortunately for all involved, while it looked like a brilliant deal at the time, it now looks like one of the worst transfers the Red Devils have agreed to in recent history.

For example, in the four seasons he was contracted with the Club, the Dutchman made just 62 appearances, scored two goals, provided two assists, went on two short-term loan moves, and spent a whopping 375 days sidelined with injury.

To top it all off, the 27-year-old was also earning £120k-per-week for most of his stay at the Club and was sold for just £400k to Girona this summer, meaning it was a disastrous move on the pitch and the spreadsheets.

Overall, while United have signed worse footballers in the past, few transfers have worked out quite as poorly as Van de Beek’s did.

This makes it all the more maddening that the Club then passed on a youngster who could have been the perfect upgrade in the January after he signed.

United’s pursuit of Moises Caicedo

Yes, the youngster who could have replaced Van de Beek in the team had United stuck to their guns and signed him back in January 2021 is Ecuadorian international Moises Caicedo, who completed his £115m move to Chelsea last summer, becoming the most expensive transfer in the competition’s history in the process.

However, before he joined the Blues and Brighton & Hove Albion, the Santo Domingo-born star was on the Red Devils’ radar and could have been another addition to the young and exciting squad Ole Gunnar Solskjær was trying to build at that time.

The Norwegian icon confirmed the Club‘s interest in the Chelsea midfielder in an interview with the Athletic last year, revealing that a fear of the youngster’s inexperience prevented the deal from proceeding.

However, a report from the Manchester Evening News at the time claimed that United pulled out of the deal due to too many intermediaries making the negotiations ‘messy,’ which could explain why Fabrizio Romano claimed the potential €5m – £4m – fee was not seen as a stumbling block in December 2020.

Ultimately, whether it was a concern about his perceived lack of experience or the involvement of too many hands in the deal, United decided against signing Caicedo for a minuscule fee in January 2021 and were left with Van de Beek as their shiny new midfielder that season, which has to go down as a massive transfer mistake.