5 greatest players Ed Woodward failed to sign as Manchester United CEO

#3 Gareth Bale

Deportivo Alaves v Real Madrid CF - La Liga

Manchester United were heavily linked with Gareth Bale in the summer of 2013. Ed Woodward provided United with a huge transfer budget as he wanted to bring in big names to the club. David Moyes, who then managed United, had his heart set on Bale, but the Welshman chose to play for Real Madrid.

Gareth Bale was in top form during the 2012/13 Premier League Campaign. He scored 21 goals in 33 appearances for Tottenham and also provided nine assists. Moyes revealed that Bale was the first signing he tried to make at the club. The Welshman might have transformed Manchester United had he accepted the offer.

Bale has won a plethora of trophies with the Galacticos, including four Champions League titles and two La Liga titles. He made his Premier League return to Tottenham in the 2020/21 season, which was sadly quite uneventful. As far as Manchester United are concerned, the Tottenham and Real Madrid star was the one that got away.

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#2 Sergio Ramos

Real Madrid v Manchester City - UEFA Champions League Round of 16: First Leg

One of Real Madrid's greatest defenders, Sergio Ramos was close to joining Manchester United in 2015. The Red Devil’s had made a bid of around £32 million for the Spaniard. The offer was turned down as Madrid valued Ramos at £60 million.

Manchester United had finished fourth in the league the previous season and Woodward needed defensive reinforcements. He believed Ramos could provide solidity at the back and make United title contenders. David De Gea was also part of the deal to lower the asking price for the defender.

Manchester United fans were soon disheartened when Ramos signed a five-year contract and revealed he never wanted to leave Real Madrid. He won three Champions League trophies and two La Liga titles after his contract renewal. The Spaniard was a true leader at Real and was an integral part of their successful European crusades.

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#1 Harry Kane

Southampton v Tottenham Hotspur - Premier League

Harry Kane has been on the transfer radar of many top clubs over the past few years. Manchester United were amongst those interested in the prolific striker. Ed Woodward also mentioned that not being able to sign Kane was one of his biggest regrets.

Tottenham, however, would not let Kane depart quite so easily. Kane signed a six-year contract in 2018 preventing any potential buyers from stealing him away from Spurs. The Englishman is one of the best strikers in Europe and comes with a massive price tag of £150 million. United’s local rivals Manchester City tried and failed to sign him last summer.

Manchester United’s current strike force has a combined age of 70. While Ronaldo and Cavani are undoubtedly still reliable, United will need to find a young and established striker. Kane would be ideal for the Red Devils, but splurging such amounts of money at once would be problematic.