5 biggest transfer mistakes made by Manchester United under Ed Woodward

Manchester United are trying to sign Jadon Sancho from Borussia Dortmund but an agreement looks set to remain elusive. With no other significant signings made as yet, could Manchester United be going back to their days of handling business poorly in the transfer window?

They certainly had 2 decent transfer windows in the 2019-20 season. But before that, post the Sir Alex Ferguson era, Manchester United have been infamous for their reckless spending. Not only have they spent carelessly at times, but they have also struggled to sell their players for a decent amount of money.

They have also let go of players who could have definitely had a future at the club. Let's take a look at the 5 worst transfer mistakes Manchester United made under Ed Woodward.

#5 Selling Wilfried Zaha and Memphis Depay

Memphis Depay

Both wingers weren't extraordinary at the time when the Red Devils sold them. Zaha was still trying to break into the first team and Depay had flattered to deceive and his erratic streak was getting in the way of United's progress. However, they were also playing for managers who weren't keen on keeping them.

Both Wilfried Zaha and Memphis Depay moved on and developed into prominent players for their sides. Zaha was sold to Crystal Palace for an initial fee of £10 million rising to £15 million with add-ons. Depay was sold for an initial fee around £16-17 million to Olympique Lyon.

Zaha and Depay are both pacy customers who would have absolutely loved to play under Ole Gunnar Solskjaer. As such, management decisions combined with poor recruitment policies led to United losing two players who would have come in handy when the team finally hit a green patch.

#4 Manchester United signing Bastian Schweinsteiger, Morgan Schneiderlin and Radamel Falcao

Bastian Schweinsteiger and Morgan Schneiderlin

To set the team up for Louis Van Gaal, Manchester United bought an array of midfielders, two of them being Bastian Schweinsteiger and Morgan Schneiderlin who ended up contributing little to the Red Devils' cause.

They were both announced on the same day and the deals ended up being a colossal waste of money. Schweinsteiger endured a testing bout of disrespect too when Jose Mourinho took over and the Portuguese manager decided to send him to train with u-23 owing to fitness concerns.

After a below par debut season, Schneiderlin started just 3 games in his second one before being sold to Everton in the January transfer window of the 2016-17 season.

Both Schweinsteiger and Schneiderlin were ill-advised acquisitions and Manchester United could have very easily spent that money on young prospects.

The less said about Radamel Falcao's dismal loan stint at Manchester United, the better.

#3 Henrikh Mkhitaryan

Mkhitaryan failed to be the creative presence that United were looking for and was poor defensively

Henrikh Mkhitaryan was never going to fit Jose Mourinho's plans for Manchester United. He is not someone who is keen on getting back to defend and was always going to struggle to become a part of a Mourinho low-block. However, it has to be said that Mkhitaryan was coming off the back of an excellent Bundesliga season for Borussia Dortmund.

Mkhitaryan took a long time to settle down at Old Trafford and finally became a mainstay for them in the Europa and league and proved to be pivotal in their cup triumph. However, though he started off on the right foot in his sophomore season, his contributions dwindled to a trickle quite soon.

Mkhitaryan became a shadow of the player he used to be and the Armenian who was bought for £30 million was included in one of the worst swap deals in Premier League history involving two high-profile players.

#2 Angel Di Maria

Angel Di Maria

Angel Di Maria is an excellent player. He was surprisingly offloaded by Real Madrid in the summer of 2014 after he was arguably their best player of the 2013-14 season. However, Manchester United manager Louis Van Gaal had no idea how to use the Argentinian.

Deploying him out wide at first and leaving him to work his magic, Di Maria flourished in the opening few weeks of the season after joining Manchester United for a whopping £59.7 million. A lot of positional changes hampered Di Maria's flow and Manchester United crumbling as a team did not help.

However, Di Maria still registered 12 assists in the league that season. Manchester United should have tried to keep him or at least managed him better. But they sold him after the season was over for a loss of £16 million. Thus Di Maria joined Paris Saint-Germain and has now become one of the most important players for the Ligue 1 champions.

The indecisiveness and short-sightedness of the Manchester United top brass meant that there was no long-term plan and they were simply moving from one manager to the next and from one philosophy to another in a reckless manner and Di Maria was a victim of that among other things.

#1 Alexis Sanchez

Alexis Sanchez

The costliest mistake of them all. Alexis Sanchez was close to signing for Manchester City before the Red Devils decided to hijack the deal. After wreaking havoc for Arsenal, scoring 80 goals from 166 games, he was available for a cut-price deal but his wages were going to be ridiculously high.

The move was not going to benefit Manchester United. The Red Devils already had Anthony Martial and Marcus Rashford playing down the left wing and Sanchez's arrival was only going to impede their growth. But Mourinho decided to demote the youngsters and make an underperforming Sanchez the regular starter.

The Chilean was paid wages in excess of £300,000 per week and Ole Gunnar Solskjaer had no use for him once the Norwegian took over. But United couldn't sell Sanchez and hence they loaned him out to Inter Milan whilst still paying his wages.

Manchester United finally sold him to Inter Milan earlier this transfer window and thus put an end to paying him to not play for the club. It was going to take something quite special to beat the likes of Fellaini, Schweinsteiger, Schneiderlin, Mkhitaryan etc. as the worst transfer story in the post-Ferguson era, but the Sanchez signing definitely tops it.