Ed Woodward has watched two of his long term targets join domestic rivals, which can only leave a bitter taste for the Executive Vice Chairman. Woodward hasn't had the smoothest run since taking over operations of the World's largest football club. However, after what can only be dubbed as a successful summer, which followed a season where United returned to the Champions League, he must be feeling better about life.
It must be tough to be viewed as a pawn in a contract game, as Woodward was with Sergio Ramos and Real Madrid, but seeing two of his top targets join Chelsea and Manchester City must ruffle a few feathers.
Gossip columns were plastered with news that Pedro was about to join United, when Chelsea deployed the same sneaky tactics by swiping their prized target from underneath their noses. Chelsea deployed the same tactic, with Willian set for Tottenham, before signing at Stamford Bridge.
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Worse still, Pedro has taken to life well in the Premier League and looks like he's integrated himself very well into Chelsea's squad. Otamendi on the other hand, is yet to feature for their Manchester rivals, but once again was stalked for a long time by Woodward, before he signed for their neighbours. However it has now been reported that Otamendi was never a target of United, according to Sky Sports.
That information is yet to be verified by officials at United, but the fact is that two great signings have slipped through the fingers of Manchester United. Since Ed Woodward succeeded David Gill, there have been many more stars who have ended up playing their football elsewhere.
Leighton Baines (Summer 2013)
It wasn't a good summer for Ed Woodward. Trying to persuade Bill Kenwright of Everton to part with both Baines and Fellaini for a fee of £36million was quite ambitious. Instead he signed the latter for £27million which shows how unbalanced the deal was.
It seemed like Baines would have been a top signing for United, being a proven Premier League player and a replacement for Patrice Evra. He is an England International, unafraid to push forward and a dead ball specialist. Yet the deal never materialized.
Looking at what was most important for United at the time, I think they opted for the wrong player in the double deal. Sign of things to come for Woodward and Moyes, with the latter getting the chop after 11 months in charge.
Since then the club have signed Luke Shaw from Southampton and Woodward was never asked by Van Gaal to go back for Baines.
Thiago Alcantra (Summer 2013)
One of two attempts for an acquisition of a Barcelona midfielder in 2013. Alcantra is unproven in the Premier League but being young, passionate and full of flare, he may well of hit the ground running with the Red Devils.
One question mark over the transfer which never was, would be the persistent injury problems. Yes he would have galvanized the United midfield line, but not if he plays 18 games a season maximum.
Despite all of this, the deal looked set to be done, but the chance to work with former boss Guardiola at Bayern Munich was too tempting for Alcantra. Goodbye Barcelona! Hello Munich! No Chance Manchester!
Cesc Fabregas (Summer 2013)
The other attempt of luring a Barcelona star, was for a name we all recoginse and once again, all the eggs were put into one basket. The Catalan, who emerged from the famous Barcelona Academy, made a name for himself at Arsenal, before he returned to Spain.
Finding first team opportunities few and far between, thanks to Barcelona's star studded line up, a move back to the Premier League was all too appealing. He was sensational at Arsenal, which earned him the move back home, but Fabregas wants to play football. With Scholes and Giggs retired, the Catalan youth product would have filled the void nicely.
Once again, United lead the chase after Arsenal ruled themselves out of the running, but Chelsea snapped him up instead. London seemed more glamorous that the north west, which seems to be a trend among many European footballers.
Fabio Coentrao (Summer 2013)
Moyes was desperate to replace Patrice Evra, when the Frenchman moved to Juventus. Having failed in the pursuit of Baines, Ed Woodward was also unable to deliver this Portuguese replacement.
Again, it looked likely to be a good signing, but many fans would have been apprehensive about his lack of Premier League experience.
It was understood that a season long loan deal was in place, ready to be completed, only for it to be rejected as it didn't go through before the deadline. Not the best display of time management by the Executive Vice Chairman. What a bad summer for the Moyes-Woodward coalition.
Coentrao has now moved on to Monaco on loan this year, so all's well that ends well!
Mats Hummels (Summer 2014)
Desperately looking for a someone to plug the hole, which was known as Manchester United's defence, Hummels was targeted. It was reported that a move to the Premier League appealed to the German.
The German international was a sought after player. A great man manager of his defensive line, as well as being a perfect blend of brave and tough, it was exciting times according to the tabloids.
However a deal didn't materialise, with no real explanation to why. Hummels is still with Borussia Dortmund, not playing Champions League football, not working with quirky manager Jurgen Klopp and not rumoured to be leaving any time soon. How strange?
Toni Kroos (Summer 2014)
Contract disputes between Kroos and Bayern Munich was the reason why the German international left the Bundesliga Champions. United were in the picture to sign him and at £24million, was a bargain by modern day standards.
Another midfielder which would have given an ora of consistency, which Giggs and Scholes would have usually done. Bayern were willing to sell, once again it seemed like the stars were aligning.
Then the Galacticos came calling and United were edged out of a transfer by Real Madrid. Benzema, Isco, Kovacic and Odegaard were all linked to the Premier League before they moved to the Bernabeu. There are some things money just can't buy.
Gareth Bale (Summer 2013...and 2014...and 2015)
Probably the biggest miss for Woodward and United was watching Bale get on a jet plane and head to Madrid. That was Woodward's marquee signing, to show a statement of intent and the ability to attract megastars to Old Trafford.
The World record fee was in place, but it is understood that Woodward was willing to not only match, but beat Madrid's offer, to land his Galactico. However the chance to compete for trophies in a warmer location was too much to resist for the Welshman, not to mention teaming up with Cristiano Ronaldo.
If you believe the papers, you will see that Bale is constantly linked with a move to Old Trafford every year, so therefore, he is a missed target for the past three seasons! However, if you want the honest truth, then Bale was another miss during that woeful summer of 2013.
Since then, Woodward has stepped up his game and signed an array of talented individuals as he attempts to rebuild United with the help of Louis Van Gaal. 17 players have come in and even more have left during the three summer windows Ed Woodward has been in charge, lets see if he has one more trick up his sleeve before the transfer window slams shut.
United Fans, do you think Ed Woodward has steadied the ship? Or is he continuing to miss out on deals for quality players? Have your say below