It was a deal that was supposed to have been completed in the final few hours of transfer deadline day. According to Portuguese paper Record, it brought Fabio Coentrao to tears, via Daily Express. The full-back should have been leaving Spain for Manchester United.
In the white corner, Madrid were trying to sign the Granada defender Guilherme Siqueira. This didn't happen, so the Brazilian joined Benfica instead, meaning Coentrao was needed, per Pete Jenson of The Daily Mail.
In the red corner, United were briefing the English press that a deal had been done to bring Coentrao in on loan. Sky Sports even announced it on their news channel. Reports surfaced that they hadn't filled in the necessary paperwork before the 1 a.m. cutoff. Naturally both sides blamed each other. The debacle topped an embarrassing couple of weeks for new Old Trafford manager David Moyes.
Now it seems Coentrao is on the Red Devils' radar once more. Which does pose a number of questions. Do Manchester United need another left-back? Can Real Madrid afford to let him leave? Is the player going to be fit enough over the next four months to make it worthwhile?
Here's how it stands: It's clear that Coentrao wants to leave Madrid and find a fresh challenge. At the right price they will be more than willing to let him leave, but United don't seem keen to buy him during January. Which would mean a loan deal being arranged with an option to buy for a set fee in the summer. Other than four months of not paying his wages, Madrid wouldn't benefit unless a decent amount could be settled upon come May.
But this is a player that hasn't featured for two months following a thigh injury on international duty. He has not played 90 minutes since the Madrid derby at the end of September and only made five appearances all season. Can he stay injury free to make any sort of impact given the problems he has faced this term? Should he make a full recovery, can he dislodge Patrice Evra or adapt to a new country and league in a short space of time? There are doubts from all parties, which is why a deal is yet to materialise.
Then there are the comments of his current boss, Carlo Ancelotti: "hopefully he [Coentrao] will be back playing next week. No one is going out and no one is coming in. We have a very good squad," courtesy of Ian Herbet at The Independent. This, of course, shouldn't be taken as gospel as managers do tend to bend the truth from time to time, but if Ancelotti can't bring in whom he wants, there is no reason to leave himself short.
For Real Madrid, left-back has been a problem position; they have used four different squad members in the role. Marcelo is first choice and has started 11 of the 19 league fixtures but has had his fitness issues. Against Espanyol he made his fifth consecutive league start, the longest run that anyone has held down the spot this campaign.
Young Nacho played there in Gareth Bale's debut at Villarreal, though has featured at centre-back for the majority of his appearances. Right-back Alvaro Arbeloa has appeared on the left side of the defence as many times as Coentrao. If Manchester United and Real Madrid do come to an agreement over Coentrao this winter, be sure Ancelotti will have a replacement up his sleeve.