Comment: David Moyes was playing catch-up in the transfer window at Manchester United – and it showed

The transfer window ended in farce for United, with deals for Ander Herrera and Fabio Coentrao collapsing

David Moyes (right) shows off new signing Marouane Fellaini (Getty Images)

David Moyes must surely have thought he would not have to go through hell twice for Marouane Fellaini.

The full drama of how he and his Everton club secretary Dave Harrison engaged in an deadline night dash to Luton Airport in September 2008, where they literally sprinted down the runway to board Sir Philip Green's private jet and sign him in Brussels, “papers flying everywhere” while Fellaini's two agents argued in French, is told in the autobiography of Mick Rathbone, a long-standing member of his backroom team. Moyes must surely have expected things would be different with all the wealth and allure of Manchester United.

But the chaotic events of Monday night, when Fellaini's £27m signing was not announced until 2am, scrambled that the notion of a smooth succession at the tiller of mighty Manchester United - Moyes and chief executive Ed Woodward effortlessly assuming the tiller from Sir Alex Ferguson and David Gill. There was one element of pre-planning for this transfer window - Wilfried Zaha, the forgotten acquisition, signed in January and loaned back to Crystal Palace - but United's entire transfer market work was essentially packed into the 64 days between Moyes taking over at United, on July 1, and the deadline slamming shut. That spells disaster. Manchester City started planning in October.

In retrospect, you wonder why Moyes didn't quit Everton the day he was appointed and get six extra weeks of Old Trafford badly needed transfer work under his belt. The summer was half over when he arrived, not knowing his new scouts, so not knowing the strengths and weaknesses of the targets - and certainly not knowing about the new top level realm he was operating in rather than be plunged into. In the excellent section on Moyes' Everton set-up within Michael Calvin's book The Nowhere Men James Smith, Moyes' head of technical scouting, saying Everton targets had to be good, Smith says, “but at the same time not so good that they don't want to play for Everton.” Moyes himself admitted a few weeks back that it is a new kind of market he is operating in now.

If that were not challenging enough, United also find themselves with a new chief executive, Woodward, finding his way in a different deal-making environment to the mergers and acquisitions world where he made a name with JP Morgan. Gill was making the necessary introductions for him for months before Woodward succeeded him but it feels like the learning curve will be steep.

The result has been a humiliating, humbing summer by the standards of such a proud club, in which attempts to sign Cesc Fabregas, Leighton Baines and Ander Herrera went south, the noises about luring Cristiano Ronaldo evaporated, a late loan bid failed for a left back - Fabio Coentrao - whom Real Madrid are desperate to get rid of. And Fellaini was signed for £4m more than his Everton release clause which expired in July, as the club engaged in an undignified scramble in the last chance saloon.

The timing and negotiating of some targets has not smacked of Manchester United. The bid for Fabregas went in to Barcelona one day after Thiago Alcantara - whom Moyes didn't fancy - had left gone to Bayern Munich, thus increasing the Cataunians' need of Fabregas. Herrera had been tracked for several years at Athletic Bilbao, with his performances in the club's 5-3 aggregate Europa League defeat of United in 2012 key to their interest. That was long enough for United to know that the Basque clubs always demand the full asking price for their players, because their Basque-only buying policy severely limits their potential to buy replacements. United didn't raise the £26m bid they offered for Herrera late last week, leaving them $4m or so adrift.

Only when the dust settled on a night which lurchd ino absurdism did the full chaos become clear. When a profoundly angered Everton dug their heels in, insulted by the size of offer for Leighton Baines, United pursued Coentrao, whom Real had been touting all summer with Granada's Guilherme Siqueira lined up to replace him. Siqueira waited and waited for Real but when Coentrao couldn't be shifted, Granada packed him off to Benfica. When United made their late move for Coentrao, agent Jorge Mendes went into overdrive, trying to haul Siqueira back from Benfica. Definitely not, said the Portuguese. So Coentrao had to stay where he was. The pursuit of Real's Sami Khedira was less intense. There was an inquiry - no bid, as the player has claimed.

The general rule of engagement in the market like this is that two, three or four active targets will be earmarked for the positions where reinforcements are required. Clubs break rules to get all the groundwork done for perhaps two full-backs - medicals quietly completed, meetings held, terms agreed - so there are backups if the selling club cuts up rough.

United could have bought out of this mess by paying over the odds. Herrera could have been secured for another £5m and Baines for £20m, though it is part of Moyes' Everton character that he has always refused poor value. “If Everton waste 20 million we'll wait a long time to get anything like that again,” Smith told Calvin. “David Moyes spends the money like it's his own.”

Ferguson will be pleased Moyes has stuck to that principle, having always argued that there was no value in the market. But all value has gone in the market. Yet £5m more seems very little for a club of United's commercial might to pay for the box-to-box midfielder. Time will tell but this might be very a long winter.

'Imposters' leave mystery hanging on Herrera

It will go down in the marginalia of Manchester United history as "Impostergate": the story of how four highly reputable Basque lawyers – Rodrigo Garcia Lucas, Alvaro Reig Gurrea, Francisco Salinas Mezquita and Jose Lasa Azpeitia – pitched up at La Liga offices early on Monday evening to help overcome the complexities of the Ander Herrera move to United. They all helped secure Javi Martinez's tortuous transfer to Bayern Munich last season. United denied all knowledge of them – "nobody had authority to represent Manchester United" the club said yesterday, leading to the notion in Spain that they were imposters.

Herrera's agent denied all knowledge of them. They denied anyone knowledge by refusing to talk. The most likely story is that a deal was closer than the clubs would like to say and that they had the four on hand. But their next pay cheque is too valuable to say as much.

Ian Herbert