It was so close. Daniel Levy cut it fine. Having sold Luka Modric with just days to spare in the 2012 summer transfer window, the time to sign players was fast elapsing.
Even then Tottenham chose to leave much of it until the very last day, shipping out Rafael van der Vaart too, and signing goalkeeper Hugo Lloris.
With Moussa Dembele signed a day earlier, there was a growing belief that if Spurs could actually close another midfield target they may actually have entered the window with a stronger window than when they started.
Then the news broke. Porto had accepted a deal for Joao Moutinho, rumoured to be in the region of £25 million.
This was a real player. A midfielder who had impressed at Euro 2012, and proven himself under manager Andre Villas-Boas at Porto.
Finally AVB may get his own man.
But the deal collapsed in the final hours of the transfer window. The explanation given was that the negotiations with a third party were too complex to be completed in too short a time. Spurs had left it too late.
Now in the wake of AVB's sacking, The Telegraph have shed new detail on the talks, claiming a disagreement oer a very small percentage of the overall fee was responsible for the deal collapsing.
They report: "The failure to sign Joao Moutinho at the 11th hour as his replacement – after apparently haggling over €500,000 on a €31 million (£26 million) bid – and it rarely improved after that.
"Villas-Boas was devastated not to acquire Moutinho and believed that he struggled to get any of the players he wanted signed by Spurs."
If true then it's a really sad indictment of Daniel Levy who they describe as a 'numbers man', failing to see the bigger picture.
With Moutinho in the squad, surely Tottenham would have picked up the two points needed over the course of the season to overhaul Arsenal and land in fourth?
You could say Spurs would still have contrived a way to throw it away, but if Moutinho really was the difference make AVB felt him to be, just how miniscule would that £500,000 have been in comparison to the fees the club would have earned from finishing in the top four?
image: © goulao