Spurs chairman Daniel Levy was playing a waiting game with Aston Villa – only for the plan to backfire.
Fierce negotiator Levy was trying to drive down the price knowing Villa’s financial woes were there to be taken advantage of.
But the move spectacularly flopped when Villa welcomed in new owners who blocked Grealish’s exit.
Egyptian billionaire Nassef Sawaris and American Wes Edens have a combined wealth of £40bn – making them the third richest owners in English football.
They have immediately pumped in cash to prevent Villa from falling into administration and have told Grealish he is staying.
A Villa source said: “Spurs could have pushed the button on this two weeks ago before the takeover. They didn’t. And now the owners have said that neither he, nor James Chester, is going anywhere.
“They want to build Villa. That’s not going to happen by selling the club’s best players.”
Mauricio Pochettino admitted Tottenham might not make any signings this summer after criticising the decision to close the transfer window early.
Spurs, who traditionally do their business late, are the only club in the top six not to bring any fresh faces in so far and only have another eight days to do so before the window shuts on August 9.
The decision to bring forward deadline day was voted on by Premier League clubs, who opted to shut the window before the season starts, although it remains open for the rest of Europe.
And the fact Pochettino has failed to land any targets so far has done little to help his mood, with the Argentinian having already complained about the early start of the Premier League season after the World Cup.
With just over a week to go, the boss does not know how many signings – if any – he will make.
“Last season I told you some numbers, but this season we don’t know,” Pochettino told several national newspapers ahead of his side’s final friendly of their United States tour against AC Milan.
“I don’t know if we are going to sign or not. We’re working on that. I cannot tell you if we’re going to sign one, zero or two or three or four.
“We’re working. It’s true that it’s so close, the transfer window is so close, but the club’s doing everything to help the team and add some players, more quality, and try to help us in the season to achieve what we want.”