Levy still believes the deal can be done, according to James Nursey of the Daily Mirror, even though Villa are now backed by Nassef Sawiris and Wes Edens. The billionaires purchased a majority stake in the club from Dr Tony Xia in July, while Levy had been holding off on making a bid while Villa were in financial turmoil.
Nursey said Levy "was trying to exploit Villa's cash woes under Dr Tony Xia, which left the Championship club on the brink of administration." Talks between Spurs and Villa over the potential transfer only got under way recently.
It may not be as easy as Levy thinks to get Grealish for £20 million now Villa are under no pressure to sell. Football.London's Alasdair Gold reported no deal will be concluded before Spurs complete their participation in the 2018 International Champions Cup in the U.S. at the end of July.
Gold also noted how Villa's new backers are likely to want more than £30 million for the squad's creative talisman.
Villa would be wise to push for maximum value before considering selling one of the best players in the squad. The 22-year-old is coming off a season wherein he produced three goals and six assists to help Villa reach the Championship play-off final.
As to where he would fit in at Tottenham, Nursey pointed out how Spurs manager Mauricio Pochettino wants Grealish to vie for playing time with Dele Alli in support of star striker Harry Kane.
Whether Grealish would accept a squad role, even if it guaranteed moving up a division, is another matter. Yet there's no doubt he would be an asset to Pochettino's squad should he make the move to north London.
He's technically gifted, with the vision and skill to produce some magic in the final third. Grealish is a natural fit for the stylish, possession-based brand of football Spurs can play.
Aside from Alli, Pochettino can also call on the versatile duo of Lucas Moura and Erik Lamela for inspiration between the midfield and forward lines.
However, Tottenham's protracted pursuit of Grealish appears no closer to ending. Despite Levy's confidence, a club with Premier League aspirations will surely continue to drive a hard bargain for such a talented young player.