With Villa on the brink of administration under previous owner Dr Tony Xia, Daniel Levy held off on bidding for Grealish as he was trying to take advantage of the precarious financial situation at Villa Park.
Villa have been saved from their financial woes after Xia sold his majority stake in the club to billionaires Nassef Sawiris and Wes Edens.
The new duo have given their backing to manager Steve Bruce and promised to help him improve on Villa's performance last season, when they lost out in the playoff final against Fulham.
However, the new ownership does not necessarily mean that Villa are safe from Financial Fair Play (FFP) regulations, and Levy is hopeful that this situation may allow Spurs to sign Grealish on the cheap.
The Mirror claims that Grealish wants to return to the Premier League and believes that playing alongside the likes of Harry Kane and Dele Alli can boost his own international ambitions.
Grealish was born in Birmingham and, despite representing the Republic of Ireland at youth level, he has confirmed that he wants to play senior international football for England.
The 22-year-old broke into Villa's first team the season before they were relegated from the Premier League.
To some people's surprise, he has remained at Villa throughout two years in the Championship and Bruce will be determined to keep him on board for another promotion push this coming season.
Bruce has warned Tottenham that Grealish will not come cheap despite Villa's complicated financial situation.