According to Sky Sports, Tottenham wanted to sign Grealish from Villa in the summer transfer window.
The Premier League club reportedly made an offer of £25 million for the 22-year-old on Wednesday, but Championship side Villa are claimed to have stated that the youngster was not for sale at any price.
Former Tottenham and Villa manager Sherwood worked with Grealish at the Villans, and he has stated that the 22-year-old - who can operate as a winger or as an attacking midfielder - would have been a superstar at Spurs.
Sherwood told Sky Sports: “They wanted Jack. There is no doubt he would have improved Tottenham, not as a starting xi, but over a period of time, Jack Grealish would have been a superstar at that football club.”
The former Villa and Spurs manager added: “If he would have gone to Tottenham, he would have played this season.
“It would have been enough games, and in the future, he would be a superstar at that club and an England international.”
Going back in January?
Grealish is a hugely talented and promising young attacking player, and one suspects that Tottenham could go back for the Villa star in the January transfer window.
While it is hard to see Villa sell such a key player in the middle of the season, it would not be a bad idea for Tottenham to make an offer for him in January.