Former Tottenham manager believes that his former club could end up regretting having not signed Aston Villa midfielder Jack Grealish as he could have gone on to be a star for the team.
The attacking midfielder was one of the players whom Mauricio Pochettino had hoped to sign during the summer transfer window.
During the early parts of the transfer window, it looked as if a deal was likely to go ahead as Villa were struggling financially.
However, their financial problems were solved after the club had been bought by new investors and this led to them hardening their stance on a possible sale for Grealish.
Spurs reportedly made a £25 million bid for Grealish on Wednesday but were informed by Villa that they would not sell for any price.
Grealish is regarded as one of the best up and coming attacking players in English football and it will not be surprising if Tottenham make another move in the near future.
For now however, the player will focus his attention onto helping Villa launch a possible promotion bid this season.
The Villains narrowly missed out on promotion to the Premier League last season as they ended up losing 1-0 to Fulham during the playoff final.
Sherwood who worked with Grealish while he was with Villa 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.”
“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.”