What Tottenham and Everton legends have said about Grealish ahead of Man City exit
Jack Grealish’s impending departure from Man City has multiple Premier League clubs on high alert.
The 29-year-old struggled to make an impact during a difficult 2024/25 campaign for the Citizens, making just seven Premier League starts, notching three goals and five assists across all competitions.
Supporters assumed Grealish had fallen out with Pep Guardiola due to his limited minutes, but the manager has continued to speak positively about his winger to the media.
Everton and Tottenham are two of the clubs keeping tabs on the situation, with Football Insider understanding that David Moyes will back himself to rejuvenate the Man City outcast.
However, Spurs could now jump ahead of the queue following James Maddison‘s almighty injury blow in North London, given that he could be out for most of the 2025/26 campaign after ACL surgery.
With both interested in the player’s services, Football Insider has taken a look at what legends of each club have previously said about him.
Tottenham legends
Harry Redknapp
Speaking back in 2018 [Birmingham Live], while the winger was still at Aston Villa, Redknapp said: “I looked at Villa and thought what a great young player Grealish is. He’s a magnificent young talent.
“No disrespect to Aston Villa, if they manage to get up there, great, but he really needs to be playing in the Premier League. Could he play for Spurs, though? Definitely.”
Coming from a distinguished figure who managed Spurs for a total of four years, the 78-year-old was clearly ahead of the times when discussing Grealish’s potential destination.
Harry Kane
Speaking on The Overlap in 2021, Spurs’ greatest-ever goalscorer said: “I love Jack, just love Jack as a player. Fantastic. From when he came in [to the England squad], we just had a real connection.
“He sees the game a lot how I see it… Always looking forward, always wrapping balls in, trusting your teammates. He’s a real player and one who’s going to be very special for the future.”
Robbie Keane
Keane knows a thing or two about leading the line for the Lilywhites, netting over a century of goals during his time in North London, and supporters will absolutely listen to his thoughts on the transfer.
Speaking via Betway recently, the former Republic of Ireland international said: “I love Jack. I think he’s a wonderful football player, and he’s a real Tottenham player with the way he plays and moves on the pitch.
“I really think that he could fit into the Tottenham team, whether he plays on the left, as a high No.8 or as a No.10. I’d definitely be hoping for that move to happen.”
Everton legends
Alan Stubbs
Speaking to Liverpool Echo (12 June), Stubbs said: “If a deal is going to happen, I think it will be one where Everton pay X and Manchester City pay Y.
“Listen, I’d love to see Jack Grealish at Everton. I think he’s the quality that we’re looking for. If you look at him in a No.10 role, what he can bring compared to what we’ve already got is a significant upgrade.
“I think Jack Grealish needs loving again. I think he needs to go to a club where the fans are going to adore him, and that would certainly be the case at Everton.”
Peter Reid
Speaking to The Grumpy Old Men of Football Show, Reid said: “I think the kid’s got ability. The trophies he’s won at Man City, you can’t argue with it.
“But if he went to Everton, I think he’d enjoy playing for Everton. I think the Evertonians would like him.”
Legends on both sides of the fence have glowing reports of the decorated winger, who continues to languish on the bench at the Etihad Stadium, and it remains to be seen who will win the race this summer.