For years, Tottenham have been linked on and off again with a potential dream move for Manchester City winger Jack Grealish, and with the player getting phased out of the City starting lineup by Pep Guardiola after the club signed young guns like Savinho and Jeremy Doku, it seems like that transfer could be a reality in 2025.
Tottenham, for their part, have a signifiant need for help on the wings. They are looking at top options on the right wing like Bryan Mbeumo and Antoine Semenyo, while they may have to prepare for life without Son Heung-min on the left wing.
Grealish can play either position but is at his best on the left, and Tottenham have already been concretely linked to the 29-year-old. Even though Grealish is heading closer to 30, he's still a few years younger than Son and has kept himself in great fitness over the years; he may be itching to play a bigger role for a club like Tottenham after dimming his own shine to help Man City win the 2022/23 treble.
Pep Guardiola doesn't value Jack Grealish these days
According to Fabrizio Romano, Grealish was officially left off the final Manchester City squad for the Club World Cup, and that all but confirms Grealish won't be a Man City player next season. There is so much prize money on the line in the Club World Cup that Man City wouldn't leave a player off unless they were actively looking to sell them and didn't want to make the Club World Cup squad registration an issue.
Nor does it sound like Guardiola thinks Grealish is important to him anymore, which is backed up by small of a role he plays for the club now. This squad move is a statement from Guardiola to other clubs around Europe - potentially even Tottenham specifically - that Grealish is for sale this summer.
Tottenham's priority on the left wing should be to seal a Mathys Tel transfer, but it's clear that Spurs won't - and shouldn't - consider that position solved with the young and developing Tel alone, especially if Son is sold to, say, Al-Hilal.
Grealish could be a big domino to fall in the Premier League transfer window, and he is a potential comeback candidate in a new environment where he'd have more freedom to be creative. The big key will be seeing if Thomas Frank is interested in resurrecting Grealisih as one of the best players in English football.