A picture of the England international, shirtless on an open-top bus parade in the pouring rain, with arms outstretched, was one of the defining images of the aftermath of the Cityzens' greatest season in their history.
Along with the laddish antics that followed, here was a player certainly living up to his 'Jack the lad' image, but now, just three years later, that image has faded and the 30-year-old is at a career crossroads.
The form that saw Grealish play a vital part in England's run to the European Championship final in 2021 has all but deserted him, and the injury he succumbed to whilst on loan at Everton last season curtailed any chance of him making a real success of that move.
Will Grealish be in Enzo Maresca's plans?
With Enzo Maresca having now taken over from Pep Guardiola at Man City, there are serious questions to be answered over the course of the next few weeks, as Grealish plots what might be next in his career.
Though a stay at City isn't out of the question, given Maresca will know all about Grealish's way of working from his previous stint at the club as one of Pep Guardiola's assistants, it would seem unlikely at this point.
David Moyes might well try to get him back on loan at Everton, for there was a modicum of success during his initial time at the Hill Dickinson Stadium.
Or, with Grealish's reported £300,000 weekly salary arguably proving problematic for many clubs (only Virgil van Dijk and Erling Haaland earn more in the Premier League), he could well seek his future abroad.
One assist in every five games
All will soon be revealed, but in terms of his output, what would the player bring to a potential buying club, or even to City itself?
Since joining the North West giants and also taking into account last season's loan at Everton, he has made a total of 179 club appearances in all competitions, scoring 19 goals and providing 29 assists.
Even if we acknowledge that scoring isn't his forte, just one assist in roughly every five games couldn't really be classed as an elite-level showing.
Despite playing significantly fewer minutes than his City colleagues, too, he has racked up an astonishing 22 yellow cards, with only Rodri and Bernardo Silva earning more.
Creativity
With 275 chances created during his time at the Etihad Stadium, Grealish can at least point to being one of the more creative players in the squad; however, if we look at his passing, he falls way behind his teammates.
An 88.02% pass completion isn't to be overlooked, but his total of 4,823 passes made can't compare to 18,918 made by Ruben Dias, for example. Even the injury-prone Gabriel Jesus, who left the club to join Arsenal, had made 3,030 whilst at City, in the same time frame as Grealish.
A move elsewhere was therefore always on the cards, though to his credit, Grealish did up his numbers at Everton before the injury cruelly ended his 2025/26 season early.
For example, the 42 chances created could only be topped by James Garner's 59, whilst his 56.25% shot accuracy was behind only Jake O'Brien and Iliman Ndiaye.
Is Grealish still just a 'maverick'?
Three yellow cards in 22 games played for the Toffees could be improved upon, though, looking beyond that, Grealish was much more involved in Everton's play than he was when given opportunities by Guardiola prior to the loan.
Turning 31 not long after next season begins, there is a real need for Grealish to either get his head down and work harder than ever at City, to ensure Maresca has no other option than to play him, or to go elsewhere to revive what might otherwise be a fading career.
For a player who's long been considered a maverick, it'll give those who always use the term disparagingly even more ammunition to suggest there's no place at the top table in today's game for such a player.
Grealish has shown in flashes that he's about much more than that, of course, and, given the right opportunity, wherever that may be, he can still come up with the goods and be a worthwhile squad player.
Jason Pettigrove has been the features writer for Flashscore since 2025, utilising Opta data to form the basis of his articles. He has previously worked for high profile football clubs, news and media outlets, both in print and digital, and can usually be found watching FC Barcelona when time permits. You can read more of his pieces here.
