If you were to ask Jack Grealish to choose the highlight of his career so far, he wouldn’t be short of options.
Manchester City won the Champions League in 2023, part of a historic treble as well as City’s first European Cup win. Maybe he’d pick that. It would be difficult to argue.
In October 2021, Grealish scored his first goal for England. His second, 13 months later, was at the 2022 World Cup. Maybe he’d pick that. He’s fiercely proud and protective of his international career.
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As is so often the case with Grealish, it might not be as simple as all that. Before a record £100 million transfer to Man City in 2021 he was the captain of Aston Villa, the club he’s supported all his life and where his exploits on the pitch represented another kind of success.
Grealish was one of those players most clubs get every now and again, precocious youth-level talents who get supporters all frothy with excitement before they even join the first team.
He fulfilled all that promise. What’s more, he did it at a difficult time for the club and, along with fellow supporter and manager Dean Smith, dragged Villa kicking and screaming back into the top division.
If you’d asked Grealish four years ago to choose the highlight of his career so far, the answer would have been easy.
In May 2019, Grealish captained Villa in the Championship play-off final at Wembley. They beat Derby County 2-1 to win promotion to the Premier League and Grealish, battered boots and all, was the man of the moment.
That the play-off winners are presented with a trophy isn’t to everyone’s taste. Villa finished fifth in the second division that season, which doesn’t really warrant silverware.
But watching Grealish hold that trophy aloft to end Villa’s three-year stay in the Championship meant the world to the supporters who followed their team into English football’s most lucrative match a year after the disappointment of defeat.
It was the end of something special and the start of an unknown, exciting future. Grealish was the player who linked the two.
Maybe, just maybe, he’d pick that.
It’s usually overlooked how important Grealish was to Villa culturally as well as on the pitch. The wider football public has come to understand his qualities as a player primarily through the prism of Man City’s tactical approach under Pep Guardiola but the Villa version wasn’t just some raw talent waiting to be harnessed.
Grealish at Villa was a different animal. The team was geared around him to such an extent that it became difficult for subsequent managers to unravel the reliance upon him after his £100 million move to the Etihad.
Everyone knows that. What’s not so commonly recognised is that Grealish was so good at Villa, so unique, that there was simply no other way to manage him or a team with him in it.
As Grealish led Villa to Premier League safety and a vastly improved season in 2020/21, including a display against Liverpool that’s ranked number 99 in FourFourTwo‘s list of the greatest individual performance of all time, his price tag increased and Villa supporters were including him in serious conversations about their best-ever players.
Paul McGrath. Brian Little. Gordon Cowans. Jack Grealish. That’s a degree of admiration that’s impossible to shake.
Villa’s Grealish was brilliant when unshackled, unconstrained, but trophyless and full of ambition. He moved to City when his colossal release clause was activated and his medal collection justifies his decision completely.
But the trophies and titles are just part of the story. Grealish and Guardiola seem to have been at crossed purposes for much of the 29-year-old’s time at Man City, mutual admiration palpable but not always thick enough to mask the occasional frustration.
There was a feeling among Villa supporters that their skipper wasn’t really the player Guardiola needed or wanted him to be. He can be, and he has been, but when he is that player, he’s not the full Grealish.
It’s to his credit that he’s evolved and adapted to be a capable player at the very highest level but the supporters who watched him at his best in a Villa shirt now see a player limited by the job rather than twisting and shaping the job around his style and extraordinary ability.
Grealish was wild. He carried the ball better than anyone he came up against at Villa, pace and power in perfect harmony. He went past players like they weren’t there and protected the ball any which way when there was nowhere to go. His touch was immaculate. His goals were sensational.
He might never be that Grealish again and only the man himself can weigh up the pros and cons of swapping that delicious swagger for tangible success.
Either way, his days at Man City are numbered. Guardiola’s patience seems to be wearing thin and he’s falling out of favour.
The end product he finally unlocked at Villa has gone and he’s started just 16 times in the Premier League since the start of last season.
With Guardiola and City seeking to use the January transfer window to resurrect their season, Grealish will be allowed to leave if the opportunity arises. His contract runs to the summer of 2027, so he’s now in prime selling territory. From City’s point of view, cutting loose an unwanted player with some value left in his contract is now the best-case scenario.
Grealish has one more big move left in him. His wage demands will limit his options but, for supporters and football enthusiasts away from City, the purest hope is that the former Villa man finds a club where he can recapture a little of what made him special enough to cost £100m in the first place.