How beloved Aston Villa skipper Jack Grealish became a problem with no solution
The former Villa captain put himself in a tricky position and there's no easy way out
Aston Villa’s relationship with the new Wembley Stadium hasn’t been a happy one. For a club that played under the old twin towers less frequently than their historical success might suggest, they’ve been beaten every which way in the rebuilt home of English football.
Villa have played at Wembley eight times since it reopened and stunk the place out on six occasions, each with a different seething stench. They’ve lost FA Cup semi-finals and an FA Cup final. They’ve lost League Cup finals. They’ve lost in a play-off final. You name it, they’ve buggered it up.
Their two Wembley wins were in 2015 and 2019. The first was an FA Cup semi-final on the way down, the second a Championship play-off final on the way back up. They were oases of joy in the North London desert and they marked the beginning and end of the coming of age of Jack Grealish.
Only Villa supporters will really understand how good Grealish was when he was at his best and how exciting it was to watch him developing into one of the club’s greatest ever players.
There was Brian Little. Then there was Gordon Cowans. Then there was Jack Grealish. That’s how good he became in a Villa shirt.
England supporters got a glimpse. Notts County supporters saw the green shoots. Manchester City fans have seen flashes. Villa got the whole, glorious eyeful, from scrawny little Brummie lad to the calf colossus.
It’s important not to pretend Grealish doesn’t have his flaws and foibles. In truth, they’re all wrapped up in his current predicament: all dressed up in money and titles and nowhere to go.
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The first draft of the 2015 FA Cup final belonged to Steven Gerrard, the Liverpool midfielder who was about to leave the club and would later make a living attempting to manage Villa.
Christian Benteke and Fabian Delph tore up the script by winning the semi-final and nobody knows what happened on Gerrard’s birthday.
In that semi-final against the Reds, Grealish pulled in a ball as it dropped out of the Wembley sky. Right up against the touchline, he killed it and moved it on under pressure. It was world class. He was 19 years old.
A legend without a legacy
Grealish had a reputation by then but it was in the Championship that he really grew up. Less than a year after a pair of Wembley visits that couldn’t have been more different, Villa finally achieved the relegation they’d been flirting with for years.
The second tier didn’t toughen him up, exactly, but Grealish’s progress was supercharged by the expectation placed upon him as the most talented player at a struggling club in a brutal division. Villa needed Grealish to deliver on his potential consistently and often, and he did.
He should have played for England months before Villa were promoted and they might still be in the Championship or worse if his freakish quality hadn’t been available to Dean Smith – another Villa supporter – when he was appointed as manager in October 2018.
Wembley again. In May 2019, Villa swaggered into their second consecutive Championship play-off final full of steely determination that it would not be a similar timid failure to the first.
Anwar El-Ghazi and John McGinn scored the goals. Tyrone Mings got the plaudits. Grealish was the architect and the embodiment of his club. Even in a team that became legends, the captain was king.
He took his form into the Premier League, returning a man whence he’d left as a boy. He bossed games, now. He scored goals. He dragged his team to points all by his damned self sometimes and that was sorely needed in a relegation battle that could easily have taken them back down.
Grealish wouldn’t have gone with them.
A question without an answer
There really wasn’t a worse jump up the table Grealish could have chosen but Manchester City threw £100m at Villa and he made his choice.
It wasn’t without its plus points for an ambitious player. He wanted to nail down his England place – that might not have necessitated a move. He wanted to win trophies – that certainly did. Players at the highest level seem to want to work under Pep Guardiola and it turned out that was the delicious, juicy, poisoned apple.
Grealish’s transfer to City was utterly normal on the surface but back-to-front in reality.
He was a great player who needed to become good, a stupendous individual talent who always seemed likely to struggle to combine the need to operate in a system with his ability to play in the unique way that earned him Guardiola’s attention in the first place.
He traded maverick freedom for silverware and success. Only he can know whether that was worth it. In a short career, he’d probably say it was.
The groove, the glide, the greatness, have gone. Guardiola might have picked the wrong player for what he needed, though he’d presumably argue that it was a balance of brilliance and discipline that he expected. Grealish is culpable too. One’s mojo is one’s own responsibility.
When City signed Grealish, it might have ripped Aston Villa apart. They were abysmal under Gerrard and were fortunate to alight upon Unai Emery at the exact moment he felt a return to the Premier League was right for his career.
The player has benefited directly in some ways and lost his way a little bit in others. What he added for City is questionable. All that fuss, all the frustration on the part of Villa supporters, and I’m not really sure why they even bothered. It was a stinking fit. It was always going to be.
A problem without a solution
And so we arrive in the summer of 2025. Manchester City are fluffing Gianni Infantino’s ego at the Gianni Infantino Club World Cup and Grealish was omitted from their squad many weeks after the press were first briefed to that effect. Guardiola washed his hands of him, and, at 29, he’s finding it difficult to justify his wages elsewhere.
Grealish’s next move is a career-defining conundrum. Premier League clubs have apparently kicked the tyres. Napoli are keen but won’t be forking out City wages for a player on the doorstep of 30.
Where will he go? Will it need to be a loan? Who’s going to pay him what he wants?
Think back to those last Villa performances and it’s ridiculous that he’s won three Premier League titles and the Champions League since then and still ended up where he is right now.
There’s no easy answer but finding the right one could free up a fabulous finale for a footballer unlike any other.
Every club sniffing around him will be asking themselves whether they truly believe he can recapture what he was at Villa. He shouldn’t be in that position and the most obvious door for him to knock might be locked.
A return to Villa has been mooted often already this summer. The debate over whether he’s even good enough for them now has quieted and the biggest question marks – at least for those of us who’ve given in to our affection for the kid once more – relate to tactical and financial viability.
If those questions can be resolved, I wouldn’t be able to argue against Villa bringing Grealish home. I’m taking a rare step into the realm of the romantic because no part of my brain has ever accepted that Grealish isn’t a Villa player.
But what actually matters is that he gets out from under Guardiola and, somehow, rekindles the unshackled artistry that made him what he was.
If that’s somewhere other than Villa, so be it. If it’s a choice between sandpapered City Grealish at Villa and unorthodox genius Grealish somewhere else, go forth.
Someday, some way, somewhere, I want to see the real Grealish playing football again. I want that for him, too.
For all the anger he left behind and all the reasons Guardiola must have privately to have decided to move on, he seems like a decent young man who loves the Villa. Maybe home was the solution all along.
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