Jack Grealish: A Complicated Journey at Manchester City
Jack Grealish was supposed to be the future when he walked into the Etihad in the summer of 2021, the £100 million man who smashed British transfer records and became the Premier League’s first nine-figure signing. Boyhood hero at Aston Villa, new jewel of Manchester City, poster boy of a new era.
Three years on, his story is far more complicated.
The Treble season should have cemented everything. Grealish lifted the Champions League and paraded trophies through Manchester, but the numbers never quite matched the noise. By the end of the 2024-25 campaign, he had 17 goals from 157 City appearances – tidy, useful, but hardly the devastating output many expected from a £100m attacking midfielder.
Under Pep Guardiola, the sense grew that his edges had been smoothed a little too much. The freedom that made him irresistible at Villa often gave way to structure, control, and positional discipline. As City evolved again, Grealish quietly slipped down the pecking order.
That slide opened the door to Everton.
The loan to Goodison Park felt like a reset, a chance to rediscover the swagger that once made him the most fouled player in the league and a magnet for chaos. Early signs were exactly what he needed. He hit form quickly on Merseyside, scooped a Premier League Player of the Month award and looked like a man playing with the handbrake off.
Then his season snapped.
A stress fracture in his foot in January cut everything short. Surgery followed. So did the end of his World Cup hopes. For a player with 39 England caps, the timing could not have been worse.
The injury did not just cost him a tournament. It changed the conversation around his future. Everton, who had a £50m purchase option written into the deal, stepped back. They chose not to trigger it, instead hoping that Manchester City might soften their stance in summer negotiations. So far, there has been no agreement.
On the international stage, the picture is just as intriguing. England reached the semi-finals of FIFA’s showpiece in North America without anyone truly nailing down the left wing. The role remains open, the debate very much alive.
Lee Sharpe, the former Manchester United winger and Premier League title winner, believes Grealish is still firmly in that mix, even if competition is fierce.
“They seem to have a bit of an abundance of left-sided players,” Sharpe told GOAL, speaking in association with NetBet. “Like you say, you've got Grealish, you've got Cole Palmer that can play there, although I'm not sure either of them are really that out-and-out, winger-type, quick-to-go-by people. I think [Anthony] Gordon and [Marcus] Rashford between them had decent World Cups.
“There's two strong candidates for the left-sided players and it just depends on what sort of football and what team they're playing against.”
Sharpe still carries a small regret from that World Cup run. His mind goes back to the clash with Argentina and a tactical switch he never saw.
“I was wishing they'd brought Rashford on against Argentina and just put the ball near the corner flag for five or 10 minutes and chased after it and turned Argentina around. That didn't seem to happen.
“A Grealish or a Palmer would have probably kept the ball, but I'm not sure they've got that pace to go and threaten in behind when you need to do so. But yeah, once Jack Grealish gets himself fit and Cole Palmer keeps himself fit and gets over his little injuries that he had last year, they're phenomenal players and they're game-changing players.”
For Grealish, the next step is brutally simple.
He has to stay on the pitch.
Sharpe is clear about what the 2026-27 campaign must look like for the 28-year-old after a stop-start period at City and a cruel interruption at Everton.
“He just needs a year of staying fit and not getting injured. Every player needs that,” Sharpe said. “It's soul-destroying when you get injured and you know you've got a long rehab and you're not going to see many of the lads. You're going to miss out on everything that goes on with the lads and the season. You just want to play.
“It's so hard to be injured for anybody, mentally, physically, and then to come back from it. The rehab, getting fit again, getting back into the team again, your timing and getting your game back for match days.
“It's a horrible process, but he just needs 10, 12, 15 games now to get back up to speed and get his confidence fully flowing. I'm sure we'll see another great year from Jack Grealish.”
That confidence, when it comes, still frightens opponents. Sharpe has seen enough to know that the talent has never been in doubt.
“He's unbelievable. He's got so much ability. I remember back to the England game, I think it was the Germans we played against. He just bossed the whole game. They couldn't get the ball off him. That's the kind of player he is.
“He's so comfortable on the ball. He can run with it. He can slot a pass in. He can score a goal. He's got so much ability. He's great to watch. He plays with a smile on his face. He's great with the fans. I think he's a credit to the game and to himself.”
So Grealish stands at a familiar crossroads: too gifted to ignore, too disrupted by injuries and inconsistency to be guaranteed anything. City must decide his fate. Everton wait in the wings. England’s left flank remains a live audition.
The record fee is history now. What matters is whether he can turn the next season into something far more valuable – a stretch of football that reminds everyone why he was worth betting £100m on in the first place.
