Reaction online and elsewhere from Everton fans to the news of Jack Grealish joining the club on a season-long loan has been resoundingly positive, ranging from thumbs-up approval to outright delight.
There are several reasons for this, namely Grealish’s status as an immensely talented, high-end footballer — the sort of which has not graced the Everton dressing room since James Rodriguez’s Merseyside sojourn.
There’s also the 29-year-old’s enduring status as an authentic no-filter cult hero, the type of figure the modern superclub game tends to deny fans. This reputation and popularity has survived a British-record transfer and very mixed returns over the course of four seasons at Manchester City.
‘Jack the lad’ is still a warm, affable everyman who most neutrals are rooting for as he begins a new chapter.
But, while this is an exciting time for Everton as they embark upon life at Hill Dickinson Stadium, there’s the simple fact that Grealish has swapped life as one of the top earners in Pep Guardiola’s squad of superstars for a club more familiar with the realities at the wrong end of the table in recent years.
So, how has it come to this?
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What went wrong for Jack Grealish at Man City?
Put simply, Grealish did not spend enough time on the pitch over the past two seasons. More importantly, Pep Guardiola no longer felt he could trust the player to be reliably fit to do the job he knew he was capable of.
The shorthand breakdown of Grealish’s City career checks out well enough — typical first season of an attacking player acclimatising to Guardiola’s demands; second-season treble star; seasons three and four, generally awful — but there’s a little more to it than that.
Take City’s UEFA Champions League knockout-playoff clash with familiar foes Real Madrid last season. Grealish starred as City hammered Carlo Ancelotti’s side 5-1 on aggregate in the 2023 semifinals and started both legs of a 2024 quarterfinal that ended in a penalty shootout loss.
Despite not starting a Premier League match in 2025 up until that point, Guardiola named Grealish in his XI to take on Madrid on February 19. Stationed in his familiar left-wing position, he played very well and his superb chipped pass led to Erling Haaland’s opening goal.
Then, in the 30th minute, Grealish went off injured. City lost the match 3-2 and were well beaten at the Santiago Bernabeu. It felt like a breaking point for Guardiola’s trust in the player, who only started one more Premier League match across the rest of the season.
Another example of what could have been was the opening 20 minutes of City’s Champions League last-16 clash at Copenhagen in 2023/24. Grealish made his first start in a month and lined up in an attacking midfield four alongside Phil Foden, Bernardo Silva and Kevin De Bruyne, in front of Rodri and behind Haaland.
City produced the sort of whirring, frictionlessly brilliant football their 2023/24 often lacked during the first 20 minutes. Grealish was fantastic. Then he got injured, as he did two weeks later at Luton Town in the FA Cup, where Guardiola seemingly questioned his winger’s application when invited to provide reassuring words afterwards.
“He played lots of minutes last season and this [season] less in the beginning — it’s the way he has performed. That’s the difference,” the City manager said. “I said from day one: ‘We need him, he has a special quality for our team.’ It depends on him. Hopefully, he can do a good last three months.”
Grealish did not have a good three months and missed out on England’s Euro 2024 squad. He played a full part in City’s preseason schedule and was raring to go for 2024/25 before injury struck on the eve of the Community Shield. Further setbacks followed, along with allusions to mental health struggles. In January, Guardiola lamented how he had “fought” for Grealish and there was sadness on both sides that the relationship was at an end, in a way it probably wouldn’t have been if the former Aston Villa favourite simply wasn’t good enough.
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Is Jack Grealish Pep Guardiola’s worst Man City signing?
No, that dubious distinction belongs to the deeply unsavoury period that was Benjamin Mendy’s six-year contract at the Etihad Stadium. The France defender endured a succession of injuries and disciplinary problems before not playing for the final two years of his deal. This was due to a club suspension and Mendy being remanded in custody over multiple rape and sexual assault charges, of which he was later found not guilty.
Grealish’s England teammate Kalvin Phillips is also worthy of a mention, having looked an ideal foil for Rodri as a £42m signing from Leeds. The Marcelo Bielsa favourite never came close to the required standard.
Similarly, Claudio Bravo was haphazardly inept during Guardiola’s first season in charge in 2016/17. Forcing crowd favourite and modern club great Joe Hart out to make way for the Chile international was the factor to tip that transfer into shambles.
The thing with Grealish is that, when he was on the pitch as a key component in the greatest achievement in City’s history, he was absolutely and completely good enough, unlike the men above. His City downfall is a little more nuanced.
Will Everton get the Aston Villa Jack Grealish back?
A lot of the popular conversation around Grealish is that Everton will get the bold, freewheeling risk-taker of his Aston Villa days. A man cruelly shackled by the tyrannical Pep Guardiola will be allowed to bloom by Renaissance man David Moyes. Football discourse in 2025 is quite the thing.
Villa Grealish has understandably gained a sort of mythic quality. The Birmingham native was the hero who made the journey from the terraces to the field at his boyhood club. As his stock rose, England honours followed and City emerged from the pack to make him a superstar signing. He was an undeniably thrilling player to watch.
Under Guardiola at City, there were different demands — demands that he managed to carry out by giving the team shape and structure, and cherishing possession. Instead of being the main man, he had to share space with the likes of Foden, De Bruyne and Ilkay Gundogan.
However, the notion that Grealish was simply told to hug the touchline, shuffle forward, pass the ball backwards or win a foul is off the mark. If wingers were told to be “boring” by Guardiola, how exactly do we explain the performances of Franck Ribery, Arjen Robben, Raheem Sterling, Leroy Sane, Riyad Mahrez and Jeremy Doku under his management?
The lack of output in terms of goals and assists is, to a large extent, on Grealish. But then, he’s never been a big numbers guy. His 10 goals in all competitions for Villa in 2019/20 remains the only time in his career he has hit double figures in a campaign. His 11 assists during City’s treble season are his best on that metric, having set up 10 goals in his final year at Villa.
Even at this stage, more than a decade on from his Premier League debut and all the adoration that’s followed, so much about Grealish remains up for grabs, down to your perception and what you like. In a World Cup year, he must now deal in the cold, hard and indisputable facts of an impressive season at Everton to get his career back on track.
