Jack Grealish arrived at Everton this season speaking of feeling loved, yet he now finds himself out in the cold after another off-field indiscretion — one that threatens not only his career but the broader legacy of a generation of English talents long compared to Paul Gascoigne.
Jack Grealish's Everton Troubles Raise Questions Over a Lost Generation

Jack Grealish arrived at Everton this season speaking of feeling loved, yet he now finds himself out in the cold after another off-field indiscretion — one that threatens not only his career but the broader legacy of a generation of English talents long compared to Paul Gascoigne.
Grealish was excluded from the squad for Everton's Carabao Cup victory over Newcastle United following a reported breach of club discipline, and was then deemed unfit for the Premier League rematch at St James' Park days later. On neither occasion did manager David Moyes's side appear to miss the winger.
A familiar pattern at Everton
The club has yet to issue a final verdict on Grealish's reported unauthorised absence from training, but patience is wearing thin among both the board and supporters. Moyes was already navigating a threadbare squad — only 18 senior players remained available after a difficult summer window — and Grealish's latest lapse handed him an unnecessary complication.
There was always a risk of history repeating itself. During his initial loan spell at Goodison Park, Grealish spoke of feeling at home on Merseyside, so much so that he completed the bulk of his rehabilitation from a foot injury — sustained in January — at Everton's Finch Farm training ground rather than returning to Manchester City. Yet even that goodwill was tested when, as Everton fell to a late defeat at West Ham in April, photographs emerged of Grealish at a Manchester rooftop bar, surrounded by bottles and glasses.
The Gazza generation
Now 31, Grealish is in danger of completing an unfortunate trio alongside Dele Alli and Raheem Sterling — three talents, born within 16 months of one another, who were once touted as successors to Gascoigne's throne and whose careers have each unravelled in painful fashion.
The parallels run deep. Upon returning to Everton this summer, Grealish revealed he had chosen the No.18 shirt partly in tribute to Gascoigne, who wore it during his own brief spell at the club. Sterling has named Gascoigne as his all-time favourite England player. Even Dele, who also sought a fresh start at Everton, once recreated Gascoigne's notorious dentist's chair celebration during a training session at Euro 2016. Each was individually labelled the new Gazza at some point, and each has, to varying degrees, embodied the self-destructive tendencies that shadowed Gascoigne's later years.
Gascoigne himself told FourFourTwo last year that Grealish was the closest embodiment of him among the current generation of players — no small statement from English football's most compelling flawed genius.
Where the others stand
Dele is now 14 months into what amounts to an unofficial retirement, reduced to calling former teammates live on Twitch in an attempt to remain relevant. A widely-shared clip of an awkward exchange with Harry Kane — just weeks before Kane claimed the Ballon d'Or — lasted barely 60 seconds. Dele's continental ambitions amounted to brief spells at Besiktas and Como, the latter ending with a single appearance before his release partway through an 18-month contract.
Sterling's situation is no less sobering. His three-month stint at Feyenoord was terminated last season, leaving him without a club. He now faces the prospect of a custodial sentence after pleading guilty to dangerous driving while inhaling nitrous oxide, having crashed his Lamborghini on the A327 in May.
A precedent for redemption
Grealish's situation is not necessarily irreversible. Ross Barkley, another mid-90s talent who carried the Gascoigne comparison and endured his own off-field difficulties, managed to rebuild his reputation through spells at Nice and Luton Town before earning a role under Unai Emery at Aston Villa. Persistent injuries limited what Barkley ultimately achieved, but the arc of recovery is there.
Grealish's performances during his first loan spell at Everton showed his technical quality remains intact. His role in Manchester City's treble-winning campaign in 2023 hinted at a player who, at his best, was capable of competing at the game's highest level. Whether he can impose the same discipline on himself off the pitch that he demonstrates on it will determine whether this generation's story ends in redemption or in the shadow of Gascoigne's cautionary tale.

