Jack Grealish’s demise is the beginning of the end for the ‘Gazza generation’
Deep down, Jack Grealish will know that his fate extends beyond Everton’s season.
English football’s first £100m player has won multiple Premier League titles and a Champions League yet still faces a fight to stave off the death knell to an increasingly lost generation as much as his own elite-level career.
Grealish again finds himself out in the cold after a ‘breach of club discipline’ in the run-up to Everton’s Carabao Cup win over Newcastle and was subsequently deemed unfit for the league rematch at St James’ Park on Monday night. On both occasions, David Moyes’s side were hardly poorer without the winger’s presence.
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Jack Grealish’s Everton travails follow a familiar pattern

The Toffees are yet to decide on a definitive course of action over Grealish’s reported unauthorised absence from training, but patience is now in increasingly short supply from the club and its supporters alike. At a time when Moyes is dealing with crippling squad dearth – just 18 senior players were left after a disastrous summer window – the England international’s latest misdemeanour threw him another needless curveball.
There was always a risk that Grealish’s propensity to hit the headlines for the wrong reasons would again rear its head on Merseyside, where he claimed that feeling ‘loved’ in his initial loan spell was a driving factor in embarking on a second. Such was a fondness for his current surroundings that he undertook the bulk of his rehabilitation from a season-ending foot injury sustained in January at their Finch Farm training ground instead of returning to parent club Manchester City.

But even then, indiscretion was still lurking round the corner. When Everton slipped to a late April defeat at relegation candidates West Ham, Grealish was being snapped slumped against the arm of a chair in a Manchester rooftop bar surrounded by bottles and glasses. Now 31, he is in danger of completing an unholy trinity that was once touted for greatness as successors to Paul Gascoigne’s throne but allowed their careers to crash and burn.
Just 16 months separate the respective birth dates of the Birmingham-born talent, Dele Alli and Raheem Sterling. All three were alive when English football’s flawed genius enjoyed one last hurrah at Euro 96 but none will have any memories of it. That has still done little to stop their affection for ‘Gazzamania’ running deep.
Upon his return to Everton this summer, Grealish revealed he was partly inspired to take the No.18 shirt worn by Gascoigne during a forgettable and fleeting spell in the blue half of Merseyside while Sterling also cited the man that personified the 1990 World Cup as his all-time favourite Three Lions player. Even Dele, who himself previously sought redemption at Everton, made an embarrassing attempt at recreating the infamous ‘dentist’s chair’ celebration during a training session at Euro 2016.
They also appeared destined to follow in his footsteps by earning moves to high-profile leagues overseas with Real Madrid heavily touted as a future destination for each player. Beyond personal homages, Gascoigne has become intertwined with the trio as a quickfire buzzword for their respective rises to prominence. Individual billings as the ‘new Gazza’ also proved to be a self-fulfilling prophecy for a penchant for self-destruction mirroring the downfall of the former Rangers and Lazio playmaker. Dele is now 14 months into unofficial retirement and resorting to calling up former teammates live on Twitch streams in a desperate ploy to stay in the public consciousness. An awkward attempted catch-up with Harry Kane, just weeks before his old Tottenham sparring partner claimed the Ballon d’Or, lasted barely 60 seconds.
The depth of Dele’s continental ambitions was short-lived spells with Besiktas and Como, making a solitary appearance for the latter before being released barely midway through an 18-month contract. Free agent Sterling fared far worse with a three-month spell at Feyenoord which was terminated last season. Grealish’s former City teammate and fellow Euro 2020 standout faces the real prospect of ending this month behind bars as well as without a club after pleading guilty to dangerous driving while inhaling nitrous oxide and crashing his Lamborghini on the A327 in May.

Without sufficient intervention on his own part, Grealish may soon follow his former contemporaries in falling by the footballing wayside. More than most, he has been the poster boy for Gascoigne’s heirs, as the man himself confirmed to FourFourTwo last year by singling out the former Aston Villa graduate as his closest embodiment in the current crop of players. His exploits in City’s 2023 treble-winning campaign hinted that England’s first Ballon d’Or winner since Michael Owen was closer than Kane’s recent triumph but never came to pass. What happens next will be era-defining.
Grealish is still capable of technical excellency, as demonstrated in a truncated first loan spell with Everton, if he can stave off personal indiscipline issues. He would not be the first homegrown talent to do so. Ross Barkley, another ex-teammate born in the mid-90s, was also festooned with the Gascoigne moniker yet managed to overcome his own off-field issues to earn a second chance at Villa. Persistent injuries prevented the playmaker from scaling even a fraction of the heights he was originally tipped to reach but used stints at Nice and Luton Town to rebuild his reputation and earn a bit-part role with Unai Emery’s side.
By personal admission, Grealish has been his own worst enemy when it comes to a sense of timing off the pitch which is at odds with an often impeccable nature on it. Unless he can conquer those social demons which ultimately brought down his idol as well as those in the same talent pool, the epitaph of the ‘Gazza generation’ will be one of frustratingly unfulfilled potential.





