Jack Grealish, the £100m winger who went back to Everton to feel wanted again

Jack Grealish

Photo: Hameltion / CC BY-SA 4.0, via Wikimedia Commons

Born	September 10, 1995 Birmingham
Occupation	Footballer
Honours	Champions League 2022-23 · Premier League ×3 · FA Cup 2022-23 · Super Cup 2023 · Euro final 2020 · Premier League ×3
Individual awards	UEFA Champions League · Premier League · FA Cup · UEFA Super Cup · UEFA Euro 2020 finalist

Twice in thirteen months, Jack Grealish has packed a bag at the club that paid a nine-figure fee for him and driven to Merseyside, where nobody asks him to be anything other than himself. He has won everything Manchester City could put in his hands, and yet the sentence he reached for when he returned to Everton this September was about feeling loved, by a manager and by a crowd. That is the real subject of his career: a footballer built for devotion who spent four seasons inside the most precise machine in world football and came out with the medals but without the certainty that he mattered.

The devotion started in Solihull, a few miles from Villa Park. Grealish was born in Birmingham and grew up a Villa supporter in an Irish Catholic household: grandparents from County Dublin, from Gort in County Galway and from Sneem in County Kerry, Catholic schools in Solihull, and four years of Gaelic football with John Mitchel’s in the Warwickshire GAA between the ages of ten and fourteen. His family carries its own losses. His younger brother Keelan died of sudden infant death syndrome at nine months old, when Jack was four. His sister Hollie has cerebral palsy, and he has called her his best friend. There is even a thread back to the club he adored: his great-great-grandfather, Billy Garraty, won the FA Cup with Aston Villa in the Edwardian era.

Born on 10 September 1995, he joined Villa’s academy at six, after a spell at Highgate United, and sat on the bench for a Premier League match against Chelsea at sixteen. A youth loan at Notts County in 2013-14 gave him 39 games of League One football and five goals, including a run past three defenders against Gillingham that announced the style: low centre of gravity, the ball glued close, defenders drawn in and then left behind. Back at Villa he played the whole of the 2015 FA Cup final at nineteen, lost 4-0 to Arsenal, weeks after setting up Fabian Delph’s winner in the semi-final against Liverpool.

The next four years tested whether the talent would survive the person carrying it. Photographs of him apparently inhaling nitrous oxide drew a public warning from Tim Sherwood; Rémi Garde sent him to train with the under-21s after a night out in the North West. The 2015-16 season ended in relegation, and Grealish finished it with a record nobody wants: sixteen appearances, sixteen defeats. In July 2017 an elbow from Tom Cleverley in a pre-season friendly ruptured his kidney, an injury he later described as life-threatening. Then, in March 2019, he was handed the armband. Villa won ten league games in a row, he was punched from behind by a pitch invader at Birmingham City and scored the winner in the same match, and a play-off final against Derby County took the club back up.

His 2019-20 season is the one Villa supporters still quote. Grealish was fouled 167 times, the most ever suffered by a player in a single Premier League campaign, scored ten goals in all competitions and struck on the final day against West Ham to keep a side built for relegation in the division. The following October he scored twice and set up three more in a 7-2 win over Liverpool, the reigning champions. By then the child-sized shin pads, the socks rolled to the ankle and the comparisons with Paul Gascoigne had made him one of the most recognisable footballers in England outside the traditional elite.

On 5 August 2021 Manchester City signed him for a fee reported at £100 million, at the time the most expensive transfer of an English player, on a six-year contract running to June 2027. He took the number 10 vacated by Sergio Agüero. The first season brought a Premier League title and an admission that adapting to Pep Guardiola’s football was “much more difficult” than he had imagined. Kevin De Bruyne argued that English players were easy targets; İlkay Gündoğan said Grealish was “so misunderstood” by parts of the media.

The second season answered the doubters, briefly and completely. In the treble-winning 2022-23 campaign Grealish became the balancing piece on City’s left: by the first leg of the Champions League semi-final he had created 35 chances in that season’s competition, a record for an English player, and in the 4-0 return against Real Madrid The Guardian called him “scintillating”. He played the entire Champions League final against Inter in Istanbul, won the FA Cup and a second Premier League title, and the BBC described him as almost undroppable for the big games. The celebrations that followed, filmed from plane steps to the open-top bus, confirmed the other half of his reputation. The following season added the UEFA Super Cup, where he scored in the shoot-out against Sevilla, the Club World Cup and a third league title.

The critical reading of his City years is less about talent than about fit. Guardiola’s wide players are asked to hold width and release the ball early; Grealish’s gift is to receive, slow the game, draw fouls and wait for the pass that breaks a line. In a system that prizes control, that pause looked like security in 2023 and like hesitation afterwards. Across all competitions he made 159 appearances for City and scored 17 goals, twelve of them in the Premier League. In 2024-25 he managed a single league goal and was left out of the squad for the 2025 Club World Cup. Guardiola praised his professionalism in public; the team sheets said something colder. The Gascoigne comparisons, meant as affection, also did him no favours, framing a disciplined, hard-working winger as a hedonist whose best days were always about to slip away.

England told a similar story at international level. Grealish represented the Republic of Ireland up to under-21 level before choosing England in September 2015, won the Toulon Tournament with the under-21s and made his senior debut against Denmark in September 2020. At Euro 2020 he came off the bench against Germany and was involved in both goals of a 2-0 win on the way to the final. At the 2022 World Cup he scored against Iran and waved his arms in the celebration a young City fan with cerebral palsy, Finlay, had asked him for. He was cut from the final Euro 2024 squad, and his 39th cap, with four goals, came in October 2024.

Everton offered what City could not: a team built around him. Loaned out in August 2025, he set up both goals on his first start against Brighton, the first competitive assist at Hill Dickinson Stadium, and was named Premier League Player of the Month for August, the first such award of his career. His stoppage-time winner against Crystal Palace ended their nineteen-match unbeaten run, and another winner followed against Bournemouth in December. Then, in a 1-0 win at Villa Park on 18 January 2026, he suffered a stress fracture of the foot. Surgery ended his season with two goals and six assists from twenty league games, and ended any chance of going to the 2026 World Cup.

The summer offered one more look at the City version. He played the second half of a 3-0 Community Shield defeat to Arsenal and came on late in the Premier League opener against Bournemouth. On 1 September 2026 he went back to Everton on a season-long loan, back under David Moyes, speaking openly about how much the trust of manager and supporters meant to him. His first appearance of the new campaign came off the bench against Manchester United, in place of Brennan Johnson.

Away from football, Grealish has been with Sasha Attwood since the two met at school at sixteen; their daughter, Mila Rose, was born on 27 September 2024. His public record also includes a nine-month driving ban and a fine of £82,499 for two counts of careless driving in 2020, a club fine at Villa for breaching lockdown rules, and a burglary at his Cheshire home in December 2023. He has said that, had football not worked out, he would have liked to be a club promoter in Ibiza or Tenerife.

What remains is a season with a fixed horizon. His City contract expires in June 2027, which makes this Everton year the last one in which the £100 million question can be asked on someone else’s terms. Emiliano Martínez once called him the most talented player he had ever seen. At 31, fit again and wanted again, Grealish has nine months to show whether that talent was ever the problem, or simply the club.

Tags: sports, athletes, footballers, Premier League, Manchester City, pep guardiola, Aston Villa, Everton, David Moyes, Jack Grealish