When Jack Grealish completed his record-breaking £100 million transfer from Aston Villa to Manchester City in the summer of 2021, the pressure was immense as the fee warranted it.
Everyone really wondered whether the spicy dribbling, free reigns star from Villa Park could adapt to the structured, tactical demands of Pep Guardiola’s relentless City machine.
Fast forward a few seasons, and it’s clear, Jack Grealish has been a success at Manchester City.
At Villa, he was the talisman, afforded the freedom to roam and create. At City, however, freedom is earned through discipline, and Guardiola’s tactical system requires players to operate with precision, patience, and positional awareness.
Grealish took time to adjust, but he embraced the challenge. He developed into a more complete player, one who could retain possession under pressure, recycle the ball intelligently, and contribute to City’s pressing schemes. His role on the left wing became less about attacking moments and more about control, width, and balance. In a side where collective performance is greater than individual flair,
The 2022–23 season was the best season in Grealish’s City career, the campaign that silenced (most) doubters and should have cemented his status as a key figure in one of the greatest teams in English football history. Grealish started 28 league games that season, more than any other City winger, and was integral to the team’s Premier League triumph.
His contributions were not limited to goals and assists. Grealish’s ability to draw defenders, create overloads, and maintain attacking shape allowed teammates like Erling Haaland and Kevin De Bruyne to thrive.
In the Champions League, he played a pivotal role in the knockout stages, including in the demolition of Real Madrid in the semi-final second leg, a performance many regard as one of the finest in City’s modern era.
He ended the season not just as a squad player, but as a first-choice starter in the biggest matches. Jack Grealish was not a flop and if this is it, we as City fans should thank him for the time and memories.