Jack Grealish, the charismatic England international whose flair and flair have made him a fan favorite, finds himself at a career crossroads as the 2025 summer transfer window heats up. The 29-year-old Manchester City winger, once the cornerstone of a £100 million transfer from Aston Villa in 2021, is increasingly linked with a move to Everton, a club poised for a new era under manager David Moyes and the ambitious Friedkin Group ownership. With Grealish’s role at City diminishing under Pep Guardiola, a move to Merseyside could offer the creative spark Everton desperately needs and a chance for Grealish to reignite his career ahead of the 2026 World Cup.
Grealish’s journey at Manchester City has been a tale of brilliance and frustration. During the 2022-23 season, he played a pivotal role in City’s historic treble, starting in the FA Cup final and all seven Champions League knockout ties. His streetwise swagger and ability to create space, as noted by former Everton and Aston Villa CEO Keith Wyness, set him apart. “I’ve never seen a player receive a ball and make himself an extra yard in the way that he just controls it,” Wyness remarked, reflecting on Grealish’s time at Villa, where he renegotiated the player’s contract. However, injuries, including a hamstring issue in 2023-24, and competition from new signings like Jeremy Doku, Savinho, and Omar Marmoush have seen Grealish’s playing time plummet. Last season, he started just seven Premier League matches, logging a mere 715 minutes, with more yellow cards (seven) than goals and assists combined (six). His omission from City’s Club World Cup squad in 2025 further signaled that Guardiola sees no long-term future for him at the Etihad.
Everton, under Moyes’ stewardship, view Grealish as a transformative addition to a squad craving creativity. The Toffees have struggled offensively, with a 3-0 pre-season loss to Bournemouth exposing their lack of depth and flair. Moyes, who praised Grealish in 2021 as “probably the best player in the Premier League at this time,” believes he can unlock the winger’s potential by granting him the freedom he lacks in City’s rigid system. “I think with Moyes giving him a bit more freedom than he might get at City, this would work,” Wyness stated, highlighting the tactical fit. Everton’s move to the state-of-the-art Hill Dickinson Stadium in 2025, coupled with the financial backing of the Friedkin Group, adds allure to the project, making it an enticing destination for a player seeking a fresh start.
The prospect of staying in the northwest is a significant factor for Grealish, who values family stability. Living in Cheshire with his partner Sasha Attwood and their young daughter, Grealish is described as a “homebody” by Wyness, who dismisses the playboy image often associated with the winger. “I didn’t think there’d be any hope of him going to Saudi or things like that because Jack is a real homebody and very family-oriented,” Wyness noted, emphasizing Grealish’s preference to remain close to home. Everton’s proximity, just a short commute from Cheshire, makes the move logistically appealing compared to interest from clubs like Napoli, West Ham, or Bayer Leverkusen. A loan deal is the most likely scenario, given Grealish’s £300,000-a-week wages, which pose a significant hurdle for a permanent transfer unless he agrees to a substantial pay cut.
Despite his affection for Manchester City—evident when he told fans at an Oasis concert in Heaton Park, “I love City more than anything. And do you know what I love more than anything? City fans! They’re the best fans in the world!”—Grealish’s need for regular football is pressing. His exclusion from England’s recent squads underscores the urgency to rediscover his form to secure a spot in the 2026 World Cup. Everton offers a platform to be a “big fish in a small pond,” with fewer competitors for his preferred left-wing role compared to Newcastle, where Anthony Gordon and Harvey Barnes occupy similar positions. Posts on X suggest Grealish is “very open” to the move but wants assurance that Everton’s squad will be strengthened, with Jordan Pickford reportedly advocating for the transfer.
Everton’s transfer activity reflects their ambition. Alongside Grealish, they are pursuing Lyon’s Malick Fofana and have signed Thierno Barry, Mark Travers, and Adam Aznou, while making Carlos Alcaraz’s loan permanent. However, the departure of key players like Dominic Calvert-Lewin and Abdoulaye Doucoure highlights the need for a marquee signing like Grealish to galvanize the squad. While some, like Gabby Agbonlahor, suggest Grealish could explore European clubs like Bayern Munich, the consensus leans toward Everton as the ideal fit to revive his career. As Moyes navigates a challenging market, landing Grealish could signal Everton’s intent to compete at a higher level, offering fans a glimpse of the flair and excitement they’ve long craved.
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