The summer transfer window of 2025 has been a whirlwind for Manchester City, with Pep Guardiola overseeing a dramatic squad overhaul following a rare trophyless season. Among the high-profile departures, Jack Grealish’s move to Everton on a season-long loan, with a £50 million option to buy, marks a significant shift for the 29-year-old England international. The former Aston Villa star, once the most expensive British footballer at £100 million, has bid an emotional farewell to the Etihad Stadium, responding to a heartfelt message from his close friend and teammate Kalvin Phillips, who remains sidelined by injury but faces his own uncertain future at City.
Grealish’s departure comes as part of Guardiola’s broader strategy to reshape a squad that struggled in the 2024/25 Premier League campaign, finishing third after a title-winning run the previous season. The arrival of dynamic wingers like Jeremy Doku and Savinho, coupled with Grealish’s limited game time—1,716 Premier League minutes since the 2023/24 season—and persistent injuries, pushed him down the pecking order. Despite his undeniable talent, showcased during City’s 2022/23 continental treble, Grealish found it challenging to adapt to Guardiola’s tactical demands. Reflecting on his debut season at City, he admitted, “Adapting to the club’s style of play had been much more difficult than I imagined.” Yet, his flair and charisma earned him defenders among teammates, with Kevin De Bruyne noting that Grealish was “an easy target for criticism” due to the media spotlight on English players, and İlkay Gündoğan calling him “so misunderstood by some of the media.”
The move to Everton offers Grealish a chance to rediscover his spark under David Moyes at Goodison Park, now rebranded as Hill Dickinson Stadium. The loan deal, finalized in early August 2025, has sparked excitement among Everton fans, who see Grealish’s creativity and Premier League pedigree as a potential catalyst for their season. However, his hefty £300,000-a-week wages posed a hurdle, with negotiations requiring compromises from both clubs. Former Everton CEO Keith Wyness suggested the Toffees might push for a cut-price permanent transfer if Grealish’s loan proves successful, rather than triggering the £50 million clause. Interest from West Ham and Newcastle United also surfaced, but Everton secured the deal, banking on Grealish’s ability to revive his career in a new environment.
Kalvin Phillips, Grealish’s long-time friend and England teammate, was among the first to send his support. Currently recovering from Achilles surgery, Phillips posted on his Instagram story on August 12, writing, “All the best my brother! Go smash it.” Grealish, visibly moved, reshared the post and responded simply, “My brother,” encapsulating their deep bond forged through shared England camps and their time at City. The duo’s friendship has been a constant, with Grealish previously playing a pivotal role in convincing Phillips to join Manchester City from Leeds United in 2022 for £45 million. Their camaraderie extends beyond the pitch, with lighthearted moments like Grealish teasing Phillips about his “moon boots” during a 2022 injury recovery, highlighting their playful rapport.
Phillips’ own future remains in limbo. After loan spells at West Ham and Ipswich Town, where he made 19 Premier League appearances in 2024/25 but couldn’t prevent Ipswich’s relegation, the 31-cap England midfielder is not expected to return to action until late August. Speculation about a permanent move back to his boyhood club, Leeds United, now back in the Premier League, has intensified, but no deal has materialized. Phillips’ limited impact at City—31 appearances since 2022—mirrors Grealish’s struggles, as both players have been overshadowed by City’s influx of new talent, including signings like Rayan Ait-Nouri, Rayan Cherki, and Tijjani Reijnders.
Grealish’s move to Everton is a fresh chapter for a player often compared to Paul Gascoigne for his flair and larger-than-life personality. He once expressed admiration for Gascoigne, saying, “I’d love to be like Gazza. He played with such joy.” As he prepares to make his mark on Merseyside, Grealish’s focus is on recapturing that joy, free from the weight of City’s expectations. Meanwhile, Phillips, still tethered to City’s bench, watches his friend’s departure with hope and encouragement, a reminder of the personal connections that endure amid the ruthless business of football transfers.
As Manchester City gear up for the 2025/26 season, with the Club World Cup looming, the exits of Grealish, Kevin De Bruyne (now at Napoli), and potentially others like James McAtee signal a new era. For Grealish, Everton represents not just a new club but a chance to prove his critics wrong, with Phillips’ words ringing in his ears: “Go smash it.”
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