In the ever-churning world of Premier League transfer rumors, few stories have captured attention quite like the potential departure of Jack Grealish from Manchester City. The 29-year-old England international, once heralded as a cornerstone of City’s treble-winning campaign in 2023, now finds himself at a crossroads. With limited game time under Pep Guardiola and a surprising omission from City’s Club World Cup squad, speculation about Grealish’s next move has reached fever pitch. Among the frontrunners to secure his signature is Tottenham Hotspur, with whispers that a unique WhatsApp group could play a pivotal role in sealing the deal.
Grealish’s journey at Manchester City has been a rollercoaster. After his record-breaking £100 million transfer from Aston Villa in 2021, he quickly became a fan favorite, dazzling with his flair and contributing significantly to City’s historic treble. His 2022-23 season was a high point, with five goals and seven assists in 28 Premier League matches. However, the 2024-25 season painted a different picture. Grealish started just seven league games, scoring once and providing a single assist. His reduced role, coupled with Guardiola’s decision to exclude him from the Club World Cup, has signaled that his time at the Etihad may be drawing to a close. “What happens I don’t know, but if he doesn’t (leave), he is a player for Man City and he will be back,” Guardiola said, leaving the door slightly ajar but fueling speculation about an imminent exit.
Tottenham have emerged as the favorites to land Grealish, with betting odds placing them ahead of rivals like Newcastle, Everton, and even a potential return to Aston Villa. The prospect of Grealish joining Spurs is tantalizing, not least because of his close friendship with Tottenham’s James Maddison. The pair, along with Ross Barkley, John McGinn, Dele Alli, and Ben Chilwell, are part of a lively WhatsApp group dubbed “The Avengers.” Grealish revealed in a 2021 interview with UMM, “Me or Madders [are the most vocal]. On that point, Maddison is on the group chat 24/7. Someone writes in it and then bam, he’s ready straight away. Constantly in there. Then there’s people like Chilly, he’d be online and he wouldn’t read it.” The group, formed during a winter break in Dubai, has become a symbol of camaraderie among England’s footballing elite, with members celebrating goals by flashing an “A” symbol with their hands.
This tight-knit connection could prove crucial. Maddison, now a key figure at Spurs, is reportedly advocating for Grealish to join him in North London. “Could the latter put a good word in for him at Spurs?” pondered one insider, highlighting the potential influence of their bond. A move to Tottenham would see Grealish reunite with his England teammate under manager Thomas Frank, whose attacking style could rejuvenate the winger’s career. Spurs, fresh off a strong campaign, are keen to bolster their squad, and Grealish’s versatility and creativity make him an ideal fit.
However, Tottenham face competition. Everton have emerged as a surprise contender, with their new ownership group, the Friedkin Group, viewing Grealish as a statement signing for their move to the new Bramley-Moore Dock stadium. “The glamour of the club’s new stadium and the possibility of a regular starting role is attractive to the former Aston Villa star,” noted one observer. Newcastle, backed by their Champions League ambitions, and Bayer Leverkusen, seeking a replacement for Florian Wirtz, are also in the mix. Even Serie A champions Napoli have shown interest, with Kevin De Bruyne reportedly giving Grealish a “thumbs up” for a potential move to Italy. Yet, Grealish’s £300,000-a-week salary poses a hurdle, with clubs like Napoli likely only able to afford a loan deal unless City subsidize his wages.
The transfer saga is further complicated by Grealish’s desire to secure regular playing time ahead of the 2026 World Cup. New England manager Thomas Tuchel has made it clear that consistent club football is a prerequisite for a national team recall, adding urgency to Grealish’s decision. Despite his struggles, his talent remains undeniable. “Grealish is a real talent who still has the capability to exert great influence on games,” said BBC Sport’s Phil McNulty, reflecting the sentiment that a change of scenery could unlock his potential.
As the transfer window unfolds, the football world watches eagerly. Will Grealish’s WhatsApp banter with Maddison pave the way for a blockbuster move to Spurs? Or will another club swoop in to secure the services of the charismatic winger? One thing is certain: Grealish’s next move will be a defining moment in his career, and the Premier League is braced for a shock transfer that could reshape the landscape of the top flight.
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