As the summer transfer window looms, Jack Grealish’s future at Manchester City appears increasingly uncertain, with the England international seemingly on the verge of a dramatic exit from the Etihad Stadium. The 29-year-old winger, once heralded as a cornerstone of City’s attack, has struggled to secure a regular starting role under Pep Guardiola, prompting speculation about a potential move to Serie A champions Napoli. With the Italian club’s interest intensifying under the guidance of manager Antonio Conte, Grealish’s next chapter could see him reignite his career in Naples, following in the footsteps of other British stars who have thrived in Italy’s top flight.
Grealish’s journey at Manchester City began with a blaze of promise in 2021, when the club paid a record-breaking £100 million to secure his services from boyhood club Aston Villa, making him the most expensive English player at the time. His flair, creativity, and knack for unlocking defenses were expected to mesh seamlessly with Guardiola’s tactical system. “Pep loves the way he plays, and we all feel he is an ideal fit for Manchester City,” said City’s director of football Txiki Begiristain at the time. Yet, despite contributing to City’s historic 2022-23 treble-winning campaign, Grealish has struggled to replicate the free-spirited brilliance he displayed at Villa. His role has been curtailed, with just seven Premier League starts this season and a mere four minutes across City’s final seven league matches. His absence from the squad for the season-ending 2-0 win over Fulham and his benching during the FA Cup final loss to Crystal Palace underscored his diminishing status. “Of course Jack has to play,” Guardiola admitted post-Fulham. “He’s an unbelievable player that has to play football every three days. It didn’t happen this season and last season either. He needs to do it – with us or another place.”
Napoli, fresh off clinching their second Serie A title in three years with a 2-0 victory over Cagliari on May 23, 2025, have emerged as the frontrunners to sign Grealish. The club, led by Conte, sees the winger as a marquee addition to bolster their UEFA Champions League ambitions. Conte, a known admirer, believes Grealish’s technical ability and maverick style could thrive in the slower, more tactical pace of Italian football. The success of former Premier League players like Scott McTominay, who has scored 12 goals this season, and Billy Gilmour at Napoli has fueled optimism that Grealish could follow suit. However, financial hurdles loom large. Grealish’s £300,000-per-week wages and City’s reluctance to accept a loan deal pose challenges, with Napoli struggling to fund a permanent transfer. A potential loan with an obligation to buy, similar to deals structured for other high-profile signings, remains a possibility.
Grealish’s struggles at City stem from a mismatch between his natural flair and Guardiola’s structured system. At Villa, he was a free-roaming playmaker, registering 16 goal contributions in his final season. “There were very few teams that could stop Grealish in full flow,” one observer noted of his Villa days. Yet, at City, players like Jeremy Doku, Savinho, and January signing Omar Marmoush have overtaken him in the pecking order, limiting him to 1,521 minutes this season. His market value has plummeted to €35 million, a stark contrast to his £100 million transfer fee. Injuries, including a muscle issue during a Champions League clash against Real Madrid, and inconsistent form—marked by a goal drought in 2024 until a January FA Cup strike against Salford City—have compounded his challenges.
Despite interest from Premier League clubs like Tottenham, Newcastle, and even a sentimental return to Aston Villa, Grealish reportedly prefers a move abroad to escape intense media scrutiny in England. Tottenham’s Champions League qualification via their Europa League triumph and Newcastle’s financial backing make them viable options, but City are wary of strengthening domestic rivals. A return to Villa, where Grealish’s departure in 2021 eased their financial constraints, seems unlikely due to wage concerns and strained fan relations. “I’m absolutely sure that Unai Emery won’t be going anywhere near Jack Grealish,” said former Villa striker Stan Collymore, citing his diminished output. AC Milan and Saudi Pro League clubs have also been linked, but Napoli’s project under Conte appears the most enticing.
As Grealish approaches a crossroads, his 39 England caps and desire to reclaim a regular spot in the national team add urgency to his decision. “Jack might end up going somewhere like Saudi because I’m struggling to see a top four, five or six team that would take him,” Collymore warned, emphasizing the stakes for his international career. With his contract running until June 2027, Grealish’s camp is set for showdown talks with Guardiola to seek assurances about his role. The outcome will shape whether he remains a peripheral figure at City or embarks on a new adventure in Naples, where Conte’s vision could unlock the “free spirit” that once dazzled the Premier League.
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