The summer transfer window of 2025 is heating up, and Tottenham Hotspur’s new manager, Thomas Frank, finds himself at the heart of a tantalizing dilemma. The north London club, fresh off a Europa League triumph but a disappointing 17th-place Premier League finish, is eyeing a blockbuster move for Manchester City’s outcast winger Jack Grealish. The 29-year-old Englishman, once the £100 million record-breaking transfer from Aston Villa to City in 2021, has reportedly made his preferences clear to Spurs, igniting both excitement and strategic debates within the club’s hierarchy. Grealish’s potential arrival could reshape Tottenham’s attack, but his hefty wages and positional demands pose a challenge for Frank’s vision.
Grealish’s time at Manchester City has been a rollercoaster. A key figure in their 2023 treble-winning campaign, he’s since struggled to secure a regular starting spot under Pep Guardiola, who has favored younger wingers like Savinho and Jeremy Doku. “Jack is an exceptional player,” Guardiola said during a recent Club World Cup press conference, but added, “The only reason why he didn’t play last season is, of course, my decisions.” Excluded from City’s Club World Cup squad, Grealish has accepted that his future lies elsewhere, with Tottenham emerging as a frontrunner. The Lilywhites’ Champions League qualification, secured through their Europa League win, makes them an attractive destination for the England international, who is keen to revive his career and cement his place in Thomas Tuchel’s World Cup plans.
Tottenham’s interest in Grealish is no fleeting rumor. Frank, who replaced Ange Postecoglou after a controversial sacking in June 2025, has given the green light to pursue the winger, having held “extensive” talks with club chairman Daniel Levy and sporting director Johan Lange about recruitment targets. Grealish’s name surfaced repeatedly, with Spurs already engaging his representatives. However, a major hurdle looms: his £300,000-per-week salary, which threatens to disrupt Tottenham’s wage structure. “There are not many teams around that can afford to pay him the wages he’s on at the moment,” noted football finance expert Stefan Borson, suggesting a loan deal or significant pay cut might be necessary. Everton and Newcastle are also in the race, but Spurs’ European pedigree gives them an edge.
The intrigue deepens with Grealish’s own input. He’s reportedly told Tottenham his preferred role is an inverted left forward in a 4-3-3, a position reminiscent of his dynamic days at Aston Villa. “I think the No 10 role is somewhere Grealish could play at Tottenham,” former Spurs right-back Alan Hutton speculated, suggesting he could fill in centrally if James Maddison falters. This flexibility poses a dilemma for Frank, who’s already secured Mathys Tel’s permanent £30 million transfer from Bayern Munich to bolster the left flank. With Son Heung-min, at 33, potentially nearing a move to Al-Hilal, Grealish could be a long-term solution, but his integration requires tactical finesse. Frank’s high-pressing, vertical system demands aggressive off-ball running and quick releases—areas where Grealish, criticized for dawdling at City, must adapt.
Frank’s track record at Brentford, where he boosted players like Bryan Mbeumo’s market value by €51.5 million, fuels optimism that he could unlock Grealish’s flair. “He can become a ball carrier in transitional situations,” one analyst noted, envisioning Grealish combining with Maddison and overlapping full-back Destiny Udogie to overload half-spaces. Yet, the financials remain daunting. Manchester City, open to offers between £38-43 million, may subsidize a loan, but Grealish’s willingness to lower his demands is crucial. “It’s a dream come true to be part of this club,” Grealish said upon joining City in 2021, but his nightmare spell on the sidelines has him chasing regular minutes.
For Tottenham, Grealish represents a gamble with high reward. His creativity could elevate a squad aiming for a top-four finish, but Frank must balance ambition with pragmatism. As Spurs also target right-wingers like Antoine Semenyo and Eberechi Eze, the transfer window promises a squad overhaul. Grealish’s saga, blending star power, financial hurdles, and tactical intrigue, is one to watch as deadline day looms on September 1, 2025.
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