Tottenham Hotspur’s pre-season preparations took a devastating hit during a 1-1 draw against Newcastle United in Seoul, South Korea, as star midfielder James Maddison was stretchered off with a serious knee injury, casting a shadow over what was meant to be a celebratory farewell for departing captain Son Heung-min. The 28-year-old England international, who had just returned from a season-ending knee injury sustained in May 2024, appeared distraught, clutching his face as medical staff attended to him on the pitch. New Spurs manager Thomas Frank described the moment as “brutal,” confirming the injury was to the same knee that sidelined Maddison for the Europa League final. “Sometimes in life and football things can be both beautiful and brutal,” Frank said, capturing the bittersweet emotions of the day as Son received a guard of honour from both teams for his final appearance after a decade with the club.
Maddison’s injury, which occurred just nine minutes after he entered as a 75th-minute substitute, has sparked immediate action from Tottenham’s recruitment team. With the 2025-26 Premier League season looming, the club swiftly contacted Manchester City to enquire about the availability of Jack Grealish, the 29-year-old winger who has struggled for game time under Pep Guardiola. “It looks like with Madders a bad injury,” Frank admitted post-match, underscoring the urgency to bolster the squad’s attacking options. Tottenham’s interest in Grealish, who started only seven Premier League matches last season, reflects their need for a creative spark to fill the void left by Maddison and Son, who is reportedly set to join LAFC. The club’s proactive approach comes after a failed attempt to sign Nottingham Forest’s Morgan Gibbs-White, whose £60 million release clause was thwarted by legal threats and a new contract with Forest.
The injury to Maddison, a pivotal figure in Tottenham’s midfield, compounds an already challenging summer. Spurs have made significant signings, including Mathys Tel, Mohammed Kudus, and Joao Palhinha, but the loss of Son and the potential long-term absence of Maddison, coupled with Dejan Kulusevski’s ongoing recovery from knee surgery, leaves the squad critically short in attacking areas. Maddison’s history of injuries—15 during his time at Leicester and 11 matches missed last season—heightens concerns about his reliability. His emotional response, seen as he limped to the touchline with his head in his hands, resonated with teammates, particularly Son, who was visibly shaken on the bench. “It’s most likely he has a bad injury, we need to be honest with that,” Frank said, awaiting a full medical assessment but bracing for a lengthy layoff.
Grealish, a £100 million signing for City in 2021, offers a potential solution. Despite his limited role last season, where he was outshone by Jeremy Doku and Savinho, his ability to create space and dictate play could thrive in Frank’s 4-2-3-1 system, where he would have more freedom as a No. 10. “I’ve never seen a player receive a ball and make himself an extra yard in the way that he just controls it,” former Villa CEO Keith Wyness said of Grealish, endorsing his fit for Spurs. A loan move appears the most feasible option, given Grealish’s £300,000-a-week wages, though City are open to reasonable offers for a permanent deal. Interest from Napoli has faded, positioning Tottenham as frontrunners, especially as Grealish, a family-oriented “homebody,” prefers to stay in the northwest, close to his Cheshire base.
The emotional weight of Son’s departure, marked by tears from the 33-year-old and a 66,000-strong crowd in Seoul, added poignancy to the match. “I think it’s very likely Sonny’s last game because it’s very close,” Frank noted, reflecting on the South Korean’s 173 goals in 454 appearances and his Europa League triumph. As Tottenham face Bayern Munich and the UEFA Super Cup against Paris Saint-Germain next, the absence of Maddison and Son underscores the urgency of their transfer pursuits. Grealish’s potential arrival could not only fill a tactical gap but also signal Spurs’ ambition under Frank, who aims to build on last season’s Europa League success. With Brennan Johnson and Dominic Solanke leading the attack, and new signings integrating, Tottenham’s swift enquiry for Grealish reflects their determination to navigate this crisis and emerge stronger.
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