Tottenham begin talks to sign special City player who wanted Spurs move in 2018 after shock Maddison injury
The ripple effects of James Maddison’s knee injury have sent Tottenham scrambling for creative solutions, with the North London club making a surprise approach for Manchester City outcast Jack Grealish.
Sources confirm Spurs have initiated contact regarding the England international’s availability after manager Thomas Frank described Maddison’s setback as “brutal,” reigniting concerns about the playmaker’s recurring fitness issues.
Grealish finds himself at a career crossroads following Pep Guardiola’s decision to make him available this summer, with City open to both permanent and loan deals for the 29-year-old.
The former Aston Villa captain has seen his Etihad stock plummet after failing to replicate his talismanic Villa Park form, despite collecting multiple Premier League medals.
With just two years remaining on his contract, the champions appear ready to cut their losses on a player whose £100 million price tag once made him British football’s most expensive acquisition.
Intriguingly, this isn’t the first flirtation between Grealish and Tottenham. The Birmingham-born attacker previously confessed his desire to join Spurs in 2018 while at Villa, admitting the collapsed move left him mentally unsettled during their Championship campaign.
“My head was swivelled,” Grealish revealed at the time, acknowledging Tottenham’s Champions League allure under Mauricio Pochettino.
That aborted transfer ultimately worked in his favor – he spearheaded Villa’s promotion before securing his dream City move – but the stars may finally align six years later under very different circumstances.
For Tottenham, Grealish represents both a short-term fix and long-term conundrum. His natural creativity and ball-carrying ability could help offset Maddison’s absence, while his Premier League pedigree offers reliability in a squad transitioning from Son Heung-min’s departure.
However, questions linger about whether the maverick winger can rediscover his best form after two underwhelming seasons at City, where Guardiola’s tactical demands often muted his free-spirited attacking instincts.
The potential deal carries financial complexities. While City may demand a substantial fee despite Grealish’s diminished role, Spurs could structure payments around performance incentives or explore an initial loan with obligation to buy.
Grealish’s wages present another hurdle, though Tottenham’s newfound financial flexibility after several years of prudent spending might accommodate his salary demands for the right terms.
Beyond the pitch, Grealish’s potential arrival would reunite him with close friend Maddison, whose injury ironically opened this opportunity.
Their off-field chemistry could aid dressing room integration, while Grealish’s big-game experience might prove invaluable for a Spurs side aiming to bridge the gap to the Premier League’s elite.
As negotiations progress, Tottenham must weigh Grealish’s undeniable talent against his recent stagnation.
Is he the marquee signing to propel Thomas Frank’s project forward, or an expensive gamble on past glories?
For Grealish, the move represents a chance to reboot his career as a central figure rather than a peripheral one – an opportunity he once dreamed about at Tottenham Hotspur Stadium, albeit under vastly different circumstances.
The coming days will reveal whether this long-delayed transfer finally materializes when both club and player need it most.