Tottenham Hotspur are reportedly gearing up to make an ambitious bid for Manchester City’s Jack Grealish this January. While this isn’t the first time the North London club has targeted the talented winger, the potential move has rekindled interest among fans, especially given Grealish’s own reflections on a missed opportunity to join Spurs years ago.
Tottenham’s Renewed Interest in Jack Grealish
The recent buzz around Grealish to Tottenham has gained traction thanks to a report from Football Transfers, which revealed that Tottenham are actively engaged in talks with Grealish’s representatives about a possible switch in the winter transfer window. Spearheading this pursuit is Tottenham’s technical director Johan Lange, who has a history with Grealish from their days at Aston Villa. Lange’s positive relationship with the player is seen as a significant advantage as Spurs attempt to lure the England international to North London.
Tottenham manager Ange Postecoglou is also believed to be a major proponent of this move. Reports suggest that Postecoglou views Grealish as a versatile asset capable of bolstering Spurs’ offensive options, particularly in positions currently held by star players Heung-min Son and James Maddison. The 29-year-old Grealish could bring depth and competition to Tottenham’s attacking lineup, offering additional tactical flexibility.
Grealish’s Near-Move to Spurs in 2018
This isn’t Tottenham’s first effort to sign Grealish. Back in 2018, during a time when Aston Villa was struggling in the Championship, Spurs were close to securing the then up-and-coming talent. The transfer ultimately fell through, and Grealish stayed with Villa, helping them gain promotion to the Premier League in the 2018-19 season and going on to establish himself as one of the league’s top creative talents.
Reflecting on the failed move later that year, Grealish expressed his disappointment. Speaking to The Telegraph, he admitted that joining Mauricio Pochettino’s Spurs could have been a career-defining moment, potentially even earning him a call-up to the England national team by the year’s end. He recalled feeling unsettled at the time, saying, “At the start of the season, my head was swivelled, it was all over the place. Even after the transfer window closed, until the end of August, I wasn’t right.” His remarks offered insight into just how significant that missed move felt to him, suggesting that he had seen Spurs as a perfect fit for his ambitions at the time.
Concerns Over Grealish’s Fit in Postecoglou’s System
Despite the revived rumors, some analysts have raised doubts about Grealish’s potential role in Ange Postecoglou’s Tottenham system. Unlike the typical Postecoglou winger, known for high-paced, direct play, Grealish is more of a possession-oriented player, skilled at drawing defenders and creating space through patient build-up rather than explosive bursts. With Tottenham already well-staffed in the attacking midfield and winger roles—including players like Dejan Kulusevski, James Maddison, and young talent Lucas Bergvall—it’s uncertain where Grealish would fit in without disrupting the team’s current dynamic.
Additionally, Tottenham have recently favored a youth-focused recruitment strategy, bringing in players who align with a younger age profile. At 29, Grealish falls outside that range, which might make his acquisition an exception to the club’s recent transfer priorities. Given these factors, some believe this rumored move lacks viability, despite the club’s interest.
While the idea of Grealish in a Spurs shirt could appeal to fans, it remains to be seen if the interest will materialize into a concrete bid or simply fade like the previous attempt to bring him to North London. Nevertheless, Grealish’s skillset and experience would undoubtedly bring something unique to Tottenham’s ranks if both parties can find common ground.
