Tottenham Hotspur are reportedly exploring a January move for Jack Grealish, with sources suggesting this isn’t the first time the North London club has pursued the former Manchester City star. In the past, Grealish himself expressed disappointment over a failed move to Spurs, reflecting on how he saw a potential future there.
The news, first reported by Football Transfers, claims that Tottenham is in talks with Grealish’s representatives about a high-profile transfer. Spearheading the push is Johan Lange, who previously worked closely with the winger at Aston Villa and shares a strong rapport with him. According to the outlet, Ange Postecoglou admires Grealish’s versatility and believes he could provide valuable competition for both Heung-min Son and James Maddison.
This isn’t the first time Tottenham have come close to signing Grealish. In 2018, when Aston Villa were still in the Championship, the club nearly brought him to North London. Grealish eventually helped Villa secure promotion in the 2018-19 season and went on to make a significant impact in the Premier League.
Reflecting on the missed opportunity later that year, Grealish admitted, “Of course there’s going to be disappointment there. They’ve beaten Manchester United 3-0 at Old Trafford; they’re playing Barcelona in the Champions League next week,” he told The Telegraph. “I felt that if I’d gone there, I could have maybe been in the England squad by the end of the year. 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.”
However, doubts remain about Grealish’s fit in Postecoglou’s system. The English winger is not typically suited to the style that the Spurs manager prefers, especially considering Tottenham’s solid options in attack, including Dejan Kulusevski, James Maddison, and Lucas Bergvall in reserve. Additionally, at 29, Grealish doesn’t align with the younger profile that Tottenham has favored in recent years, casting further uncertainty over the likelihood of this transfer.
