Tottenham Hotspur may finally be about to complete a transfer mission started back in 2018 at Aston Villa amid reported interest in Manchester City forward Jack Grealish.

Grealish joined City back in 2021 and while he will probably not be regretting his move to the north west, having won three Premier League titles, the Champions League, the FA Cup and the Club World Cup, his form has not often reached the heights that it did at Villa Park. When the winger was on the verge of exiting his boyhood club three years prior to his eventual exit, Grealish was eyed by Tottenham for a transfer.

Spurs were impressed by his first full season at Villa and they were keen to get a deal done under the manager at the time Mauricio Pochettino. However, Grealish decided to stick with the West Midlands side, and postponed his departure for City.

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Heading into the 2025 January transfer window, Grealish has managed just two assists, in all competitions, this season and this has led to speculation that City could be looking to sell. According to The Daily Mail, Spurs have returned to monitor Grealish along with Newcastle United.

As things stand, it's unclear whether City will actually sanction a sale in January, next summer or even at all. Villa's fortunes have changed considerably since Grealish left the club and they are unlikely, at this stage, to offer the 29-year-old a return back to the West Midlands.

The January transfer window opens on New Year's Day. It will close again on Monday, February 3.