The 2018 Jack Grealish moment that could have changed his entire career

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Jack Grealish is an exceptional footballer.

The England international is proving his immense talent on loan at Everton from Manchester City so far this season, scoring one goal and providing four assists in seven Premier League appearances.

If Jack Grealish can maintain his exquisite form, the £100m man will surely book his spot at the FIFA World Cup this summer and add to his 39 caps for England – but his entire career could have turned out very differently after a dramatic moment in 2018.

When Aston Villa almost sold Jack Grealish to Tottenham for peanuts

Back in the summer of 2018, Aston Villa were in severe financial peril under Tony Xia.

Every single player at Villa Park was up for sale, even Grealish, after defeat to Fulham in the 2018 Championship play-off final plunged the Villans into uncertainty.

Daniel Levy – who has since left Tottenham – sensed an opportunity and immediately submitted a bid worth £3m plus Josh Onomah for Grealish.

It was rejected, but as Xia desperately attempted to sell an equity stake to bring some cash into Aston Villa quickly, there was an acceptance at Villa Park that the academy graduate would be sold to Spurs eventually once a respectable bid was made.

Grealish – who adores Tim Sherwood – was also ready to move to Tottenham, where Mauricio Pochettino was making waves in English football as an exciting side spearheaded by Harry Kane and Dele Alli made headlines.

However, before Levy came back to the negotiating table with a new bid, salvation had arrived in the form of Nassef Sawiris and Wes Edens – who remarkably purchased a controlling stake in Aston Villa within a few days, when such a takeover would typically need months to materialise.

It gave the Villans newfound financial security and the chance to keep Grealish, who ended up firing Aston Villa into the Premier League 12 months later, captaining his boyhood side to a 2-1 win over Derby in the Championship play-off final.

Just two years later, the Birmingham-born midfielder became the first £100m player in British football history when Manchester City moved to secure his signature in a club-record deal in August 2021.

Jack Grealish would probably still be at Tottenham if 2018 move went through

Of course, Grealish, who is close with Erling Haaland, could have still ended up becoming a £100m player had he sealed that move to Spurs in 2018 – although a transfer might not have been allowed.

Levy memorably rejected a £100m offer from Manchester City for Kane in June 2021, and later kept the striker until he only had 12 months remaining on his contract, sanctioning an £86.4m move to Bayern Munich in August 2023 instead of losing Tottenham’s record goalscorer on a free transfer.

Therefore, had Grealish moved to Spurs, there is no guarantee that he would have even been allowed to leave and become the first £100m player in English football history – so the timely intervention from Sawiris and Edens had a massive impact on his career, as well as his legacy in the game.