Jack Grealish reacts to wonderful announcement made by Tottenham favourite James Maddison

Jack Grealish was quick to react to a new Instagram post shared by Tottenham favourite James Maddison.

Tottenham were interested in signing Grealish over the summer.

However, Spurs ultimately decided on Xavi Simons while the England international transferred to Everton on loan.

The Lilywhites met Grealish this season in Tottenham’s 3-0 win over Everton at Hill Dickinson Stadium, and while Spurs dominated, the left winger still had his moments.

Given Simons’ disappointing start and Grealish’s standout performances for the Toffees, there will no doubt be Tottenham fans regretting that their club did not sign the latter when they had the chance.

Jack Grealish looking downbeat in Everton home shirt
Credit: Imago

James Maddison welcomes the arrival of twins

Maddison has been sidelined for Tottenham after sustaining an ACL injury during a pre-season friendly against Newcastle United in August.

His absence from the team has been felt. Indeed, Spurs registered just 0.10 expected goals in their 1-0 defeat to Chelsea last Saturday.

This has largely been attributed to a lack of creators, with both Maddison and Dejan Kulusevski injured.

In the meantime, Maddison has reached a huge life milestone, taking to Instagram on 3 November to celebrate the birth of his twins.

While tagging his wife, he said: “Jensen and Frankie Maddison 30.10.25. Five-a-side team complete. You’re a superwoman.”

Several of his Tottenham and England teammates responded with the news, with Grealish liking the post in support.

Tottenham could have done with Jack Grealish this season

It is no secret that Tottenham have struggled creatively this season, with Simons unable to bridge the gap left behind by Maddison.

Despite a rocky start, Wilson Odobert has begun starting consistently on the left wing for Thomas Frank.

However, he is still raw and unpolished:

Meanwhile, Grealish has scored once and has provided four assists in the top flight this season.

Odobert needs time, and fans are prepared to give him that, but in the meantime Spurs are without an experienced left winger – and it shows.

Supporters are therefore left to wonder what could have been if it were Grealish, not Simons, who arrived over the summer.

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