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Jack Grealish has a huge decision to make this summer.

The 29-year-old’s £100m move to Man City in 2021 has not worked out for the winger, and that has been evident this year as the Englishman has fallen down the pecking order at the Etihad Stadium, with Pep Guardiola handing him only one start in the Manchester club’s last 21 Premier League games.

That is not enough for a player of Grealish’s stature, and it has resulted in Ally McCoist urging the winger to leave Man City this summer in search of more minutes.

The 29-year-old will have ambitions to represent England at the 2026 World Cup, and should he sit on the bench for another year in Manchester, the former Aston Villa star will not find himself in Thomas Tuchel’s squad.

Several clubs are having a look at Grealish, but one is more realistic than the others, and they are trying to find a way to sign the City star this summer.

AC Milan is a realistic destination for Jack Grealish

AC Milan have shown interest in Grealish for months, and the Man City star could be an option for the Serie A club to replace Rafael Leao should the Portuguese star leave the San Siro ahead of next season.

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Speaking on the Transfers From Paradise Podcast, Dean Jones has stated that Milan are a realistic option for Grealish to continue his career next season, with the transfer journalist finding it hard to see the winger moving to Tottenham.

“Meanwhile, Jack Grealish has been linked (to Tottenham), but that feels far-fetched given his price tag,” Jones said about the Englishman’s future.

“AC Milan are a more realistic suitor. If there’s a gap in their squad, they’re interested. And for Grealish, it might actually be the perfect time to test himself abroad. He could thrive in Serie A’s rhythm.”

Grealish is happy at Man City, but he will know by now that he needs to move to save his career and hopes of playing at the 2026 World Cup.

Milan would be an exciting club for the Man City star to continue his story, and if he goes down this route, the 29-year-old would have taken to the advice of Gary Neville.

Gary Neville encourages Jack Grealish to leave the Premier League

Speaking on Stick To Football last week, Neville told Grealish that he should consider a move abroad this summer as it would keep the winger out of the spotlight of the English media, which is something Trent Alexander-Arnold seems keen to do with his move to Real Madrid.

Serie A would suit the Man City star’s game as it is slower than the Premier League and is more tactical, which would allow AC Milan’s manager to use the 29-year-old in many ways.

From a trophy point of view, things could not have gone better for Grealish at Man City; however, individually, the winger has struggled to showcase all of his ability on a consistent basis.

The 2025/26 season is very likely to see the Englishman start a new chapter in his career, but it remains to be seen where that will be.

Manchester City have been linked with Tottenham Hotspur star Destiny Udogie in recent months.

Fabrizio Romano reported in April that City are looking for a new full-back and Udogie is a target.

Romano claimed that Manchester City director Hugo Viana “appreciates” the Tottenham star and has been tracking him since his time at Udinese.

Now, Udogie has been directly asked about the transfer speculation involving him and City, and he has given his response.

Manchester City target Destiny Udogie says he’s just ‘trying to help’ Tottenham

Destiny Udogie has spoken to the media ahead of Tottenham’s Europa League final with Manchester United next week.

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Hayters TV told Udogie that he has had an “excellent season” and wondered whether links between him and City are a “nice thing to hear”.

The Tottenham ace responded by saying he feels he’s had a “tough season” but that his goal is to help “his team and that’s it”.

Udogie said: “No, I think personally it’s been a tough season with injuries and everything catching up with the form.

“At the same time we’re trying to finish the season strongly, so I’m trying to help my team and that’s it.”

Admittedly, City will find it difficult to sign the Spurs ace this summer, even though Udogie is a player who has impressed Pep Guardiola.

Sky Germany’s Florian Plettenberg has reported that Spurs want to keep Udogie next season and that he remains a key player for the London outfit.

This is why Tottenham have not set a price for the Italian star, added Plettenberg.

This will be a blow for Pep Guardiola, even though it’s not all that surprising. However, City appear to have alternatives.

City have shown long-term interest in Juventus full-back Andrea Cambiaso, while Eintracht Frankfurt’s Nathaniel Brown is also liked by City.

The Athletic’s Sam Lee recently spoke about Man City’s plans for the summer transfer window.

Lee, speaking on the Athletic FC Podcast, said City are looking to make a further “four or five signings” to go with the busy January transfer window they had.