Not every football story starts the way this one does.
Back in 2015, a 19-year-old Jack Grealish was on holiday in Tenerife after breaking into Aston Villa’s first team. What followed wasn’t exactly a highlight reel moment.
Photos surfaced of him lying in the street in San Eugenio, Adeje, clearly worse for wear. At the time, it spread everywhere… and for a lot of people, that became their first real introduction to him.
Not ideal.
From That Moment to Captain
The difference is… he didn’t disappear after that.
Grealish went back, worked his way up, and eventually became Aston Villa captain, leading them back into the Premier League and turning himself into one of the most talked-about players in England.
Same player… very different situation.
The £100 Million Move
Then came 2021.
Manchester City paid £100 million for him, making him the most expensive English player in history. Big fee, big expectations… and not always straightforward from there.
He had moments, but also spells where he drifted in and out of the team.
The Celebrations Everyone Saw
If there’s one thing that didn’t change… it was his reputation off the pitch.
After City won the Champions League, Grealish went on a celebration run that lasted well over 24 hours. Still in kit at 6am, onto Ibiza, back for the parade… the whole thing.
He later admitted he barely remembered any of it.
Some things stick.
A Dip… Then a Reset
After that high point, things slowed down.
Injuries, less game time, and a drop in form meant he wasn’t as central to City as before. Eventually, he ended up on loan at Everton in 2025, looking for a reset.
And to be fair, it worked.
Early performances, assists, and a bit of momentum again. Not the finished comeback story… but a step in the right direction.
Still Something to Prove
With the 2026 World Cup coming up, he’s still on the edge of the England squad.
Not guaranteed. Not written off either.
Which probably sums up his career quite well.
The Reality
From a night out in Tenerife that went too far… to becoming a £100 million player and European champion.
Messy at times, no doubt.
But not exactly forgettable.