About three years ago, I saw Jack Grealish in the pub in Sutton Coldfield. He was just a good, down-to-earth lad. Talking to people, getting rounds in, and bantering with the locals. He was at the time after moving from Villa to Manchester City for a British record fee.

Now, however, the same player has just rocked up on loan at Everton.  Mental how football works, isn’t it?

How We Got Here

Jack Grealish has completed his move to Everton on a season-long loan from Manchester City. The agreement incorporates a £50 million option to buy, which shows City haven’t completely written him off. Well, it’s not quite the way anyone envisaged things playing out for England’s most expensive ever player.

The boy has barely seen any action at City this season. Started only one Premier League game in 2024/25. One! That is an absolute joke for a player who cost £100 million. Pep Guardiola even sort of let him know he needed to step it up, not long ago. Guess that time ran out.

My mate who supports City reckons Grealish never really fitted into Pep’s system. “Too individual, not robotic enough,” he said over a pint last week. Harsh, but probably true.

Pep’s Problem Child

That was the sign it wasn’t going to work, and when Grealish failed to even make the bench for City’s trip to Fulham on the final day of last season, his exit seemed inevitable. Next, he was left out of the FIFA Club World Cup squad. That is about as explicit a statement as you could hear from a manager.

Pep apparently wanted him to be more consistent, more disciplined. Except that is not really what Jack Grealish is all about. The lad’s a flair player who does things on instinct.  You cannot programme this kind of talent like a computer.

Watch any Villa fan talk about Grealish from his early days. They’ll tell you he was magic because he played with freedom. He’d pick up the ball, run at defenders, and make things happen. That’s not really Pep’s style, though, is it?

The irony is that City won the Champions League in Grealish’s first season. He played his part in that. But football moves fast, and if you’re not in the manager’s plans, you’re out.

David Moyes’ Masterstroke

Fair play to David Moyes for pulling this off. Getting Jack Grealish on loan is a proper coup for Everton. The lad needs regular football; Everton needs creativity. Perfect match, really.

Moyes has always admired Grealish, apparently. Makes sense. The Scottish manager likes players with character, and Grealish has that in spades. Plus, he’s getting a £100 million player on loan. Not bad for a team that’s been struggling financially.

The Everton fans I know are buzzing about this. “Best signing we’ve made in years,” one of them told me. He’s probably right. When did they last get a player of this calibre?

Grealish could make his debut against Leeds on August 18th. That’s going to be some atmosphere at Elland Road. The Leeds fans will give him a proper stick, but that’s exactly what he needs. No hiding, no easy games. Proper football.

What Went Wrong at City?

It’s mad how Jack Grealish’s time at City has panned out. When he signed for £100 million in 2021, everyone thought it was perfect. English player, Premier League proven, exactly what City needed.

But Guardiola’s system is so specific. Every player has to be in exactly the right position at exactly the right time. That’s not really Grealish’s game. He’s at his best when he’s got freedom to roam, pick up the ball wherever, and beat his man.

The stats don’t lie either. In his final season at Villa, Grealish had 10 goals and 10 assists in the league. At City, his best season was 11 goals and 7 assists across all competitions. Not terrible, but not exactly what you’d expect from a £100 million player.

My dad, who’s watched football for fifty years, always said Grealish reminded him of George Best. “Too much talent for his own good sometimes,” he used to say. Maybe he was onto something.

The Everton Opportunity

This move to Everton could be exactly what Jack Grealish needs. Regular football, a manager who believes in him, and fans who’ll appreciate what he brings. No pressure to fit into a rigid system.

The £300,000-a-week wages are being subsidised by City, which is the only way Everton could afford this. Shows how much the City want him off their books. Their loss, Everton’s gain.

Alan Shearer reckons Grealish will be “demanding” at Everton. In a good way. He’ll want the ball and want to make things happen. That’s exactly what Everton have been missing.

The Premier League is better when players like Grealish are playing regularly. We need flair players, risk-takers, someone who can do something different. He’s been wasted sitting on City’s bench.

The Bigger Picture

The whole Jack Grealish situation shows how mental modern football has become. A £100 million player can become surplus to requirements in just four years. That’s the level City are operating at now.

But it’s also a reminder that money doesn’t guarantee success. Grealish wasn’t a flop at City exactly, but he never really hit the heights everyone expected. Sometimes the fit just isn’t right.

For England, this move could be massive too. Gareth Southgate always liked Grealish when he was playing regularly. If he gets back to his best at Everton, he could force his way back into the national team.

The timing’s perfect with the World Cup coming up. Grealish at his best is still one of England’s most dangerous attacking players. We saw that at the Euros when he was fit and confident.

What Success Looks Like

If Jack Grealish can get back to his Villa form at Everton, this loan will be a massive success for everyone involved. Ten goals, ten assists, that sort of output. Plus the entertainment factor.

Everton fans deserve something to get excited about. They’ve had years of mediocrity and relegation battles. A player of Grealish’s ability could transform their season.

For Grealish himself, it’s about proving he’s still got it. At 29, he’s entering his prime years. This could be his last chance to show he belongs at the top level.

The £50 million option to buy shows there’s still belief there. If he has a stormer this season, Everton might just find a way to make it permanent. That would be some story.

Football’s all about second chances. Jack Grealish is getting his at Goodison Park. Let’s see what he does with it.