Britain's first £100m man facing defining moment

When Jack Grealish breezed back into Everton in his white Lamborghini one hour before the end of this summer's transfer deadline, the excitement among supporters and the player himself was clearly evident.

Grealish's previous spell on loan from Manchester City had been cut short by a serious foot injury, but the 31-year-old had produced enough moments of excitement to make his return to the Finch Farm training base a rare moment of joy amid a miserable summer in the transfer market.

When Grealish finally left in the early hours - with the deal done, every autograph signed and every selfie posed for - it was a sort of homecoming for an everyman personality Everton fans had come to regard as one of their own.

This was a move with a lot riding on it - for Everton manager David Moyes, who had been left with only 18 senior players after a botched transfer window, and especially for Grealish, whose exile from City at the start of the final year of his contract confirmed his banishment.

Now, Grealish's future and Everton's faith in him, has reached a defining moment.

Grealish's exclusion from Everton's squad before the Carabao Cup tie at home to Newcastle was publicly described as "a breach of club discipline".

Specifically, it was a failure to turn up for training on Monday, leaving the talented maverick - who was Britain's first £100m footballer when he signed for City from Aston Villa in summer 2021 - facing another rebuild in his career.

Everton's decision to go public before the game with the reasons for Grealish's absence emphasised the seriousness of his transgression.

The fall-out means this now looks increasingly like Grealish's 'now or never' moment, because failure at Everton will surely mark a downward spiral from the top echelons of the Premier League.

Everton do not regard this week's misdemeanour as marking the proverbial 'Last Chance Saloon' for Grealish. Moyes does not have enough players at his disposal to make rapid outcasts of potential game-changers.

But it increases the pressure on the former England forward to win back the faith of fans who love his obvious enjoyment of life and the magic he has shown he can produce.

Moyes will hope it is a harsh lesson learned, because Everton now have even more to play for, given Wembley has suddenly come into view in the Carabao Cup.

BBC Sport believes there have been occasional time-keeping issues with Grealish in the past, but nothing on this scale from a personality regarded as a hard trainer who, in general, keeps himself in good condition.

Grealish has held talks with those in authority at Everton, where it is sure to have been made crystal clear there must be no repeat, certainly not under a strict disciplinarian such as Moyes, and he must now attempt to be rehabilitated back into the squad.

The inevitable decision to punish Grealish, taken at a high level within the club but with input and full support from Moyes, leaves him at the crossroads.

That is especially the case because Everton gave arguably their best performance of the season to beat Newcastle United 3-1 and set up a quarter-final at League Two Fleetwood Town, conquerors of Premier League champions Arsenal in the last round.

And it was done with the more dynamic style of 20-year-old Tyrique George playing on the left flank, which Grealish might have been expected to occupy.

Moyes was guarded after the game and instead preferred to focus on a vital victory.

"You probably know I'm not going to give any details. It's a club decision and I support it. It's something I don't want to speak too much about," he said.

"The one thing about Everton is that they have got real good values. All the players stand behind it and accept the values, on the pitch and off the pitch, and I think the players did a good job.

"It is a small squad, but we are doing our best to keep challenging. We are not accepting any excuses for anything and I think the players are doing a great job. There was a humility about us."

The words were not specifically aimed at Grealish, but they might as well have been from a manager who will have been bitterly disappointed and angry about his transgression.

Moyes and Grealish formed a close relationship from virtually their first moment of contact in August 2025, the latter saying: "As soon as I spoke to the manager, I knew there was only one place that I wanted to go and that was Everton."

And Grealish, a key figure when Manchester City won the Treble of Premier League, FA Cup and Champions League in 2023, played his part until sustaining a foot fracture that ended his season in Everton's 1-0 win at his former club Aston Villa in January.

Grealish's happiness with life at Everton was illustrated when he decided against returning to City, continuing his rehabilitation at Finch Farm rather than going back to Etihad Stadium.

Everton weighed up a second loan deal to bring Grealish back carefully, with his injury, finances and - to a certain extent - his character all entering the equation before Moyes decided to move again for a player who insisted Merseyside was the only place he wanted to be.

Moyes was also juggling very limited options as owners The Friedkin Group appeared to back away from serious squad strengthening as they prepared to put the club up for sale.

Grealish's form this season has been underwhelming, failing to score or create an assist in eight appearances - two of those at City before returning to Everton - while his tendency to slow play down is at odds with the usual tempo Moyes requires from his team.

Moyes' fury will have increased because Grealish, who missed Saturday's loss at Arsenal through "illness", is part of a paper-thin squad that simply cannot carry passengers or have players ruling themselves out through needless ill-discipline.

There will be frustration too, as Grealish is a hugely popular within Everton's dressing room as well as with staff in every area of the club. He has been described as "a lad with a heart of gold, kind and charming, who actually loves being here".

This was illustrated when he recently made a £10,000 donation to a GoFundMe page for Everton fan Leon Skapars, 36, a father of three who has been diagnosed with cancer.

The family are raising money in a search for treatment options, and Skapars' wife Crystal said: "In that moment, Jack gave our whole family something we desperately needed, hope. What he has done for our family is something we will never forget. It makes us feel incredibly emotional."

Grealish also appeared to present awards at the Daily Mirror's 'Pride Of Britain' event recently, saying: "Footballers are classed as heroes - but these are the real heroes."

On Friday, Manchester City boss Enzo Maresca refused to discuss Grealish's actions at Everton, but did praise his character.

Maresca said: "It's not correct to talk about Jack in this moment, first of all because he is an Everton player and secondly because I don't have all the information.

"I still think he is a good guy and has a big heart."

In April, Grealish extended his role as principal ambassador to Special Olympics Great Britain for a further three years, having first joined in 2022.

Grealish marked the occasion by hosting five of the 10 Special Olympics GB athletes who completed the London Marathon at Everton's Hill Dickinson Stadium, surprising the athletes with a VIP experience, a stadium tour and spending time with them pitchside.

Those at Everton also regard Grealish as one of the first to engage with their community programme at Finch Farm, as well as meeting with the Everton in the Community Down Syndrome team.

Grealish often talks about the inspiration he takes from his sister Hollie, who has cerebral palsy.

He has, however, hit the headlines in less welcome circumstances over the years, and this latest incident ushered in more.

In April, Grealish was pictured asleep at a Manchester rooftop bar surrounded by drinks. It was a scene that is certainly not against the law but was at best unwise, especially with ever-present phone cameras around and the fact he was in rehabilitation from injury.

In March 2020, he was fined by his club Aston Villa and apologised publicly after breaking lockdown guidelines during the pandemic after leaving his house to visit a friend.

In November 2020, he admitted two counts of careless driving relating to two incidents in which a Citroen van and a Mercedes were damaged.

And yet, speak to most people in football - certainly at Everton - and the character references are unfailingly glowing about his outgoing personality and kind-hearted gestures, making his breach of discipline even more painful for his many admirers.

But after this latest setback, Grealish is running out of time and opportunities to justify that continued support.