Guffaws were let out across the country by those deeming the eyewatering fee - the highest ever for a defender - as money badly spent once more at Old Trafford. Then after a mixed first season came last summer's arrest following an incident on holiday in Mykonos.
He was given a suspended sentence of 21 months and 10 days in prison after being found guilty of repeated bodily harm, attempted bribery, violence against public employees and insult on the Greek island.
Harry Maguire will lead England's defence against Italy in the final of Euro 2020 on SundayInsurance Loans Mortgage Attorney Credit Lawyer
It comes just 324 days after he was arrested on the island of Mykonos while on holiday
He has lodged an official appeal against all three convictions but the hearing is likely to be postponed this year as the country's judicial system has stalled due to the coronavirus pandemic.
The England defender told the BBC soon after that plain-clothed police officers, who did not identify themselves, pulled over his group's minibus in Mykonos, threw him off the bus, hit him on his legs and told him his career was over.
The incident, however, threatened to make that last threat a reality, with his career - and his world, for that matter - appearing to to be in freefall.
All of that hard work to become the United captain and leader of England's defence was in danger of being in vain after being axed for a couple of internationals last autumn.
Yet now, 324 days after being arrested, that perceived risk of seeing his career fall by the wayside appears nothing more than a distant memory, with the 28-year-old set to figure once more at the heart of the England defence in the final of Euro 2020 against Italy at Wembley.
The spotlight has been on Maguire ever since his £80m move to Manchester United in 2019
Former United defender Rio Ferdinand insisted before the tournament began that Maguire's inclusion did not 'make sense' and was 'pointless' due to the fact he had not fully recovered from an ankle injury he had sustained playing for the Old Trafford side in early May.Insurance Loans Mortgage Attorney Credit Lawyer
But the ex-England centre-back - who has seen other predictions backfire at the tournament - was proved wrong by Maguire, who has returned to the side and is now indubitably the bedrock of Gareth Southgate's team.
Admittedly, that rock appeared on the verge of cracking in half when Maguire was sent off after just 31 minutes in the Nations League home defeat by Denmark in October in arguably one his worst performances for the national side.
It was the latest mistake in a poor run of form, which had also seen him heavily criticised for United's humiliating 6-1 defeat by Tottenham on home soil in the Premier League earlier that month.
He appeared uncomfortable playing in the three-at-the-back system used by Southgate and was caught out of position plenty of times as Christian Eriksen scored the winner later on in that fixture.
A few weeks after his Mykonos arrest, the England defender was sent off in a Nations League defeat by Denmark
Maguire spoke to a psychologist after struggling mentally after a nightmare summer
But his mistimed lunged on Kasper Dolberg, which resulted in his dismissal, appeared to suggest there were mental as well as physical issues to deal with following his Mykonos arrest.
'It was a challenging time but I am proud of the way I handled it and came through it,' Maguire said of the red card earlier this week.
'But four days before that game we had just beaten the No 1 ranked team in the world, Belgium, and I played 90 minutes and had a big part to play in that game.
'My touch was perhaps a bit off (against Denmark) – it was definitely off for the second booking I got.
'When I was walking off the pitch, of course I felt low. I felt like I was letting my team down. But mistakes happen and you bounce back and I am proud of the way I have handled myself from then on.
'It was important that I came back strong and performed well for Manchester United. I ended up scoring in a victory against Newcastle in our next match.'
Maguire revealed in May that he spoke to a psychologist after his nightmare summer, having opened up on the mental side of the game in an interview with Gary Neville on "'The Overlap' YouTube channel.
Maguire said: 'I think the stigma around it is wrong really, because when you play for a club like Manchester United it should be there for support.
'I think a lot of psychologists now aren't just psychologists, they're involved in the football club, you know the football side of it, you don't see someone going to see them and think "what problem has he got?".
'It could be a general chat about anything so I've obviously spoke to, we had one at England, Mitch, who I spoke to after my summer and the disappointment of the summer that I had. Yeah, I feel like they should be there and they should be part of the game.'
Jamie Carragher criticised Maguire for his performance against Everton but did reach out to him after the Mykonos incident
United and Maguire's form, however, appeared to improve after a mixed end to 2020 which saw them dumped out of the Champions League, yet the detractors continued to circle in their numbers in 2021, despite the club going on to finish runners-up to Manchester City in the league and reaching the Europa League final.
After conceding a last-minute equaliser in a 3-3 draw with Everton, Jamie Carragher accused Maguire of 'not being brave enough' and dropping too deep, making him unable