He lavished more than £3 million on close members of his family, including a £750,000 gift to his ex-wife Hazel.
This was inevitably followed by the luxury houses, a villa in Spain, a fleet of supercars, globetrotting holidays and of course jewellery for his wife.
Unfortunately for Mr McGuinness,44, he couldn't resist the opportunity to indulge in his greatest passion...football.
While he could afford fast cars and foreign holidays, bankrolling a football club put him in a different league altogether.
Now, thanks largely to a disastrous £4 million investment in lowly Scottish side Livingston FC, Mr McGuinness is more than £2 million in debt and is set to have his house repossessed by a bank.
The Royal Bank of Scotland last month won a court order to take possession of his £500,000 family home and he has reportedly been declared bankrupt over a £35,000 debt owed for a Porsche sports car that has now been repossessed.
He is likely to be evicted following an appeal hearing in four weeks time and meanwhile he is staying out of sight behind the gates of the converted schoolhouse in Larkhall, Lanarkshire, and refusing to comment on his downfall.
Not surprisingly, he and his loyal wife Sandra, 39, are understood to be deeply upset by this turn of events.
And to make matters worse Sandra's parents, who live in a small house on the site, are set to be made homeless too.
He and his wife are preparing to go back to work something that was unthinkable just over a decade ago when they had the world at their feet.
Sandra, a former nurse, is said to have enrolled on a hairdressing course in the hope of starting a new career and the couple are even applying for a council house.
A friend said: "John has been decimated by what has happened. In no time at all, he's gone from millionaire to someone who's had his car repossessed.
"Sandra has an appointment with the local housing office to see if they can come up with a council house. People might not like to think of John deserving a subsidised home but his needs are as great as any other homeless person."
The extraordinary 'rags to riches to rags' story began in January 1997 when Mr McGuinness hit the £10m jackpot while earning £150 a week and sleeping on his parents floor.
He swapped his battered-old Vauxhall Astra for a £140,000 Ferrari Modena Spyder. Others followed and at one point he had six in the drive, including a Bentley Arnage T Black Label and various Mercedes, Jaguars and BMW¹s.
He snapped up a £500,000 seafront apartment in Majorca, went on Caribbean cruises, five-star ski trips and holidays around the world.
He also spent £200,000 on his lavish wedding to Sandra in 2003.
But the invitation to join the board of second division Livingston FC proved to be his downfall. The Celtic fan and football-lover couldn't resist the glamour of helping to run his own club.
He helped Livingston reach the Scottish Premier League and win the league cup in 2004. However, success on the field was not mirrored in the club's finances and it crashed into administration.
Mr McGuinness had used his personal fortune to guarantee club loans and they were called in. Legal battles ensued, which Mr McGuinness ultimately lost and his millions disappeared.
With huge legal costs adding to his debts, the former multi-millionaire owes £2.1m to the Royal Bank of Scotland and is said to have no money left to pay the bank with. Even his house will only pay off a fraction of the debts.
His cars have had to go and expensive jewellery, including a Rolex watch, have been sold at cutprice rates in a bid to raise cash.
Commenting on his disastrous football investment three years ago, he said: "I probably was a bit naïve and perhaps made a mistake but I got involved with the best possible intentions.
"I just want my life to get back to the way it was before but minus the football.
"People see me and see a really quiet chap who might help people out. But I have learned a great deal from the experience, which I suppose is a positive thing to take out of it."
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