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• Alfie McLean was given paintings by Freud as payment for gambling debts
• When McLean died in 2006 he owned 23 paintings by the artist
• The pair were friends for four decades with the pair sharing a love for horse racing

By Adam Luck and Dominic Prince

PUBLISHED: 16:01 EST, 14 July 2012 | UPDATED: 19:21 EST, 14 July 2012

At time it might have seemed something of a gamble. But an unknown bookie ended up with a 100 million art collection after agreeing to be painted by artist Lucian Freud as payment for debts from betting.

When he died, Alfie McLean is said to have owned 23 Freud canvasses and several more by fellow artist and Soho denizen Francis Bacon – who had also become a close friend and client of the bookie through his  gambling habits.

Over a period of 40 years, Freud painted about 20 portraits of McLean and his family.

Favourite: The Lucian Freud painting is of Alfie McLean's two son's Sam and Paul which Mr McLean's wife Wilma lists as her favourite painting by the artist

Mr McLean began life as a trainer and small-time bookie on Northern Ireland's greyhound tracks and built up his businesses to include a chain of bookmakers' shops.

He first met Freud about 40 years ago at a racecourse after striking  up a conversation about vintage Bentley cars.

Freud – who died last year and left 96 million in his will – had a lifelong fascination with horses and soon opened an account with his new bookmaking friend and began to run up losses.

The first portraits of Mr McLean – known to Freud as 'The Big Man' – were painted in exchange for the bookie writing off gambling debts of just a few thousand pounds.

Alfie was discreet about his friendship with the great painter, except for giving one of his racehorses the cheeky name of Freud Bacon

But the two men's friendship seemed not to have been affected by their financial dealings – Freud was fascinated by Mr McLean and was often his guest at race meetings and sporting occasions such as Ulsterman Barry McGuigan's world title fights in the Eighties.

In return, McLean was discreet about his friendship with the great painter, except for giving one of his racehorses the cheeky name of Freud Bacon.

Mr McLean's widow, Wilma, said: 'My husband was very interested  in Lucian and his art. They became very good friends. I met Lucian three times in London. He never came over here. He was a nice man and painted my sons Sam and Paul.'

Freud preserved the sons' anonymity by simply calling the 2001 picture The Two Brothers From Ulster.

Mr McLean died aged 77 in 2006 and left 118 million in his will. But  it is not thought to contain the bulk of his extraordinary art collection, believed to be worth about 100 million, as he gave it to his children before his death.

Mrs McLean said: 'I do love art but I don't own the paintings any longer. 

'The collection is all gone. They all belong to the children now. That was what Alfie wanted and they would have inherited them anyway.

'I believe they are kept in safe storage now but I do not go into that. I do not really see the pictures. The collection is for the younger ones and I have not seen them in a few years. I gave them the pictures before my husband died.

'There were around 20 of them. I think my favourite one was with my husband and my eldest son Paul. Paul had his hand on Alfie's shoulder.

Unlikely muse: At the time it might have seemed something of a gamble. But Alfie McLean ended up with a 100million art collection after agreeing to be painted by artist Lucian Freud as payment for debts from betting

Popular: Artist Lucian Freud who ended up painting a total of 23 paintings for bookie Alfie McLean as payment for gambling debts

'It was painted in Lucian's studio about 30 years ago. He did not offer to paint me, which was a relief. I was hoping he wouldn't. Alfie quite enjoyed posing for the paintings. The two of them got on pretty well.'

Freud began painting his bookie after he signed up with New York art dealer William Acquavella in 1992 – and immediately confided in him that he had a problem.

Acquavella said: 'When I took him on, he said to me, “I've got a bookie – and I've got a bill with him.”

'So I had dinner with Alfie and I said, “Alfie, what does he owe you?” He says, “2.7 million.” I said,

“OK, thanks.” We had to work this out.'

The bookie's children all still live  in Ballymena, County Antrim, where Mr McLean was raised.

Sam and Paul, who runs the family bookmakers, live within yards of each other in comparatively modest homes – although Sam's generous driveway now boasts a brand new Maserati, a rare Mercedes sports car, a Mercedes SUV and another people carrier.

Their sister Catherine also lives in Ballymena, but in a flat close to the town centre.

A local source, who has met both Freud and Mr McLean but did not want to be named, said: 'I believe Alfie and Lucian Freud were both members of a Bentley owners' club and met at some outing in England a long time ago.

'Lucian, who was a fanatical gambler, then pricked up his ears when he realised this man was a bookmaker from Ballymena and started betting with McLean.'

A friend added: 'Freud ran up  massive debts, but apparently found Alfie McLean an irresistibly huge and ugly man.

'Freud painted people as he saw them, and that was not necessarily in a flattering light.

'Lucian introduced him to Francis Bacon, who was also a gambler.'