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Lucian Freud was a British painter who lived in Northern Ireland and died last year. He was a renowned painter but also a degenerate gambler.

Alfie McLean was a bookmaker in Northern Ireland. He met Lucian Freud 40 years ago at a racetrack. The two struck up a conversation about Bentley cars and became fast friends.

Over the ensuing four decades, Freud used McLean as his bookmaker. And he bet with him. He bet a lot. He bet so much that he racked up $4.2 million in debt to McLean.

Freud had to pay McLean in the only currency he had: his ability to paint. McLean let Freud paint portraits of him and his family as a way of paying off the gambling debts. In the end, McLean ended up with 23 of Freud’s paintings. Doesn’t sound like much, right?

Well, those 23 paintings are now worth a jaw-dropping $156 million.

Keep in mind, Alfie McLean operated a legal bookmaking shop. Freud, who was obsessed with horses, racked up millions of dollars in losses on racing with McLean, who extended his artist friend credit so he could keep betting.

From The Daily Mail:

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.’

And work it out they did. McLean, who was already worth more than $100 million by virtue of building a profitable and growing bookmaking operation, essentially doubled his net worth by letting his artist friend pay off his debts with paintings.

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