Lucian Freud's gamble: A portrait of the artist as a betting man

Before his work reached stratospheric value, he used to pay back his bookies with paintings. In an extract from his new book, Geordie Greig recounts conversations with the artist about money, a strange swap... and an elusive portrait of a gorilla

Lucian Freud, circa 1990 (David Montgomery/Getty Images)

Gambling was inherently linked to Lucian's painting. Whenever he made money from selling his pictures in the earlier part of his career, he gambled wildly, often losing the lot; yet when he began to make vast sums, he gave up gambling almost entirely. Risk fed his enjoyment of more risk, so when a financial safety net appeared as the price of his pictures soared, the relishing of gambling disappeared. When he had run up mountainous debts, death threats were made by unsavoury lenders. He would pay what was owed, when he could.

Lucian's art dealers grew used to him making agitated demands for cash. It was a constant cat-and-mouse game, with Lucian wanting more money and earlier, hopefully before a picture was finished, but at the latest on the day that the final brushstroke was applied. That said, it never made him rush to finish, as he kept a steely focus on achieving the best. Money mattered because as well as gambling, he needed it for his ex-girlfriends and children. He had their school fees to pay and would also get letters from some of his children at university about their monthly allowance. He was randomly generous when he could be, although some of the children found it embarrassing to be given a wedge of banknotes. And while his studio may have had a touch of squalor, he would offer guests the finest burgundy, and from there he ventured out to the best restaurants.

Like a financial Houdini, he believed that somehow he would always find an escape route, postponing, delaying, avoiding or at the last resort finding the wherewithal from others to pay. He had often lived off other people's money: his grandfather's legacy, odd cheques from his father, the margarine heir Peter Watson's generosity as a patron when he was a young man, also borrowing from the aristocratic heiress and art collector Jane Willoughby (one of Lucian's oldest friends, who was close to him for more than 50 years), and when really in dire straits selling her paintings that he owned, such as Francis Bacon's Two Figures. Although they became her property, they remained in his house. There was always a way out. But it was not always easy – twice Jane had to rescue the Bacon picture from pawnbrokers. It was amusing for her to look back on his recklessness with money, or rather her picture, but it was not so at the time.

One night in the 1970s when he lost £20,000 at the gambling mogul and conservationist John Aspinall's casino in Mayfair, pressure was immediately applied for him to pay the debt. In desperation, Lucian offered to paint a baby gorilla that Aspinall kept at his wildlife sanctuary in Kent. Laughing, Lucian recounted how John's mother-in-law, Dorothy Hastings, had brought a baby gorilla to his studio in the back of a black taxi, but not before it had urinated on her and ripped her dress. "My daughter Jane is on the cover of Tatler and here am I in the back of this cab with a wild animal out of control," she lamented. The animal portrait has never been seen.

Although betting at the racetrack was deleterious to his finances, he loved everything about the sport: the horses, the risk, the speed, the chase and the endeavour, as well as the company of jockeys, punters and bookies. He was addicted. "I always went all out. The idea of it being a sport seemed to me insane. The thing I liked was risking everything."

He never let his debts, which were often burdensome, unduly upset him, or affect his work. Gambling provided tension, which he loved. "There is nothing quite like gambling, the chance throw of the dice, as it were, that can leave you without a roof, or bring the thrill of winning," Lucian once said as a way of explaining his gambling habit. "It is like galloping or jumping through fire, sort of beyond what is sensible but it makes you feel alive."

Bookies inevitably became part of his life. He painted them, talked to them often, borrowed off them, sold them pictures and sometimes got blind drunk with them. Lucian's favourite bookmaker was Victor Chandler, who was debonair and mischievous, enjoyed a night out on the town and was besotted with Lucian. "I really did love him and would have done anything for him." He arranged for a daily to clean Lucian's flat, bought him shirts, had his clothes laundered, and even ordered special silk scarves from Sulka in New York that Lucian wanted. It was only over money that things became tricky. Collecting money from Lucian was a regular task for Chandler's associate, Michael Saunders. "Victor would say to me, 'He owes £50,000,' and we would say, 'Let's do a deal for £30,000.' There was no question of him not wanting to pay and somehow everything was settled in the end, but it was never easy getting the cash," Saunders said.

Saunders would walk up the 54 steps to the top floor of Lucian's studio before giving a coded secret knock on the outer front door to gain entry. There were often gifts brought to try to sweeten negotiations, and also because Chandler was naturally very generous. He arranged for a man called Jimmy the Cigar to fly to Warsaw to buy for Lucian the entire stock of Cuban cigars and Beluga caviar in the duty-free shop and then fly back the same day.

While Chandler, dapper, charming and amusing, was a public school boy, Saunders had started in the gambling industry at the age of 12, first as a street bet-taker. Both lived and breathed horses' form. "Lucian was a bookmaker's joy and nightmare. He never had any cash but that did not stop him from betting," Saunders said. "I loved him like a brother, and had many of the funniest times in my life with him," said Victor.

In 1983 Lucian was banned from most racetracks as a bad debtor but he was undeterred and used disguises to enter race meetings. "I remember laughing till I cried getting Lucian into one meet wearing a beanie hat, sunglasses and his grey cashmere coat. Somehow it worked," said Chandler. A chit from Chandler shows Lucian placing £400 on Man in the Middle and £80 on Grand Unit to win the 3.20pm. The sums were always multiples of eight, Lucian's lucky number. Chandler took the bet on tick and, as so often happened, Lucian lost. Chandler believes he liked the edge of losing as much as the delight of winning.

Over the years Lucian probably paid somewhere between £3m and £4m to the Millfield-educated bookie. "I'm going to have my betting shoes on today," Lucian would boast as he rang to back a horse, but they seldom brought him luck. Lucian did have some significant wins, but ultimately his addiction to risk meant he lost more than he won. Saunders would be sent to Clarke's, a favourite restaurant, just round the corner from his house, for a "debt breakfast" with Lucian. "I would know if he would pay on the day simply by what he did. If he put his glasses on, he would read the bill and that was hopeful. But if they stayed firmly on the table, Victor and I knew that he would take the bill home to read later. No money then," he said. Victor would sometimes try to make him more likely to pay by saying, "Lucian, please put your glasses on."

Chandler felt gambling was an intrinsic part of Lucian's character. "My impression is that he wasn't one for great self-analysis; he was almost animal. He went with his feelings, took what he wanted. That was his strength. You could also physically see it in his actions, eating with his fingers, tearing birds to pieces on his plate. When we cooked pheasant or partridge he wouldn't use a knife or fork. I don't think he ever articulated it, but the usual social rules that we apply to ourselves I don't think he ever thought they applied to him. There were no rules really."

In gambling and in painting (as well as in kick-starting endless new affairs) Lucian found an adrenalin rush. Both occupations, he thought, relied on a degree of chance with a tiny margin of error between success and failure. "I would see Lucian put his boot through a canvas when he felt it had gone wrong, when only the day before he had been convinced that it was going to work. It mirrored the hope of winning before a bet turns sour, the difference between winning and losing can be the head of a horse, and with a painting one fucked-up brushstroke," Chandler said.

It became a rite of passage for Lucian's bookies to sit for their portraits. It was the most practical way of reducing his debts, as they could buy his pictures at a discounted rate. Chandler liked sitting for Lucian as it gave him many hours of quiet time away from his hectic office. It immersed him in Lucian's world completely.

Lucian once told Andrew Parker Bowles how a few years earlier, Prince Charles – a keen "amateur" artist – sent a handwritten letter to him suggesting that he and Lucian exchange paintings. "It was such a cheek. It was almost like theft," said Lucian. "I never replied. What was there to say? It was embarrassing." Lucian was outraged, and when he crossly recounted this incident to the brigadier, Parker Bowles laughed. He saw the amusing side of a £3m work being swapped for one worth perhaps £5,000, painted by the man to whom he had lost his wife.

© Geordie Greig 2013. Extracted from 'Breakfast with Lucian' by Geordie Greig, published by Jonathan Cape, £25