“Lucian once told me that in the 1960s, a decade when his work was out of fashion and hard to sell, gambling helped him,” Freud biographer Martin Gayford wrote
in an article for The Spectator
in 2013. “Did he mean it helped him to make money? No, he answered, it helped him not to care too much about money.” Though Freud claimed not to care about his finances and seemed unconcerned about whether his paintings sold, he never had too much to worry about—by his late twenties, he’d already
earned art world respect.
Freud liked both winning and losing—no matter the outcome, the noted workhorse could always go home to paint (he maintained his practice until he died, in 2011, at age 88). When he became more successful, and his art-making itself was less of a gamble, he curtailed his horse-betting, as well.
If Freud’s relationship with McLean was cordial, he maintained a more tense friendship with the thuggish Kray twins, Ronnie and Reggie. The pair owned nightclubs, set off fire bombs, conducted robberies and a few murders, partnered with the American mafia, and supplied Frank Sinatra with bodyguards.
Freud amassed £500,000 worth of debt to the brothers’ gambling outfit. Once, they threatened to cut his hand off unless he produced £1,000 for them. In that case, Lord Jacob Rothschild came to his rescue
—throughout his life, Freud relied on his wealthier friends and patrons (in his lifetime, Freud also painted the likes of Kate Moss and Queen Elizabeth II) to settle his troubles with his less refined acquaintances.
In Jumpin’ Jack Flash: David Litvinoff and the Rock‘n’Roll Underworld (2016), writer Keiron Pim suggests that Freud may even have ordered the Kray twins to brutalize David Litvinoff, a gossip columnist-turned-film consultant. In a twist worthy of Hollywood, the pair met when Freud discovered that Litvinoff, who resembled the painter, had been impersonating him in bars to put his drinks on Freud’s tab.