Churchill spent most of his life swimming in a mountain of personal debt
Gambled equivalent of £40,000 a year on holidays to the south of France
Had £54,000 bill from his wine merchant, including £16,000 for Champagne
Secret benefactor gave him £1million in 1940 as he became Prime Minister
When the underwriters protested that he was still able to earn money from journalism, his broker retorted that he could not physically write — the article had been dictated to a secretary. Mere talking, he insisted, should not be classed as work. The insurers paid up.
Such sharp practice was not confined to his insurance claims. He told the Inland Revenue he had retired as an author, which entitled him to defer a large income tax bill.
To avoid paying tax on book royalties, he sold the rights and successfully argued that the money he received was not income but capital gains, which at the time was exempt from tax.
He borrowed money from his children’s trusts, and even cut down his drinking — not to curb his expenses, but to win a bet with the press baron Lord Rothermere, who wagered him £600 that Churchill would not drink any brandy or undiluted spirits for a whole year.
Churchill took the bet, reasoning to Clemmie that money won gambling was not subject to tax. But he turned down a bigger bet, £2,000 [£100,000], that he could not remain teetotal for 12 months.
‘I refused,’ he explained, ‘as I think life would not be worth living.’
In fact, his accumulated bills for alcohol came to £900 (£54,000). His gambling was even more costly — 66,000 francs (about £50,000) in a single holiday at a casino in Cannes in 1936, for example.