Lough points out that Churchill’s switchback from the Tories, to the Liberals, and back to the Tories can be situated in terms of his personal finances. Having started out in the party of the landed interest, he switched to the party of the entrepreneur and the professional when he started to earn serious money with his writing. Having finally acquired land, he switched back to the Tories.
.. this was a guy who decided to drink champagne only five times a week in order to save money.
.. In fact, he tried all the ways rich men find to lose money, except yachting and mistresses.
.. Money also illuminates his inner life. The Black Dog struck in 1937-8, when he was savaged by margin calls in the hundreds of thousands of pounds on his appallingly ill-thought-out share portfolio, pursued by the Inland Revenue, enormously overdrawn at his bank, writing 2000 words a day or more for fear that his publisher would reclaim the long-spent advance on Marlborough: His Life and Times. Of course he was depressed.
.. In the end, one important lesson from this book is that perhaps standards of public integrity and financial probity have actually improved.
In 1923, Churchill accepted a £250,000 fee to lobby on behalf of Shell Oil. He used this money to underwrite part of a major bond issue by Daily Mail & General Trust, a newspaper that also published him and an obvious source of political influence, in exchange for a 2% commission. Vickers, Da Costa called in a favour with DM>’s merchant bank to hold a chunk of the business back for him, after Churchill had Shell send the cheque to his brother Jack’s home address for secrecy’s sake. Jack, of course, had just made partner at Vickers, Da Costa, no doubt in part because he brought Winston’s account with him from Grenfell’s and it wasn’t yet obvious what a mess he was going to be. Churchill collected on the transaction, went to stay with the Duke of Westminster in Mimizan, and proceeded to lose the lot at the casino in Biarritz.
I doubt you’d get away with that now.