Why Winston Churchill Was So Bad With Money

The British prime minister could handle the Blitz but not his bills.

Sir Winston Churchill departs 10 Downing Street with his poodle. (Associated Press)

In May of 1940, as French forces crumpled in the face of the Nazi onslaught and the British anxiously scanned the skies for signs of the dreaded invasion, the newly installed prime minister was preoccupied with another pressing problem. Where would he get the money to pay his bill from the shirtmaker? Britain’s predicament was dire, but so was Winston Churchill’s. He owed not just the shirtmaker, but the watchmaker, the wine merchants, and the printers as well. He was overdrawn at the bank, he owed interest payments on his debts, his taxes were conspicuously late, and his publishers were clamoring for an overdue book on which he had taken a large advance. Churchill would lead Britain through the Blitz a few months later, but first he needed money.

Winston Churchill’s finances were a shambles for most of his life. It was a state of affairs, as David Lough reveals in No More Champagne: Churchill and His Money, entirely of Churchill’s own making. Over the course of a tumultuous political career spanning more than half a century and encompassing two changes of party and a dozen cabinet positions, including two stints as prime minister, Churchill spent money he did not have—extravagantly.

He took lavish trips to sun himself in the Bahamas and to yacht in the Mediterranean and to shoot in Normandy. He bought cases of champagne and boxes of cigars, costly pink-silk underclothes, and a succession of rickety houses. He embarked on prodigal rebuilding projects that nearly proved his ruin. Churchill, a friend reportedly remarked, was “easily satisfied with the best.” He gambled his way across Monte Carlo and Biarritz, and, in a bid to right his capsized finances, speculated in stocks just as the American market reached its vertiginous Jazz Age heights. For Churchill personally, out of office for most of the 1930s, Britain’s declaration of war on Germany in September of 1939 came as a kind of perverse relief. He had been a vehement critic of the government’s policy of appeasement, and now—his assessment of Hitler vindicated—he could return, finally, to the seat of power. For a man who had teetered on the brink of bankruptcy in the 1930s, in debt to the tune of as much as $3.75 million in today’s money, a place in the cabinet also bought him precious time with his creditors. Eventually the government would even pick up a portion of his liquor bill.

Churchill bought fine shirts and boxes of cigars—and pink-silk underclothes—that he couldn’t afford. (Ullstein Bild / Getty)

The money troubles—and solutions—that preoccupied Churchill, an aristocrat who cut his political teeth in a plutocratic age, make for spicy reading in our own increasingly plutocratic times. Throughout his political career, he relied upon rich acquaintances to bail him out. After he lost his seat in Parliament in 1922, he engaged in dubious lobbying on behalf of oil companies. He stretched all available loopholes to avoid paying taxes, even (and especially) when he served as chancellor of the Exchequer, the head of Great Britain’s Treasury, from 1924 to 1929. And in the end, he made his fortune by taking advantage of papers commandeered from government files to construct his blockbuster memoirs.

Such chicanery is distressingly familiar these days, but it is also different. As Lough points out, Churchill’s conduct would hardly have met “the standards of transparency expected of today’s politicians.” Some of Churchill’s financial bounty came in the unlaundered (or lightly laundered) form of direct gifts and loans. Take the 1940 crisis when the shirtmaker presented his bill. The prime minister was saved by a discreet payment amounting to nearly $375,000 in today’s money, from a foreign-born financier, conveyed in a check written to someone else and endorsed over to Churchill.

Haberdashery subsidies may seem both quaint and crude in the era of mega-donors and super PACs. And yet one basic question remains the same. What do you get in return when you furnish a library in a politician’s house, as one of Churchill’s friends did when he was a junior government minister? Or when you pay a former secretary of state and likely presidential contender hundreds of thousands of dollars to give a canned speech? Churchill’s example suggests that in such situations, just who is the player—and who is being played—can be a trickier matter than it may first seem.

For a man spending money he didn’t have, Churchill had one big advantage. Most people assumed, given his flagrant style, that he was rich. In truth, he wasn’t born to a great fortune, nor did he marry into one. Churchill’s father, Randolph, was a younger son, and the family’s Blenheim estate was in any case seriously reduced. Churchill’s American mother, Jennie, was no Downton Abbey–style heiress but a spendthrift outfitted with a smaller-than-advertised dowry. When Jennie married a second time, in 1900, after Lord Randolph’s death, her new husband obligingly took a stack of her unpaid bills to deal with on their honeymoon, but objected that it was “a bit thick” that he was expected to pay for the carriage his predecessor had purchased in the 1880s. Though Churchill’s family talked of him marrying an heiress, when he finally did wed, at the age of 33, it was for love. His wife, Clementine, was well born but poverty stricken; before her marriage she worked as a seamstress and taught French to earn her keep.

Neither the army (Churchill’s first career) nor politics could come close to satisfying his need for money. In an era before Goldman Sachs and General Mills were willing to pay munificently for a politician’s speechifying, only by writing did Churchill have a shot at staying afloat. In 1930, Churchill pumped out more than 40 articles and in addition pledged to his publishers that he would finish three books posthaste. Hit by a car in New York City the following year, he cabled his agent that he could “produce literary gem about 2,400 words” about the accident. Churchill had to turn every thought, every experience, into words and cash, an imperative that, as the historian Jonathan Rose has recently argued, only exaggerated his propensity to cast himself as a hero on the world stage.

Had the Churchills made their home in a more modest dwelling, as Clementine apparently wanted, rather than the money pit Chartwell (which Winston purchased on the sly when she was laid up after the birth of their fifth child), his income would have been sufficient to maintain the family in style. But as a wage earner who kept company with rentiers, Churchill insisted on grandeur. Bespoke shirts, oyster-and-pheasant dinners, and nights in Monte Carlo casinos required him to find less middle-class ways of raising cash.

The most controversial of Churchill’s associations, both at the time and since, was with bankers and businessmen of Jewish origin, among them Sir Ernest Cassel and Sir Henry Strakosch. Early in Churchill’s career, Cassel paid to furnish the library in Churchill’s new house; after the First World War, he engaged in subterfuge to take a costly real-estate blunder off Churchill’s hands, claiming falsely that Churchill had acquired the property on his behalf. It was the Austrian-born Strakosch who kept Churchill from bankruptcy in 1938 and again in 1940, when the shirtmaker demanded his fee. The Nazis liked to claim that Churchill was in the pocket of Jewish financiers, a charge that the Holocaust denier David Irving has since contemptibly repeated. Lough, a banker himself, who doggedly pursues the ins and outs of Churchill’s finances in No More Champagne, argues that Strakosch sought nothing in return for his payments—and received nothing, save an invitation to membership in the dining society to which Churchill belonged. “There was no other reward.” Churchill’s out-of-office lobbying on behalf of a deal for the oil companies ultimately went nowhere too; as soon as he had the chance to get back into government, he ditched the assignment (but kept the money), and the deal fell apart. Nor did Churchill give special favors to Cassel, though as contemporary money-grubbing politicians discover, the appearance of impropriety can prove damaging on its own. During Churchill’s 1923 campaign for reelection to Parliament, socialists hectored him: “What about the 50,000 quid Cassel gave you?”


Positions can be bought or influenced, of course, but as in the case of Churchill, big money can also flow to a political figure simply because he or she is already backing the cause the donor supports. Strakosch was willing to help Churchill not because he saw a personal gain in the arrangement but because he thought him the only politician in Europe capable of standing up to Hitler. The bona fides of this transaction, though hardly an argument in favor of money in politics, do serve as a reminder that sometimes the suspicious financial smoke comes only from a cigar. Churchill was in any case too much of a loose cannon to be aimed. He was also too high-handed to view bailouts as anything but his due. And apart from the complaints of a few socialist agitators, his presumed wealth largely insulated him from the charges of corruption that dogged self-made politicians like his predecessor David Lloyd George.

Churchill started 1938 nearly bankrupt, but by the time he left office in 1945, he was a rich man. More than any political gift, it was a series of film deals that saved him, enabling him to pay back some of the money he owed Strakosch. Selling the film rights to his biography Marlborough: His Life and Times proved particularly lucrative; so did his arrangement with the producer and director Alexander Korda, who bought the rights to, of all things, A History of the English-Speaking Peoples. And the prospect of publishing his wartime memoirs was never far from the prime minister’s mind, not even as German bombs devastated British cities. Churchill instructed his private secretaries during the Blitz to gather up boxes of his official papers every month and mark them as “Personal Minutes.” (Even her worst enemies don’t accuse Hillary Clinton of a maneuver like that.)

After the war, he took 68 bundles of state papers home with him. To his successor, Clement Attlee, Churchill explained that he needed the documents to recount “the British war story.” “I am convinced,” he told Attlee’s emissary, “it would be to the advantage of our country to have it told, as perhaps I alone can tell it.” The old alchemy of turning experiences into words would at last yield blockbuster-size cash. Churchill’s Second World War set a global record for a nonfiction-publishing deal: $27.5 million in today’s money.