Winston Churchill was a huge party monster and racked up an absurd amount of debt
Churchill cut the estate's monthly expenses, which cost nearly $33,400 (£480) and included food, wages, maintenance, and cars, in half.
"Nothing expensive is to be bought, by either of us, without talking it over," Churchill wrote to this wife Clementine, according to Lough.
"No more champagne is to be bought. Unless special directions are given only white or red wine, or whisky and soda will be offered at luncheon, or dinner. The Wine Book to be shown to me every week. No more port is to be opened without special instructions."
"Cigars must be reduced to four a day. None should be put on the table; but only produced out of my case."
In addition to the proposed savings, the Churchills would "very rarely, if at all," invite guests over to the estate and would discontinue serving fish during dinner.
Within a year, Churchill's cost-saving plan unraveled and his family shipped off for a lengthy cruise around the Mediterranean.
While traveling, Churchill added a stop to Normandy to enjoy a wild pig-hunt with the duke of Westminister and the duke's new girlfriend Coco Chanel.
Churchill made a second detour to a nearby casino and gambled away $24,350 (£350).
Meanwhile, Churchill was still dodging bills from his architect Philip Tilden who was hired in 1923 to build a new wing to the Chartwell estate.
According to Lough, the Churchill's wanted "larger bedrooms, new bathrooms and kitchen, a library, a large study, and a room for entertaining."
At the time, Churchill had not approved Tilden's building cost estimates before work began on Chartwell. The swelling modernization costs soared, resulting in a series of allegations and delayed payments for Tilden.
"There were renewed threats of legal action on both sides, but the financial trail disappears at this point because Churchill's bank accounts for the last part of 1927 and 1928 are missing from his archive," Lough notes.
In 1927, the Chartwell estate and its furnishings are estimated to have cost at least $2,783,400 (£40,000), nearly triple Churchill's original estimate.
Churchill went on to become prime minster in 1940 and helped craft a successful Allied strategy against the Nazi's during World War II.
He was elected prime minister again in 1951, however, his financial woes shadowed the remainder of his life.