There is a quote from Randolph Churchill, Winston's father, in which he scoffs at what he calls the American fear of debt. Winston himself apparently did not want to be guilty of that for there was almost never a time he did not have a maxed out overdraft and a long list of overdue bills to a variety of vendors. Even when he was earning more than a million pounds a year he was still triaging overdue bills, allowing the less persistent creditors to go unpaid for even years at a time.
If the spending habits of W. Churchill interest anybody, I found No More Champagne to be a fun/interesting read.