Truman and Bess got married in 1919. Their honeymoon took them through Chicago, Detroit, and Port Huron, Michigan. Soon afterward, Truman and his Jewish friend Eddie Jacobson opened Truman & Jacobson men’s clothing and accessories store in Kansas City. This venture was not Truman’s career aspiration, but he worked very hard. Unfortunately, for various reasons such as the economic environment, the business failed in 1922. Eddie declared bankruptcy unable to pay the debts, whereas Truman continued paying them off for almost two decades.

It was at this point that Truman began his political career. His army friend, Jim Pendergast was related to Alderman Jim Pendergast who played a key role in Kansas City Democratic politics. Pendergast was proudly Irish Catholic and served on the city council for 18 years. It was, however, his much younger brother Tom—TJ—who launched Truman’s political career. TJ exerted significant political influence by using a vast network of friends and associates.

With the blessing of the Pendergasts, Truman ran as a judge for Jackson County. The latter was an administrative, rather than judicial, position, not unlike a county commissioner. Truman launched the campaign in 1922 just before turning 38. He delivered speeches and promised, McCullough says, “better roads and a return to sound management of county business” (158).