Truman and Jacobson opened their store in late-November 1919, and their goal was to make it a first-class operation. The business partners were making money, and they were in step with the times in terms of fashion, since most Americans wanted "Normalcy" in 1920. However, by 1921, the silk shirt that had sold very well was no longer in demand, and by the Summer of 1921, people entered Truman and Jacobson, but they didn't buy much, and the parners borrowed to keep the latest styles on the shelves . . . both men knew that their prosperity was most likely at an end.
Meanwhile, Truman volunteered to help plan-and-run the American Legion convention in Kansas City which was scheduled for the Fall of 1921. On 1 November 1921, the "Who's Who" of World War I appeared, including Marshal Ferdinand Foch, John J. Pershing, Eddie Rickenbacker, as well as Vice-President Calvin Coolidge. Truman had the honor of presenting flags to the Allied commanders, Pershing and Foch.
Truman and Jacobson failed in 1922, and both men decided to pay off their creditors ($35k) instead of declaring bankruptcy (however Jacobson would declare himself bankrupt three years later). As a result, Truman was strapped for money for the next 20 years. The store had been a colossal failure, but few thought it was Truman's fault, in that he (like many others) was a victim of circumstances beyond his control. Truman blamed the Republicans in Washington, D.C., especially the tight-money policies of SecTreas Andrew Mellon. Truman conveniently overlooked (or ignored) that before leaving office, President Wilson cut government spending and raised taxes.
Tom Pendergast would become a "Boss" in the truest sense; he was very intelligent, jaunty at heart, but looked menacing . . . he was both formidable and engaging. Pendergast saw politics as a way to bring in money and to increase influence, in a way that "Alderman Jim" never envisioned. Pendergast expanded the saloon and wholesale liquor business, and soon was able to control the flow of liquor to other saloons, which meant more influence/power. Also, Pendergast started the Ready-Mixed Concrete Company, which was the first in the area to manufacture ready-mixed concrete at the factory, which was delivered by truck to construction sites.
Other Pendergast companies soon appeared in construction, paving, painting, pipelines, and even cigars, and tremendous amounts of money and influence followed. Pendergast focused on satisfying the needs of as many people as possible to increase his power base. Pendergast largely kept to himself, which added to his mystique; eventually, Truman would be part of the Pendergast organization, and would, much like Pendergast, learn much about politics.
But in the 1920s, Pendergast's growing power had limits, largely because he had rivals in Kansas City. Pendergast could play rough against his rivals, using tactics made famous by
Boss Tweed in New York City in the late-1800s, and "stealing" elections became a fine art. Pendergast's brother, Mike, was the "enforcer", as well as being responsible for increasing the "Country Vote", which included Independence, Missouri. Mike had a daughter and six sons, with the oldest being Jim Pendergast, whom Truman came to know and admire during the Great War. With Pendergast having daughters but no son, Jim was the heir apparent to the Pendergast organization.
During the late-Fall/early-Winter of 1921, Jim Pendergast brought his father, Mike, to Truman and Jacobson in order for his father to meet Truman. By then, Truman knew his haberdashery was going to fail (as did Jim), and Jim and Mike wanted to know if Truman was interested in running for the office of Eastern Judge of Jackson County. The elected office was a job in the courthouse in Independence, which was the equivalent of being a county commissioner, a prime political post that the Pendergast Machine would love to have, and to keep.
The idea of approaching Truman was Jim's alone, but Mike was ready to embrace Truman due to Jim's description of Truman's character . . . if Captain Truman was okay for Jim, he was okay for Mike. Truman accepted their offer at once without any hesitation. To Jim and Mike, Truman was their dream candidate, and as subsequent years proved, Truman offered far more to the Pendergast Machine than the machine offered Truman. For Truman, the timing of the offer was perfect, in that he did indeed need to be rescued. If elected, Truman would serve a term of two years; if Truman hadn't been recruited by Jim and Mike Pendergast, he probably would have never entered politics.
On 8 March 1922, Truman (age 38) announced his candidacy for the position of Eastern Judge. Truman was the American Legion candidate, within the umbrella of the Democratic Party in the county. Four other Democrats were in the race for the nomination as well, and all were formidable opponents. Truman's platform centered around sound roads and management of county business, but Truman had to learn how to give speeches well enough to communicate his political goals.
The main event for the Democratic candidates occurred at a political picnic in July 1922, where over 4000 showed up, twice the normal crowd. Truman was flown in as an attention-getting move, and after throwing up behind the scenes (it was his first flight), Truman recovered to give his speech, which was scheduled last. By then, Truman was a far-better public speaker, able to effectively state the problem and then his proposed solution(s). One of the main points of Truman's speech was that he wanted the county to stop operating in perpetual debt; after his impassioned speech, it seemed to be a foregone conclusion that Truman would win the Democratic primary.
Truman won the primary, but privately he was disappointed in the efforts put forth by the Pendergast Machine on his behalf, in that he expected far more money/support. The main reason for Truman's disappointment was that he won in a nail-biter, winning by only 279 votes out of 11,000+ cast. And that margin was due to armed backup by those in support of Truman that blocked violent shenanigans from Pendergast's rivals in Kansas City and the surrounding areas. Those that came to Truman's rescue with guns at the polls were largely men that were under his command in Battery D in the 129th Field Artillery during World War I.
For the Democrats on the national stage, it was a rough time in 1924; it took a record 103 ballots to nominate their candidate during the convention, selecting John W. Davis who was destined to lose. An effort to nominate Al Smith (the party's candidate in 1928) failed, along with a resolution on the platform to denounce the KKK. When William Jennings Bryan tried to speak, he was rudely shouted down by unruly delegates on the floor. The only positive moment during the convention was the nomination speech for Al Smith, delivered by FDR. Tom Pendergast was at the convention, and he was spellbound by FDR.
Truman ran for Eastern Judge again in 1924, and this time he won the Democratic primary by a little over 1000 votes. The Kansas City Star put aside its distaste for Pendergast and focused on the good works and sound management by Truman. Shockingly, the Republican candidate prevailed in the general election, due in large part to substantial support from the Ku Klux Klan.
Truman served two full terms as presiding judge from January 1927 to December 1934, and he was acclaimed by nearly all for doing a great job in office. In essence, Truman was the CEO of Jackson County, and in many ways, as the topmost elected official, he was the county's de facto President. Truman even raised funds so the Republican Party could hold their national convention in Kansas City, since they were about to pull out due to costs; Truman stated that it would be good for the economy of Kansas City to host the Republican convention in the land of the Democrats. Truman had even more power to improve roads, doing so with concrete, which was readily available from Ready-Mixed Concrete, one of Pendergast's many companies.