Kansas City’s Boss Pendergast Pleads Guilty to Income Tax Evasion Summary

  • Last updated on November 11, 2022

Thomas Joseph Pendergast, head of a Democratic political machine that dominated politics in Kansas City, Missouri, for more than thirty years, pleaded guilty to charges of income tax evasion and spent fifteen months in federal prison. After his conviction, his political machine never regained its former power and influence. Harry S. Truman, later a U.S. senator, vice president, and president, was associated with Pendergast in his early political career.

Summary of Event

The Pendergast political machine dominated politics and municipal government in Kansas City, Missouri, and surrounding Jackson County from the 1890’s through the 1930’s. The Democratic machine was founded by James Pendergast, who owned a saloon-restaurant that doubled as a boarding house in a working-class area in the West Bottoms area of the city. Pendergast was elected to the city’s board of aldermen in 1892. Eventually, his influence was great enough that other politicians sought his backing. By 1900 the Pendergast machine was powerful enough to get its own candidate, James A. Reed, elected mayor of Kansas City. Pendergast, Thomas Joseph Truman, Harry S. [p]Truman, Harry S.;and Thomas Joseph Pendergast[Pendergast] Tax evasion;Tom Pendergast[Pendergast] [kw]Pendergast Pleads Guilty to Income Tax Evasion, Kansas City’s Boss (May 22, 1939) [kw]Tax Evasion, Kansas City’s Boss Pendergast Pleads Guilty to Income (May 22, 1939) Pendergast, Thomas Joseph Truman, Harry S. [p]Truman, Harry S.;and Thomas Joseph Pendergast[Pendergast] Tax evasion;Tom Pendergast[Pendergast] [g]United States;May 22, 1939: Kansas City’s Boss Pendergast Pleads Guilty to Income Tax Evasion[00660] [c]Corruption;May 22, 1939: Kansas City’s Boss Pendergast Pleads Guilty to Income Tax Evasion[00660] [c]Gambling;May 22, 1939: Kansas City’s Boss Pendergast Pleads Guilty to Income Tax Evasion[00660] [c]Organized crime and racketeering;May 22, 1939: Kansas City’s Boss Pendergast Pleads Guilty to Income Tax Evasion[00660] [c]Politics;May 22, 1939: Kansas City’s Boss Pendergast Pleads Guilty to Income Tax Evasion[00660] Pendergast, James

After Pendergast retired from politics in 1910, his brother, Thomas Joseph Pendergast, was elected to the board of aldermen and became the head of the machine. The Pendergast machine reached its greatest height under “Boss Tom’s” leadership. The machine controlled hiring for city jobs, the awarding of city contracts, and elections to many city and Jackson County government positions. Kickbacks from city and county employees and contractors doing business with the city funded the machine’s social welfare activities, which sought to influence voters by providing for the needs of the poor or those facing health concerns, job loss, or other problems. During the mid- and late 1930’s, federal investigations into extensive voter fraud and Thomas Pendergast’s evasion of income taxes led to the decline and ultimate demise of the Pendergast machine.

During the early 1930’s, Thomas Pendergast’s political machine was at the height of its powers. Pendergast not only controlled politics and government in Kansas City and Jackson County but also ensured his candidate, Harry S. Truman, was elected as U.S. senator in 1934. The incumbent governor of Missouri, Lloyd C. Stark, also owed his 1936 election to a great extent to Pendergast’s support. Additionally, President Franklin D. Roosevelt’s administration funneled much of the funds for New Deal relief and public works programs through Pendergast’s machine, giving him even more jobs and funds to hand out to patrons.

During the mid- and late 1930’s, the Pendergast dynasty began to deteriorate. For decades, the machine had controlled Kansas City and Jackson County elections with remarkable efficiency. During the late 1920’s, as the number of Republican votes in the metropolitan area began to grow, the Democratic machine added sixty thousand nonexistent or long-dead voters to the voting rolls. On election days, operatives paid by the machine voted under these names, often voting several times in various precincts and receiving twenty-five cents per vote. City elections in 1936 were accompanied by so much open violence, voter intimidation, and voter fraud that there were calls for a federal investigation. Milligan, Maurice M. Maurice M. Milligan, the federal district attorney in Kansas City, began an investigation into the voter fraud allegations in 1937.

As a result of investigations over the next two years, more than two hundred fifty operatives of the Pendergast machine were convicted of voter fraud and more than two hundred of those convicted spent time in jail. Initially, the machine showed little concern for these investigations. Demonstrating open contempt for the legal proceedings, the machine paid the fines of those who had been convicted and even paid salaries to those who were imprisoned, with the funds for this coming from a special assessment made on the gambling interests the machine controlled. The investigations and litigation associated with the voter fraud cases began to turn public opinion against the machine.

Truman, in the Senate by this point, tried to use his senatorial privileges to block the reappointment of Milligan as federal prosecutor in Kansas City. Truman attacked Milligan in a speech on the Senate floor in February, 1938. In this speech, he also attacked federal district judges Merrill E. Otis and Albert L. Reeves. Truman alleged that these judges, who had been appointed by Republican presidents Harding, Warren G. Warren G. Harding and Coolidge, Calvin Calvin Coolidge, were the most “violently partisan” judges since the days of the Federalist appointees that troubled Jefferson, Thomas Thomas Jefferson. Truman claimed that Milligan and these judges were out to get Democrats. “A Jackson County Democrat has as much chance of a fair trial in the Federal District Court [in Kansas City] as a Jew would in a Hitler Court or a Trotsky follower before Stalin,” Truman suggested. Ultimately, however, President Roosevelt, Franklin D. Roosevelt insisted that Milligan be retained, and Truman backed down, allowing a voice vote in the Senate to approve the reappointment.

In addition to the voter fraud issue, the Bureau of Internal Revenue;and Tom Pendergast[Pendergast] Bureau of Internal Revenue (now the Internal Revenue Service, or IRS) began an investigation of Pendergast’s personal finances in 1938. There had long been rumors that Pendergast received payoffs, handled by members of organized crime families, from businesses involved in illegal gambling, liquor, and prostitution. Investigators also heard rumors that Pendergast had received a large payoff for helping to broker a compromise on insurance-rate rebates that saved several large insurance companies millions of dollars. Investigators found that Pendergast had received about $750,000 for this influence peddling, although much of that money was passed on to others as payoffs for their role in the compromise. Federal investigators also knew that Pendergast gambled heavily on horse Horse racing races and apparently had ready access to large amounts of cash to pay his sizable gambling debts. Eventually, the investigation led to charges that Pendergast had failed to report approximately $1.24 million in income over the previous decade. He was arraigned, and pleaded not guilty, on May 1 to two counts of income tax evasion.

Ever a realist, Pendergast knew the case against him was very strong and changed his plea to guilty on May 22. Judge Otis presided over this case and sentenced Pendergast to fifteen months in prison on the first count. On the second count, Pendergast received a three-year prison sentence and a $10,000 fine. Otis, however, suspended the prison sentence on this count and substituted five years probation. Additionally, Pendergast was ordered to pay $430,000 in back taxes and penalties and was forbidden to participate in any political activity unless his “full civil rights” were restored by a presidential pardon. Other people associated with Pendergast’s machine also were convicted of income tax evasion. In the two years preceding his conviction, Pendergast had suffered a heart attack and undergone three abdominal surgeries; Otis said that he had taken Pendergast’s poor health into consideration in determining the sentence. The sentences were met with public condemnation.

Pendergast died on January 26, 1945. Truman, who just days earlier had been inaugurated as vice president under Roosevelt, attended Pendergast’s funeral against the advice of many who counseled him not to remind the public of his earlier ties to a corrupt political machine. Truman stated that Pendergast had “always been my friend and I was his.” Truman, however, always contended that Pendergast had never exercised undue influence on his own actions in the Senate.


Although the Pendergast machine continued to have some influence for a few years, it never recovered its power after the voter fraud convictions and Pendergast’s conviction for income tax evasion. Many Pendergast appointees resigned or were forced from office in the following months. An investigation disclosed approximately three thousand people on the city payroll who had been hired by the machine but apparently did no work for their pay. In 1940, a political-machine-fighting coalition, the Citizen’s Reform ticket, won most of the seats in the city election. Candidates backed by Pendergast’s machine, however, still won in five of the city’s sixteen wards.

Pendergast’s friends and associates largely abandoned him after his release from prison, and his last years were spent in lonely isolation. Politics had been Pendergast’s life, and being barred from participation in the political process was an especially bitter part of his punishment. Pendergast hoped that he would receive a pardon from President Roosevelt, Franklin D. Roosevelt, but the pardon never came. Pendergast, Thomas Joseph Truman, Harry S. [p]Truman, Harry S.;and Thomas Joseph Pendergast[Pendergast] Tax evasion;Tom Pendergast[Pendergast]

Further Reading
  • citation-type="booksimple"

    xlink:type="simple">Dorsett, Lyle W. The Pendergast Machine. New York: Oxford University Press, 1968. An early work, still valuable as a general history of the Pendergast machine and its influence on Kansas City politics.
  • citation-type="booksimple"

    xlink:type="simple">Farrell, Robert H. Truman and Pendergast. Columbia: University of Missouri Press, 1999. Examines the working relationship between Pendergast and Harry S. Truman in the days before Truman became U.S. president.
  • citation-type="booksimple"

    xlink:type="simple">Hartmann, Rudolph H. The Kansas City Investigation: Pendergast’s Downfall, 1938-1939. Edited by Robert H. Ferrell. Columbia: University of Missouri Press, 1999. Based on the official 1942 report of the Pendergast income tax evasion investigation by a Treasury Department agent. An account of the inner workings of the case that also reveals a history of the machine era in American politics.
  • citation-type="booksimple"

    xlink:type="simple">Larsen, Lawrence H., and Nancy J. Hulston. Pendergast! Columbia: University of Missouri Press, 1997. Using prison records and previously unavailable family records, Larsen and Hulston present the first full-scale biography of Pendergast.
  • citation-type="booksimple"

    xlink:type="simple">Milligan, Maurice M. Missouri Waltz: The Inside Story of the Pendergast Machine by the Man Who Smashed It. New York: C. Scribner’s Sons, 1948. The inside story of the case against Pendergast by the federal prosecutor who brought the political boss to justice.

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Categories: History