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Kansas City Crossroads Walking Tour
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Constructed in 1926, this building served as the headquarters of the Jackson County Democratic Club which was led by Thomas Joseph Pendergast, the penultimate "boss" of the infamous political machine that controlled Kansas City between 1926 and 1939. Referred to by many as "Boss Tom," Pendergast took over and expanded the political machine his brother built, choosing candidates for office who returned the favor by voting in line with the wishes of Boss Tom. As a result, Pendergast's businesses won prized city contracts and he wielded enormous influence over almost every aspect of Kansas City's political, economic, and cultural life.

As the Jackson County Democratic Party chair, Pendergast controlled the city's government through patronage, notably by providing jobs and government contracts in exchange for political support. Although Pendergast's corruption became well known by the 1930s, many residents continued to support Pendergast and his candidates because they believed his leadership had ameliorated many of the worst aspects of the Great Depression. Others appreciated Pendergast's refusal to enforce prohibition, leading to a vibrant jazz scene and Kansas City's reputation as a "Wide Open Town" where liquor and vice lived alongside strong financial support for civic institutions like schools and hospitals. Pendergast launched the political career of Harry S Truman, but his reign as a political boss ended in 1939 when he was convicted of income tax evasion

Today, the financial crimes and violence that occurred under Boss Tom's watch are sometimes overshadowed by nostalgia for the Jazz Age. and a perception that Pendergast and his men were supporters of integration. In reality, the advances for the Black Community had more to do with neighborhood leaders within the Pendergast orbit and the pragmatism of the political machine that traded funding for Black schools and hospitals for votes. At the same time, Kansas City was home to "Black-and-tan-clubs" that accepted all races than any American city beyond New York in an era otherwise dominated by segregation.


"Boss" Tom Pendergast

"Boss" Tom Pendergast

Thomas J. Pendergast Headquarters next to the Monroe Hotel

Window, Building, Brick, Urban design

Though political machines sometimes produced beneficial results for cities, they routinely came at the expense of corruption, heightened racial and ethnic tensions, and poorer civic services (because jobs went to people as political rewards instead of those best qualified). From the Civil War to the Great Depression, patronage machines ruled multiple large cities, including Kansas City. In addition to the Pendergast machine, famous political machines include those of William M. Tweed in New York, James M. Curley in Boston, and Richard J. Daley in Chicago.

The Pendergrast machine in Kansas City started with Thomas' brother, James, who built a political network with revenue from saloons, gambling, and brothels. Thomas' and James' parents, Michael and Mary Reidy Pendergast, immigrated to the U.S. from Tipperary, Ireland, to Ohio, and then moved to St. Joseph, Missouri, in 1859. Michael Pendergast enjoyed a longtime membership with the Teamsters, as did many of his children. James moved to Kansas City in 1876 at roughly twenty years old. James first worked as a laborer, working ten to twelve-hour shifts, six days a week. He took some of his wages and gambling winnings to purchase the American House in 1881, a saloon, boarding house, and hotel. The establishment sat in the West Bottoms neighborhood, known for its rampant drinking, gambling, and prostitution, a vice lifestyle Pendergast's American House helped foster. From 1884 to 1892, James opened a second saloon while also working his way up the local political ladder, from ward delegate to Alderman, learning how to turn favors into political influence along the way. 

In 1894, Thomas (the youngest of nine children) joined the family business in Kansas City, became a Teamster like his dad, and learned from Jim the ins and outs of grassroots politics. James served nine terms as an alderman on the city council before dying in 1911, ostensibly leaving the machine he built in the hands of his younger brother. After James' death, Thomas served as an alderman for a brief period before becoming chairman of the Jackson County Democratic Party. As head of the party machine, he exerted immense influence to win elections for hand-picked candidates and provided innumerable government jobs to political supporters. As Chairmen, he gained tremendous support from the working class because he successfully funneled millions of federal dollars to Kansas City during the Great Depression, and his patronage and leverage over the police allowed illegal gambling, prostitution, and liquor sales to thrive during Prohibition.

Where Jim would buy votes through favoritism in the form of jobs, food, and fuel, Tom manipulated elections. The Pendergast Machine consisted of an army of block captains, precinct captains and ward captains, for whom positions were political payments for favors done for the Machine. As a result, one Pendergast-appointed captain existed for every five voters. Additionally, Tom padded the voting ballots by using the names off the headstones of loyal yet dead democrats, known as the "ghost vote." By 1918, the Pendergast machine arranged for polling places to be staffed by election officials dedicated to Pendergast and guarded by thugs and ruffians. In one instance, Pendergast's Goat-Democratic-controlled police refused to intercede when a voter was beaten unconscious and bloodied during an election for the U.S. Congress involving Albert L. Reeves; Reeves suffered a resounding defeat.

Voter fraud was merely part of Boss Toms' political power and manipulation. Tom threatened to hand code and license violations to any First Ward saloon that refused to buy liquor from his newly created T. J. Pendergast Wholesale Liquor Company. In addition, Tom arranged for the Ross Construction Company, owned by one of his ward captains, Michael Ross, to acquire lucrative city and county road paving contracts. Pendergast also operated as a silent partner in the company that disposed of the city's garbage. Moreover, he benefitted by contributing to Kansas City's Ten Year Plan in 1930, which involved building downtown skyscrapers and several miles of city and county roads, mainly with Pendergast Ready-Mix concrete. Furthermore, Pendergast worked with his puppet city manager, Henry McElroy, to take federal funds obtained via the Works Progress Administration and use them to award financially rewarding contracts to and hire loyal city employees, who provided kickbacks to Pendergast's bookkeeper.

The historic headquarters played an integral role in the Pendergast machine. Tom Pendergast had the office constructed in the headquarters building, which could be accessed via a pathway to the second floor of his nextdoor Monroe Hotel. So, one could access the Jackson County Democratic Club in secret by entering the hotel instead of the headquarters building. But, not everyone arrived in secret. Pendergast held morning meetings three days a week with everyone from the unemployed and homeless to vendors and small-town politicians seeking favors. Pendergrast routinely paid for medical bills of those dealing with financial issues, provided aid to jobless citizens, or paid fines for those struggling. While on its face, the act seemed selfless, Pendergast said of providing help: "They vote for the fellow who gives it to them…We never ask them about their politics. We know pretty well how they will vote after we help them."

By the early 1930s, Pendergast controlled the police, and his machine reached as high as the state and federal governments. Much like a mob operation, the machine growth resulted in more money gained from shady deals, fraudulent contracts, as well as gambling, prostitution, and bootleg liquor; every establishment provided a cut of their profits to either the police or Pendergast's enforcers. However, as the 1930s progressed, it became impossible for Pendergast and his machine to hide their rampant corruption and fraud. Activists, political enemies, journalists, women's groups, and even an influential Rabbi spoke out about Pendergast's corruption. 

But Pendergast's biggest mistakes came within the world of politics. In 1932, he pledged delegates to an ally James A. Reed, a former mayor and Missouri Senator, instead of Franklin D. Roosevelt (FDR) at the Democratic Convention. Roosevelt retaliated by appointing Maurice Milligan, a Pendergast adversary, to the position of U.S. District Attorney for Western Missouri. Pendergast tried to appease Roosevelt by sending a 'New Dealer' to the Senate: Harry S Truman. When Harry departed for Washington D.C., Pendergast instructed him to "work hard, keep your mouth shut, and answer your mail."  

Pendergast also backed Lloyd C. Stark in the 1936 Missouri gubernatorial race, but after Stark won the governorship, he turned his back on Pendergast and began working to dismantle Pendergast's political network and influence. Stark appointed Pendergast adversaries to Kansas City election and liquor control boards. Stark successfully lobbied the legislature for a permanent voter registration law and control over the Kansas City Police Department. Most significantly, upon looking into Pendergast's deals with insurance companies during the mid-1930s, Stark summoned the Internal Revenue Service to audit Pendergast's income tax returns, leading to FDR ordering the Department of Treasury to conduct an exhaustive investigation of Pendergast; an indictment followed.

Pendergast represented a nationwide issue of machine politics, so it's no surprise that J. Edgar Hoover came to Kansas City to attend the trial of Boss Tom. The jury convicted Pendergast; he received a sentence of fifteen months in federal prison (Leavenworth Penitentiary). Additionally, the court banned Tom from all political activity, and he was not allowed to visit the now-historic headquarters during his probationary period. 

The court also forbade Pendergast from gambling because of the discovery of his severe gambling addiction, which he kept secret from family, friends, and political supporters. He lost as much as $6 million on horses alone. By the late 1930s, his debt to bookies and gamblers gave those he owed virtual control of Pendergast business, meaning he went to prison effectively broke, without control of his private enterprises, and politically ostracized.

In the wake of the trial, voters began electing "reformers" in droves, essentially driving out any of Boss Tom's people by the mid-1940s. Thomas J. Pendergast is buried at Calvary Cemetery on Kansas City's south side. His headquarters survives as a physical reminder of Boss Tom, the political machine he built, and the boss politics that dominated big cities throughout the nation.

Kansas City Public Library. "The Pendergast Years: Kansas City in the Jazz Age & Great Depression." Accessed August 29, 2022. https://pendergastkc.org/.

Millstein, Cydney and Mary Ann Warfield. "Registration Form: Pendergast, Thomas J., Headquarters." National Register of Historic Places. mostateparks.org. 2011. https://mostateparks.com/sites/mostateparks/files/Pendergast%2C%20Thomas%20J.%20HQ.pdf. 

Reid, Jr., Joseph D. and Michael M. Kurth. "The Rise and Fall of Urban Political Patronage Machines" in Strategic Factors in Nineteenth Century American Economic History, edited by Claudia Goldin and Hugh Rockoff. January 1992. http://www.nber.org/chapters/c6971.

Trounstine, Jessica. Political Monopolies in American Cities: The Rise and Fall of Bosses and Reformers. Chicago: University of Chicago Press, 2008.

Image Sources(Click to expand)

By unknown - Original publication: unknownImmediate source: http://www.applet-magic.com/pendergast.htm, Fair use, https://en.wikipedia.org/w/index.php?curid=40618983

Photo by David Trowbridge