The Decline and Fall of the Pendergast Machine

When it comes to assessing the trajectory of a political machine such as the one cobbled together over time by first Jim Pendergast, and then by his younger brother "Boss" Tom Pendergast, it is always best to follow the advice of the later Watergate journalists – that is, to “follow the money.”

Under Jim, the Pendergast machine seems to have dealt more in dispensing jobs and small favors, with Jim taking a rather small cut of the proceeds. Jim, however, could meet his relatively small personal needs, which included taking care of his bride Mary Doerr (married in 1886) and her young son by a previous marriage. He chose never to live “high on the hog.”

Home of Tom Pendergast
Home of Tom and Carolyn Pendergast at 5650 Ward Parkway. Courtesy of the State Historical Society of Missouri.

Tom, on the other hand, always seemed to need more money, especially after his own marriage to Carolyn Elizabeth Dunn in 1910. With two children born in two years in 1911 and 1912 (Marceline and Thomas Jr.), Tom and Carolyn began to think about building a home “out south.” This was completed in 1915 at 54th & Wyandotte, at which point Tom resigned his city council seat, never again to hold elective office. From that point, his control of city government would be established through his control of votes, wards, and local officials. In 1919, a third child, Aileen, was born. By 1926, the Pendergast “Goat” faction of the Kansas City Democrats had co-opted the Joe Shannon “Rabbits” along with Cas Welch’s East Side group that included the African American precincts. This provided much more stability for the Machine going forward. In 1928, Tom moved the family to their new mansion at 5650 Ward Parkway. It proved a much more expensive home to maintain.

In expanding the machine, or the Democratic Organization of Jackson County, as its proponents preferred to call it, Tom Pendergast developed a large array of business connections, beginning with the T.J. Pendergast Wholesale Liquor Co. (known as the City Beverage Company during Prohibition and after) and continuing with, in alphabetical order, the Atlas Beverage Company, City Beverage, Ready-Mixed Concrete, and W.A. Ross Construction. Tom Pendergast’s name appears as an officer of all these companies in the 1937 City Directory.

Tom and Carolyn Pendergast, 1935.
Tom and Carolyn Pendergast, 1935. Courtesy of the State Historical Society of Missouri.

Using additional sources, especially the books Tom’s Town, The Kansas City Investigation, and Missouri Waltz, it is possible to connect Pendergast with the following additional private businesses in Kansas City in 1937, two years before his downfall: Boyle-Pryor Construction, Centropolis Crusher Corporation, Dixie Machinery and Equipment, Glendale Beverage, Glendale Sales, Kansas City Concrete Pipe Company, Mid-West Paving, Mid-West Pre-Cote, Missouri Contracting Company, and Sanitary Service Company which held the trash collection contract for Kansas City, Missouri.

During the 1920s, Pendergast developed an insatiable desire for betting on the ponies. This led to a potentially profitable ownership, through surrogates, of a Platte County racetrack called the “Riverside Jockey Club” and a Clay County farm he outfitted as a stud horse breeding facility. While he may have had some income generated by the track and the farm, he most certainly did not generate income from his most avid pastime associated with it – horserace gambling. At one time in the late summer of 1935, a gambling publication quoted in The Kansas City Investigation, stated that from mid-August to mid-September 1935, Pendergast had wagered over $2,000,000 and had "gone overboard," or lost, $600,000. It would take many years of profits from all those companies to cover such a big betting loss.

Flyer for the opening of Riverside Jockey Club
Flyer for the opening of Riverside Jockey Club, 1928. Courtesy of the State Historical Society of Missouri.

Hence, Pendergast needed other sources of income that might be generated through his control of the city government of Kansas City, Missouri, by way of his right-hand man, Henry McElroy, the city manager from 1926 to 1939. The machine’s consolidation of power over city government occurred in 1925 when the city charter election permitted Pendergast to gain control of the city council. While unemployed people became ever more dependent on anyone who might be able to provide a wage-paying job, Pendergast and McElroy put together plans for a tremendous bond issue, known as the Ten-Year Plan, that would do just that. In the meantime, with ingenuity, the revenues became a source of major floating funds that passed through the City Manager's "Emergency Fund" to be used with little discretion or oversight. It paid thousands of machine-controlled workers who simply received paychecks for supplying no work for the city, and then passed on most of the proceeds to the Pendergast's bookkeeper, Ernest L. Schneider.

Henry McElroy
Henry McElroy. Courtesy of the State Historical Society of Missouri.

Even before the election of Franklin Roosevelt to the presidency and his New Deal policies, Kansas City voters approved the Ten-Year Plan in May 1931. The ability to shift funds about became much easier with time, as federal programs such as the PWA and WPA took over much of the actual construction of facilities promised in the bond measure. It turns out that this allowed for “reassignment” of bond monies to other city uses such as paying employees to work who never did anything but pick up their paychecks, turn the funds over to the Pendergast bookkeeper, and receive a percentage in return for their trouble.

Pendergast’s power increased to possibly its peak level in 1932, with the establishment of Home Rule police control and the selection of Missouri governor & U.S. representatives. Control of Governor Guy Park meant that Pendergast could gain an appointment for his friend and former business associate, R. Emmett O’Malley, as commissioner of insurance for the state of Missouri. For Kansas City, Home Rule meant that for the first time since the 1870s, Kansas City controlled its own police department. Prior to the Supreme Court decision, and again after the Pendergast era closed in 1939, the police were under the direction of a governor-appointed Board of Police Commissioners.

Home Rule for the Kansas City police department came with a Missouri Supreme Court decision in March 1932. City Manager McElroy had challenged the governor-appointed, Republican-controlled Kansas City Police Board of Commissioners many times over their right to set whatever budget they wished with the city required by Missouri state law to pay the amount. Surprisingly to McElroy and to the police board, in March 1932 the Missouri Supreme Court agreed with McElroy's interpretation and ruled that portion of Missouri law to be unconstitutional. This gave control of the police department to the city, which was ultimately responsible for paying the cost of policing in the city out of tax revenues. McElroy immediately got the city council to pass an ordinance organizing the police as a department of city government with a director who reported directly to McElroy himself.

Police controlled by city hall ultimately gave free rein to Pendergast and the machine, along with a sense of invulnerability. This overconfidence very likely allowed Pendergast to lessen his considerable judgment on more questionable political and governing activities in the future.

One of the first individuals to recognize this possibility was a local Jewish rabbi, Samuel S. Mayerberg. Kansas City got a first peek at the opposition position to the Pendergast Machine when Rabbi Mayerberg gave what was expected to be an innocuous talk to the women’s luncheon Government Study Club in May 1932. He called the electoral and local governing tactics of the machine into question, largely on moral grounds. This was a line of argument that many would pursue alongside Rabbi Mayerberg with little success over the next seven years.

Another addition to Tom Pendergast's influence, this time at the state and national level, arrived because of a reapportionment conflict in the state. Because of reapportionment after the 1930 census, Missouri went from 16 to 13 seats in the U.S. House of Representatives. As a result of a deadlock over how to redistrict between the Republican governor and the Democratic majority in the legislature, all House of Representatives candidates had to stand for election at-large across the state. Because Pendergast could reliably produce the largest predictable bloc of votes in the state, he was able to endorse whomever he pleased for the Democratic nominees in all 13 seat races. Every one of the Democrats won, although this was also the landslide election for Franklin Roosevelt, so Pendergast's huge margins in Kansas City and Jackson County were only part of the election totals.

Guy Park
Missouri Governor Guy Park. Courtesy of the Missouri Valley Special Collections.

Shortly thereafter, new opportunities developed in the Missouri governor’s race. The primary was held in August and the general election in November. Pendergast endorsed the leading candidate for Governor, Frances M. Wilson. When Wilson died between the primary and general elections, Pendergast personally picked Judge Guy Park, a long-time friend of Wilson and his wife, who may have suggested Park's name to the Boss, to run in Wilson's stead. Every Democratic candidate won in the house races, as did Park in the governor’s race.

By year’s end in 1932, Pendergast probably stood at the peak of his power between the death of his brother Jim in 1911 and his own political demise just seven years later. Certain Pendergast-endorsed representatives stood poised to enter national government while Pendergast’s influence spread in the state government in Jefferson City. The current or incoming Missouri members of the U.S. House of Representatives all owed the Pendergast organization a debt for the large votes contributed in the general election. Governor Guy B. Park assumed office early in 1933, assuring Pendergast wide influence for the first time in state governing. The thoroughly reorganized Kansas City Police Department stood ready to do the bidding of McElroy, and thus of Pendergast as well, in what would become the “wide open” year of 1933.

Letter from Tom Pendergast to Gov. Guy Park
Pendergast was able to secure state appointments for many of his cronies, due to the allegiance of Governor Guy Park. Courtesy of the State Historical Society of Missouri.

Several minor stumbling blocks developed along the way, but nothing effectively derailed the smooth-running Machine in 1933-34.

One such "bump" was the "Union Station Massacre" that occurred June 17, 1933. An attempt to free a federal prisoner being taken to Leavenworth Penitentiary resulted in the death of the prisoner as well as three police officers and an FBI agent. Pendergast ally Johnny Lazia was later implicated in the planning for the escape attempt. One shooter has been positively identified as a mobster named Verne Miller, who was only charged with obstruction of justice. The other shooter, or shooters, (eyewitnesses could not agree on whether it was two or three men) have never been fully identified, although the FBI settled on Charles “Pretty Boy” Floyd and Adam Richetti as the fall guys. Within a year all three were dead, with only Richetti dying by official means when he was executed in Jefferson City for the crime he almost certainly did not commit (although he had committed dozens of other crimes previously).

Aftermath of the Union Station Massacre
Aftermath of the Union Station Massacre. Courtesy of the Missouri Valley Special Collections.


Gambling always remained a touchy subject in Kansas City during the Pendergast era. On the one hand, gambling was the lifeblood of the speakeasies during Prohibition and of the saloons across the city both before and after that social experiment. Liquor dispensing establishments were very important to Tom’s continuing interest in the available supply of fermented or distilled beverages even during Prohibition. In the 1930s, however, gambling expanded into department stores, drug stores, and mom-and-pop grocery stores with the adoption of slot machines, or “one-armed bandits” as their detractors preferred to call them.

The Pendergast machine wound up with mixed opinions on whether the slots were a good thing for the citizens of the city. Pendergast-endorsed County Prosecutor Jim Page fought hard against slot machines up to the end of his six years in the post in 1932. Pendergast’s vital ally Henry McElroy, on the other hand, took a more measured approach. First, he said that the man who played a slot machine was "a sucker, pure and simple." Then he opined that, “if there is an agitation in this city against slot machines, I will order their removal from the larger stores that can afford to pay for morality. But I will not remove them from small, independent stores,” because McElroy believed profit from the slots kept the little stores in business.

What McElroy did not have to say on behalf of Pendergast was that any store, large or small, that offered slot machine "entertainment" had to pay for protection from police interference. Those payments were collected by machine enforcers such as Johnny Lazia and Charley Carrollo. At that time, the legality of slot machines was at least vaguely under the local authority, but such legality could be withdrawn in a specific instance at any time if the weekly payment had not been made. This was even more the case for the questionable card and crap games that went on in almost every liquor-dispensing facility, legal or illegal, in the city.

Of course, there was also the third element of the crime trifecta at the time – prostitution. Speakeasies, jazz clubs, and public gathering places tended to attract prostitutes along with politicians and businessmen. They, or their representatives, had to pay regular amounts to the enforcers to stay out in the open where they could solicit business.

The result of this arrangement was that the machine could rake off the top layer of revenue from all these illegal or questionable activities. If those who plied these trades did not make the expected payments, the McElroy-controlled police could step in to shut down the illegal side of any of these enterprises. The fact that the police were essentially part of the machine after 1932 increased the effectiveness of the entire protection scheme. It also increased the machine’s self-confidence, which, in turn, tended to generate excess or carelessness.

An example of the latter came with the Union Station Massacre in 1933. Another arrived in early 1934, as the chief enforcer came in for a little heat from the Internal Revenue Service and the Federal District Attorney. Johnny Lazia had always operated right on the edge of illegality. His enforcement duties demanded it. As a means of protecting himself, he inserted himself into the selection process for the police department, apparently with Pendergast’s approval. However, that did not insulate him from “harassment” from higher up. Because he lived rather well, with a nice penthouse apartment in the new Park Central apartments near the intersection of Armour Boulevard with Gillham Road, the fact that his declared earnings on his income tax returns seemed meager for his lifestyle caught the attention of federal authorities.

In a foreshadowing of what would happen to Pendergast himself just a few years later, Tom’s efforts to call off the investigation of Johnny Lazia proved fruitless. The best the Boss could do was to get Lazia free on bail during the appeal before he would likely have to start serving time for income tax evasion. On the night of July 9, 1934, as Lazia was returning from his collection efforts with his wife Marie beside him and his driver Charley Carrollo, he was gunned down at the entrance to Park Central. Carrollo successfully got Lazia’s wife whisked away, but Lazia died a few hours later. The crime was never solved officially, but later investigations indicated the likely assassins were rogue gang members who, shortly thereafter, died violently themselves.

Park Central Apartments
Park Central Apartments, where John Lazia was gunned down in the street. Courtesy of the Missouri Valley Special Collections.

Both events signaled to anyone who paid attention that Tom Pendergast, who prided himself on being in control, was not nearly as effective as he thought. It was another indication of the beginnings of troubles for the machine in its illegal, but quite profitable, protection business.

Possibly the most costly election in machine history occurred in April 1934 before the exit of Mr. Lazia. The Kansas City elections for city council and mayor, on the one hand, resulted in almost complete continuing control for the machine. In the process, however, an organization of mostly young business types with money and influence was able to get two members elected to the council. In and of itself, these "New Youth Movement" councilmen could accomplish very little, but their presence could be annoying as they pointed out what they considered to be errors in judgment by City Manager McElroy and the machine-dominated majority.

Additionally, the 1934 city election day was marred by four killings, shootings, intimidation, and extensive voter fraud to such an extent that it elicited the interest of Federal Judge Albert Reeves, who convened grand juries to investigate. Over the next four years, these grand juries indicted hundreds of machine operatives on a variety of charges ranging from ghost voting to outright intimidation of opposing voters. However, not one of the convicted persons would "roll over" on the higher-ups in the machine. For all their cleansing of the voter rolls of the dead, which greatly reduced ghost voting by the time of the 1938 city election, the convictions barely put a dent in the public support for the machine. The 1938 city elections, after all the purging of voter rolls and convictions of fraudulent voters, still produced solid machine majorities for eight out of nine machine candidates for city council and the mayoralty. This was up one seat from the 1934 totals.

Clearly, the slow, time-consuming work of chipping away at the machine one precinct captain or ghost voter at a time was not going make a great difference. Pendergast would have to make an even bigger mistake, and get caught at it, in order to be thoroughly discredited.

By far, the single most important payment of money in Tom Pendergast's long and storied career occurred in installments paid to Pendergast between May 1935 and April 1936. Over that year, Pendergast received $440,000 from a consortium of insurance companies for services rendered in obtaining a settlement of an outstanding case involving a total of $9,020,279 in impounded funds. Tom Pendergast was not a greedy man; he kept only part of the money. He remitted $62,500 to his friend R. Emmet O'Malley, a former insurance company partner and then the Missouri insurance commissioner. Another $62,500 went to A.L. McCormack, a St. Louis insurance company representative who facilitated the transaction.

Some background is in order. In 1922, the Republican commissioner of insurance for Missouri had ordered fire insurance companies to reduce premiums charged to customers in Missouri by 10 percent. In 1928, the U.S. Supreme Court upheld the authority of the insurance commissioner in Missouri to require such a reduction. The insurance companies responded in late 1929, after the Wall Street crash, by announcing that they were raising rates in Missouri by 16.67 percent. Again, the commissioner refused to allow the increase. The companies sued. At the filing, the Missouri court ruled that until the case was decided, the "excess" premiums (above the amount approved by the Commissioner) would be collected from the customers but then impounded in the hands of a custodian until the cases could be decided.

This litigation had dragged through the courts from 1929 to 1935 with the amount of impounded "excess" premiums rising to the aforementioned $9 million figure by the latter year. In the midst of the Great Depression, the companies were willing to do almost anything to get their hands on at least part of this large sum.

The key figure for the companies was Charles R. Street, a company officer and the chair of the Subscriber’s Actuarial Committee, an insurance company association entity that basically regulated the activities of insurance companies in the western part of the United States from Street’s office in Chicago. This was a secretive committee because it was technically operating in restraint of trade purely on behalf of the insurance companies. This latter aspect of its duties included setting rates and lobbying in common on behalf of all members. The very existence of the committee was of questionable legal status because of its rate-fixing activities.

According to the federal investigators who looked into the affair, Street ran this committee as an extension of his own dictatorial personality. By 1935, Charles Street decided enough was enough with the impounded funds in Missouri. By that time the Missouri insurance commissioner, as previously noted, was Emmet O’Malley.

On May 14, 1935, Street, Pendergast’s crony O’Malley, and several other parties including Street’s friend A.L. McCormack of St. Louis, met in Kansas City and hammered out a compromise whereby the companies got 50 percent of the impounded funds directly, 30 percent went into a trust fund out of which Street and an insurance company attorney would pay expenses of various sorts with any remaining balance afterwards distributed to the insurance companies, and 20 percent would be returned to the customers who had paid the premiums in the first place. The second "Missouri Compromise," as newspapers dubbed it almost immediately, was heavily weighted in favor of the companies. Presumably, the $440,000 paid to Pendergast came out of the trust fund.

The reason Tom Pendergast participated in this transaction, which was perfectly legal from his standpoint, was to use his influence to get a favorable decision on behalf of the insurance companies. What Pendergast failed to do was declare that money as income on his tax return. Because he had paid off O’Malley and McCormack, who were the only ones directly involved besides Street himself, Tom Pendergast almost certainly believed he had gotten away with it. While it will never be known for sure, the most likely destination for the $315,000 retained by Pendergast went to pay off his bookies for his bad bets on the ponies.

Excerpt from Emmet O'Malley trial
Excerpt from the indictment, U.S. vs. T.J. Pendergast, R.E. O'Malley, and A.L. McCormack, detailing part of the fire insurance payoff. Courtesy of the National Archives at Kansas City.

Literally weeks after Pendergast received the last scheduled payment from Street and McCormack, and while he was attending the 1936 Democratic National Convention in Philadelphia, Tom suffered a most serious heart attack. He and Carolyn were staying at the Waldorf Astoria in New York, so the convention visit was a daytrip. Following the heart attack, it was discovered that he had a bowel blockage requiring further surgery. From the summer of 1936 until his death in 1945, Tom Pendergast had to wear a bag to empty his bowels following his colostomy. He was never again a well man.

In the same year that Tom Pendergast received the last of the “Missouri Compromise” payments and in which his physical condition declined substantially, a routine IRS inspection of the accounts of a now-dead partner of the legal firm that advised Street and the Insurance Subscriber’s Committee, turned up receipts of checks totaling $100,500 received from several insurance companies. The Kansas City Investigation indicates that this substantial sum was then disbursed to Charles Street. This accidental discovery set in motion the investigation that ultimately led to the indictment of Tom Pendergast and R. Emmet O’Malley for income tax evasion.

R. Emmet O'Malley mugshot
R. Emmet O'Malley upon entering Leavenworth. Courtesy of the National Archives at Kansas City.

The investigation began in Chicago in April 1936, and took many twists and turns before Tom Pendergast stood in arraignment in Kansas City on Good Friday, 1939. Much of what fueled the investigation was a series of serendipitous events and a great deal of hard investigatory effort by a total of 26 agents of the Treasury Department and the IRS. While considerable attention has been paid in most accounts to the efforts of Federal District Attorney Maurice Milligan and Governor Lloyd Crow Stark (who himself had received Pendergast’s endorsement in the 1936 gubernatorial election), as well as to the perceived support of Franklin Roosevelt for pursuing the lower level machine participants in the ghost voting and other voter fraud cases, the fact remains that what ultimately brought down Tom Pendergast and his carefully crafted machine was the fact that he thought he could get away with obtaining $315,000 legally, but not declaring it on his income taxes.

Ultimately, many things brought down the Pendergast political machine. Certainly, hubris should be high on the list. For so many years, Tom Pendergast and those around him thought they were invulnerable. They believed that their funding of the repetitive combination of “vote early and often” would last forever. It turned out that it was all a house of cards that came tumbling down once the corruption became clear. While the efforts by Pendergast operatives to intimidate and cajole would last for some time after Tom Pendergast entered the Leavenworth Federal Penitentiary in May 1939, they never carried the weight they had before, and a “clean sweep” reform government swept into office in 1940. Pendergast served one year of his 15-month term, being released on a five-year parole for good behavior and with a requirement not to engage in politics. He also paid a plea-bargain reduced amount of $430,000 in back taxes, penalties, and interest, as well as a $10,000 court fine. Tom Pendergast never recovered his health and died from a heart attack on January 26, 1945.

Mugshot of Tom Pendergast, May 1939.
Mugshot of Tom Pendergast, May 1939. Courtesy of the National Archives at College Park.

While the direct cause of Pendergast’s personal downfall was his refusal to stop gambling, the machine faltered in large part because of attacks by reformers inside and mostly outside of city government. It is quite possible that no one, including Pendergast, realized how much the Machine’s continued influence depended on the myth of its invincibility. Once Pendergast pled guilty to charges of income tax evasion, the whole apparatus appeared vulnerable.

The political reformers had concentrated their electoral efforts on opposing members of the City Council from 1934 forward. Their main problem in 1939, after Pendergast was sent to Leavenworth, was that upwards of three years remained in the Pendergast majority’s terms on the council. Opponents were aided by the resignation and death of Henry McElroy as city manager, but even a change in that office did not fully turn things around.

Ultimately, the opposition to Pendergast gained a charter change that called for new elections two years early in 1940. This was aided by a partial turnaround in position by previously Pendergast-controlled Mayor Bryce Smith. In the winter of 1940, campaign efforts coalesced in the form of a “Clean-Sweep” effort headed by the now resurgent Citizens Association, made up of reformers, Republicans, and other dissidents to the long-dominate Goat faction of the Democrats.

Women came to play a very important role in the campaign because Kansas City’s business elite, which funded the Clean-Sweep effort, was hesitant to put men in public positions of opposition. Mrs. Claude Gorton of the Woman’s City Club marshaled the forces of women’s groups in the city, such as the Athenaeum and women’s church organizations. They persuaded attorney John B. Gage to run for Mayor and endure the hidden and open attacks waged by the remnants of Pendergast’s forces, which were led by Tom’s nephew James Pendergast.

John B. Gage
John B. Gage won the mayoral election of 1940. Courtesy of the Kansas City Museum.

The effort was not entirely successful in that at least one Pendergast loyalist survived the election referendum, but Gage won along with seven of the Citizens’ candidates. They, in turn, appointed L.P. Cookingham to be the first professionally trained city manager in the city’s history. Cookingham immediately went about purging the city’s employment rolls of employees whose purpose had been simply to serve the needs of the machine. He also brought about a real accounting of the city’s income and expense. Aided by a complete reevaluation of property taxes and the prosperity brought to the city by World War II industries, Cookingham returned Kansas City’s budget to positive territory by 1945. The era of Pendergast was gone for good.

During his lifetime, several people sought the glory of having "brought down Pendergast." Both Governor Stark and Federal District Attorney Maurice Milligan claimed that title in their run against Harry S. Truman for his senate seat in the 1940 Democratic primary in Missouri. They tended to cancel each other out, though, and Truman won by just over 8,000 votes statewide. Additionally, some blamed or credited President Roosevelt for not interfering with Milligan’s investigations.

Ultimately, a combination of Tom Pendergast's own failings, most particularly his need to bet on horseraces and his personal pride, along with an overblown sense of invulnerability, as well as dogged investigation by federal agents seeking tax evasions of other, seemingly unrelated individuals, brought it all to an end.


Funding for this essay is generously provided by the Missouri Humanities Council with support from the National Endowment for the Humanities.