Stranger Than Fiction

September 2025

The Will Rogers Lottery Swindle
by Dean Jobb

The single-engine floatplane was headed for Point Barrow, the northernmost point of U.S. territory, when the pilot landed on a remote lagoon to ask for directions. Wiley Post, the first man to complete a solo around-the-world flight, was touring Alaska. His passenger, who was filing newspaper columns documenting their adventures, was Post’s friend, a fellow Oklahoman, and one of the most famous people in America—the writer, comedian, and Hollywood star Will Rogers.

When an Indigenous hunter told them they were fifteen miles southwest of their destination, they roared back into the air. Within moments, the engine stalled and the plane plunged into the lagoon, killing both men instantly.

Rogers’s sudden death at fifty-five shocked the world. He was a cultural icon, a folksy, dry-humored everyman who poked fun at politicians and offered a common-sense take on world events. Amid the glitz, excess, and corruption of the live-for-today Jazz Age, he was the nation’s down-to-earth conscience.

He began his career as a rodeo rider and graduated to vaudeville and Broadway, doing rope tricks in his cowboy garb as he cracked jokes. To keep his routine fresh, he scoured the daily papers for new material. “All I know is just what I read in the newspapers” and “I never met a man I didn’t like” became his trademark phrases. He made the cover of Time and another magazine dubbed him “the philosopher with the lariat.” Millions read his daily musings in the newspapers, listened to his radio program, watched his movies. “This wise, sane, wholesome man of Oklahoma’s plains,” noted one of the state’s small-town newspapers, restored the public’s faith in “simple honesty and simple living.”

The reaction to his death, notes biographer Ben Yagoda, “was such as you would expect the passing of a beloved President to engender.” Flags flew at half mast across America and 12,000 movie theater screens were darkened for two minutes as a tribute. Rogers was eulogized on the floor of the Senate as the nation’s “most widely known private citizen and certainly the best beloved.”

Governments and institutions were eager to honor the star. A statute commissioned before his death stands in the U.S. Capitol—Rogers joked he would be able to “keep an eye on Congress”—and presidents have been known to touch its shoe for luck on their way to deliver the State of the Union address. His name popped up on more than a dozen public schools in his home state. A mountaintop tower and chapel in Colorado Springs, under construction when Rogers died was christened the Will Rogers Shrine of the Sun. In Fort Worth, Texas a Will Rogers entertainment complex hosts equestrian events and livestock shows.

Donations poured in to the New York based Will Rogers Memorial Commission, formed by a group of the entertainer’s friends to fund university scholarships and a hospital in Saranac Lake, New York, that bears his name. Within a decade it collected more than two-million dollars, equivalent to thirty-seven million today. His widow, Betty Rogers, donated land in Claremore, Oklahoma, near his birthplace, to build the Will Rogers Memorial Museum, which opened in 1938.

In Chicago, a former newsboy and newsstand proprietor took note of how Rogers’s name attracted attention and money. Abraham Zimmerman wanted a piece of the action.

Zimmerman was only thirty-four when Rogers died, but he was already known as the “king of the lotteries” and oversaw a network of sales agents that operated in every state east of the Rocky Mountains. His minions sold tickets on anything a gambler might find enticing to bet on—horse races, baseball games, even a “Gold Bond” lottery that awarded prizes to players whose tickets matched digits in the U.S. Treasury’s weekly balance sheet. Tickets sold for between fifty cents and two dollars each—cheap enough to attract low-income buyers desperate for a big win—and the proceeds added up. Federal investigators estimated Zimmerman was raking in a million dollars a year and paying a pittance in prizes to keep the suckers buying. In 1929 alone his net income was estimated to be more than $162,000, which works out to almost three-million dollars today.

Chicago boasted its own Will Rogers Memorial Hospital, located on North Clark Street in Rogers Park (the neighborhood’s name was a coincidence—the area’s original landowner was an Irish immigrant, Phillip Rogers). It received no funding from the Will Rogers Commission and its operators had not asked the Rogers’s family for permission to use the name. To Zimmerman, it was a perfect front for a new lottery.

In the summer of 1937 he met with the hospital’s top administrator, Dr. Frank Deacon, a respected surgeon who had set up base hospitals for the American Red Cross during the Great War. Deacon would later insist that Zimmerman offered to organize charitable events—from theatrical performances to boxing matches, skating parties, and rodeos—to raise money for the hospital. Zimmerman, however, claimed he was upfront and Deacon knew he was selling lottery tickets. To seal the deal, he wrote a check for five-thousand dollars—more than $100,000 today—to aid the hospital.

Zimmerman’s print shops churned out millions of half-dollar tickets to support the hospital. Four hundred winning tickets would be drawn each month, buyers were assured, and a total of twenty-thousand dollars in prizes would be distributed. To boost sales, Zimmerman produced and distributed a glossy brochure that included photographs taken at the hospital. The Rogers lottery, he promised his far-flung network of distributors, had the makings of “another Irish sweepstakes.”

It was illegal to run a lottery anywhere in the country. It was even an offense to import or sell tickets for the famous sweepstakes that supported Irish hospitals, but that did not stop thousands of Americans from trying their luck. The era of state-run lotteries was decades away. In the meantime, Zimmerman was the Al Capone of illegal ones.

Zimmerman’s agents cast a wide net to find ticket sellers and 120 Will Rogers tickets were mailed to Ross Lewis, a resident of Peoria, Illinois. A cover letter asked him to send the proceeds to an address in Chicago and to keep twenty tickets as compensation for his sales efforts. Unfortunately for Zimmerman and Deacon, Lewis was a police officer. He alerted officials of the Better Business Bureau, who lobbied Illinois Attorney General Otto Kerner to take action.

The state took the hospital to court, alleging it was operating a lottery in violation of its charter. Deacon claimed it was a valid fundraising campaign and not a game of chance. The holders of tickets drawn, he explained, would be asked to submit an essay on the subject “Why a Hospital Is The Best Charity to Support,” and only the authors of the best essays would win prizes. Tickets and promotional materials, however, made no mention of this requirement.

Judge Harry Fisher of the Cook County Circuit Court dismissed Deacon’s flimsy defense and revoked the hospital’s charter in February 1938. Days earlier, lawyers for the Will Rogers Memorial Commission had secured an injunction that barred the hospital from using Rogers’s name. Deacon and other administrators were dismissed and the facility was renamed Physicians Hospital.

The judge also ordered the hospital to turn over its lottery records to the authorities for examination. U.S. Post Office agents launched an investigation into what the Chicago Tribune termed “a nation-wide lottery in the guise of a charity fund.” A trail of tickets, print shops, and. small-fry sales agents led them to Abraham Zimmerman.

The raids and arrests began within weeks of the court’s order to rename the Chicago hospital. Two of Zimmerman’s sales agents were picked up in St. Louis and tickets were seized. One of the men claimed he had refused to sell the Will Rogers tickets. “The lottery was a fake,” he admitted, “and I wouldn’t deal in anything that isn’t legitimate.” A search of a New Jersey warehouse turned up Rogers tickets hidden in boxes labeled “candy.” Postal agents in Chicago and other cities scooped up printing presses and more than fifteen tons of tickets, brochures, and other records. In fifteen years, investigators reckoned, Zimmerman’s lotteries had raked in a staggering twenty-million dollars, a figure in the half-billion-dollar range today.

The Post Office’s investigation was assigned to its New England division, which was based in Boston and had a solid track record of probing and prosecuting mail fraud and illegal lotteries. A grand jury heard testimony from more than 100 witnesses from across the country, including police officers, postal inspectors, undercover operatives, ticket sellers, and print-shop employees. Betty Rogers was summoned to confirm that neither the Rogers family nor the memorial committee had sanctioned the lottery.

In September 1939 Zimmerman, Deacon, and seventy other people in twenty states were indicted on charges that included conspiracy to promote an illegal lottery, using the mail to commit fraud, and shipping tickets for an illegal lottery across state lines. Those accused included a couple of former Chicago cops, the head nurse at Deacon’s hospital, and a former University of Chicago football star. It took six months to round up all of the suspects. Seventy-one, including Zimmerman, pleaded guilty; most were fined, put on probation, or served short jail terms.

The lone holdout was Deacon, who stood trial in Boston in May 1940, against the backdrop of Hitler’s invasion of France. The prosecution’s star witness was Zimmerman, who by now was serving a twenty-month prison term for tax evasion—he had failed to report the bulk of his lottery income. He confirmed his deal with Deacon to use the Will Rogers Hospital’s name to promote a lottery. The doctor, he said, was shown proofs of the tickets before they were printed.

Deacon, however, testified he had not realized he was dealing with the notorious Lottery King Zimmerman had used the alias Joseph White in their discussions—or that he was helping to set up an illegal lottery.

A jury deliberated for eleven hours before convicting Deacon of two counts of shipping illegal lottery materials across state lines. He was sentenced to a year in a federal penitentiary. Zimmerman was sentenced to a year in prison and ordered to pay a fine of twenty two-thousand dollars.

The Boston Globe wondered how America’s beloved cowboy comedian would have reacted to the hoodwinking of so many of the ordinary people he championed. “Wish we could have a paragraph from Will Rogers on the running of a fake lottery by the use of his name,” the paper noted. “It would be pungent.”

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Dean Jobb’s latest true crime book, A Gentleman and a Thief: The Daring Jewel Heists of a Jazz Age Rogue (Algonquin Books and HarperCollins Canada), is a New York Times Editors’ Choice and a national bestseller in Canada. It’s the story of Arthur Barry, who charmed the elite of 1920s New York City while planning and executing some of the most brazen jewel thefts in history. Find him at deanjobb.com.