When 199 Men Attempted to Run Across the US on Route 66

The 1928 Transcontinental Foot Race, better known as the “Bunion Derby,” was one of the most ambitious sporting spectacles of the Roaring ’20s. The grueling 3,422-mile race promised to promote the newly established Route 66, but it left its mastermind, sports promoter Charles “C.C.” Pyle, nearly bankrupt.

Nicknamed “Cash and Carry,” Pyle was America’s first sports agent and one of the era’s savviest promoters. By age 45, he owned five theaters, had negotiated a $100,000 contract between star running back Red Grange and the Chicago Bears and represented amateur tennis players as they turned professional.

But within a year, Pyle was $100,000 in debt and facing numerous lawsuits over unpaid wages and bills. His grandest promotion—the Bunion Derby—had become his costliest failure.

Route 66 was just a year old in 1927 when Pyle and a group of Route 66 Highway Association members conceived the idea for a cross-country race to promote the Chicago-to-Los Angeles highway. Participants would race east on Route 66, reach Chicago, then continue all the way to New York City.

The Tour de France–style stage race offered a $25,000 prize to the runner with the fastest cumulative time after 84 days, plus another $23,500 divided among the second- through 10th-place finishers. In exchange for financial backing, Pyle agreed to bring his traveling circus to cities along the route. The carnival sold hot dogs and featured Egyptian belly dancers and a five-legged pig.

“In the evenings, everybody would be at the finish line cheering for [the racers], and then they could buy things,” says Geoff Williams, author of C.C. Pyle’s Amazing Foot Race. “[Pyle] knew people would spend money there, and it would be good for the towns.”

Pyle promised the runners free food, lodging and medical attention in exchange for their suffering (and a $125 entrance fee). A support staff included doctors, nurses, dietitians, a podiatrist, massage therapists and an “expert shoe repairman,” author Charles Kastner described in Bunion Derby: The 1928 Footrace Across America.

The race cost more than $350,000, with Pyle personally fronting $100,000, according to Bunion Derby. He expected to recoup the investment through financial pledges from towns along the route as well as carnival receipts and advertising revenue.

Ahead of the race’s first stage, Pyle held a three-week training camp at Ascot Speedway in the Los Angeles neighborhood of El Sereno. International runners arrived with trainers, Williams wrote, and blue-collar competitors showed up with supportive family members. In total, 275 men came to train.

Pyle used the time to drum up publicity for the race and made some quick cash, too. He charged runners for meals and spectators admission to watch the competitors jog the dirt track.

After many would-be entrants dropped out during training camp, 199 runners arrived at the start line on March 4, 1928. They included world-record holders, Olympians, race walkers, cooks, fishermen and wrestlers. While the Bunion Derby wasn’t open to women, it did include Native American and Black runners.

Eddie Gardner was one of several Black runners who risked their lives competing alongside white people through the segregated South. After winning multiple stages in the first half of the race, Gardner was instructed to keep a low profile through Texas after his victories over white runners had enraged the Ku Klux Klan, Williams wrote, referencing a Baltimore Afro-American newspaper article from the time. Gardner went on to finish eighth in New York, taking home $1,000.

Also at the start line was Andy Payne, a 20-year-old Cherokee farmer from Claremore, Oklahoma, who came to running through his dislike of riding horses. Payne’s father told The Daily Oklahoman he gave Andy his blessing to participate after realizing he “couldn’t get no work out of him, he sprinted from morning till night. I let him go and I think he’ll win.”

A federal highway designation did little to immediately improve Route 66, which at the time mostly consisted of rock, gravel and dirt rather than asphalt. From the muddy dirt track, the runners traced California’s San Gabriel Valley eastward to the San Bernardino Mountains, where they went up and over the Cajon Pass and through the Mojave Desert.

“The landscape and the terrain were so rough that a lot of people dropped out right away,” Williams says. “They couldn’t hack running in the desert and the mountains.” The race lost roughly 80 contestants before it hit Nevada.

The remaining runners endured ferocious winds in Arizona’s high country and slogged through stretches of deep mud in the Texas panhandle before conditions improved across the Midwest. All the while, thousands upon thousands of spectators lined the roads to cheer on the contestants, though fewer people attended the carnival than Pyle would have liked.

As the derby wore on, the mileage wore on the competitors in the form of blisters, sprained ankles, lost toenails and even infected teeth. While much was promised in terms of accommodations, some runners eventually soured on what Pyle delivered. Nutrition was lacking, and there was no laundry service. Former Alaskan dog sledder Harry Sheare nearly died when a car hit him as he approached Cleveland.

“Nobody was killed, thank God, but there were a lot of injuries,” Williams says. “It was brutal on the body.”

The Bunion Derby ended at Madison Square Garden in New York City on May 26, 1928, with 55 of the original 199 entrants still in the race. Payne won with a time of 573 hours, 4 minutes and 34 seconds, averaging 10 minutes per mile and taking home more than enough money to buy his family’s farm from the bank as well as invest in other land.

That the prize checks materialized on time came as something of a surprise to some contestants, Kastner wrote, given their knowledge of Pyle’s money troubles. Numerous towns along the route had stiffed Pyle on promised fees, prompting the organizer to reroute the course around them in retaliation. The carnival also generated less income than Pyle expected, and the once-rich promoter had to lean on friends to come up with the prize money.

Even so, Pyle held the race again in 1929 and made a few key alterations: He offered more prize money for the lower placings, meals and housing were no longer provided, and the route left Route 66 and the towns that burnt Pyle in the first edition. He also reversed the course to avoid losing so many runners right away in the mountains and deserts of California, Williams says.

Despite a close finish in front of a packed ballpark crowd, Pyle ultimately stiffed the 1929 field. Winner Johnny Salo, who at least won $10,000 for his second-place finish in 1928, went into the Great Depression no richer for his 78-day 1929 effort. Pyle eventually regained some of his fortune by managing Robert Ripley’s “Ripley’s Believe It or Not” exhibit at the Chicago World’s Fair before his death in 1939.

Contrary to the physicians of the era, who believed the Bunion Derby took up to a decade off contestants’ lives, Andy Payne spent his remaining 49 years as a newspaper editor and clerk for the Supreme Court of Oklahoma. Asked why he entered in the first place, Payne said, “I just thought I could do it.”