We’re talking horse racing on this Archiver, something not associated much with Kansas. But, for an amazing two minutes and four seconds in 1938, a horse from Johnson County was the top three-year-old in the land. It was owned by a man who was better known for suits than stallions, and who had an odd connection to Kansas City political boss Tom Pendergast.


The horse was named Lawrin. He was trained at the 200 acre Woolford farm which is now part of Prairie Village, right around 83rd and Mission Road. Lawrin came from a pretty good line. His grandsire was Sir Gallahad, a French Thoroughbred horse and one of the most important sires in American racing. Woolford Farm was named after Herbert Woolf, the president of Woolf Brothers, one of the most important clothing stores in Kansas City history. 

Lawrin was the only Kansas bred horse to ever win the Kentucky Derby, and he gave a big boost to the careers of the man who trained him, Ben Jones, and the jockey who rode him, Eddie Arcaro.

Lawrin's victory is a standout moment for a state not particularly known for its history with horses, but Archiver historian Virgil Dean says there’s more horse history in Kansas than one might think.

“Certainly when settlers started moving into the Kansas Territory in the 1850s, horses were important to people at the time,’ Virgil says. “They were the primary source of power for transportation and agricultural purposes.”

But people were also interested in leisure time activities, and in the late 19th century that often meant horse competitions.

“As early as 1858, before Kansas is even a state, you have the first county fair in Leavenworth County and there’s an emphasis, among other things, on horses,” Dean says. “Douglas County has its first fair the next year, and they specifically talk about races and a women’s equestrian event that attracts a lot of attention. So, there is an effort to focus attention on the importance of good horses and breeding from very early on.”

The 1938 Kentucky Derby was run on May 7. It was partly cloudy and the track was fast. Lawrin was an 8-1 long shot even though the colt had a pretty good year. He had already won the Hialeah Stakes, the Hollywood Trial Stakes, the American Invitational and the Flamingo Stakes before the Derby. 

Lawrin would come from behind and win by four lengths.


Here’s how the Louisville Courier-Journal described the scene as Lawrin entered the winners circle with 22-year-old Eddie Arcaro aboard and owner Herbert Woolf thrilled with the come-from-behind win. 

“Straw-Hatted, wearing a dark blue suit and a maroon and gray striped silk tie, Mr. Woolf made no secret whatever of the fact that he was just about as elated as it was possible for him to get,” the paper wrote.

“He waved at friends, swung his heavy binoculars in a carefree manner and when little Eddie Arcaro rode Lawrin up to the tan-barked, flower-edged plaza and into that magic circle, Mr. Woolf strode forward and gripped the jockey’s hand as if he were a long lost friend.”

The headline the next day in the Kansas City Star said, “It’s Our Derby.” The sub-head was flashier, “Lawrin’s Winged Feet Bring Turf Glory to Herbert Woolf and Kansas City.” Arcaro told the Star he thought Lawrin was better than War Admiral. This was amazing praise in 1938 when War Admiral was half of one of the greatest rivalries in all of sports.

The 1938 Derby was run in a year when horse racing often dominated sports coverage. But neither the Kentucky Derby nor the Preakness nor the Belmont Stakes was the biggest race of that year. That title goes to the one-on-one battle between War Admiral and Seabiscuit. 

The fact that Arcaro would even suggest Lawrin was on par with War Admiral would have been big news in 1938, especially since 40 million people, including President Franklin D. Roosevelt, listened to the Kentucky Derby on radio. 

Eddie Arcaro would go on to become one of the most famous jockeys ever. Lawrin was his first of five Derby winners. Arcaro is the only jockey to win two Triple Crowns. As it happens, Lawrin had no chance at a triple crown. Woolf did not register him for the Preakness or Belmont stakes. 

While there wasn’t much horse racing history or action in Kansas, just across the state line there was plenty of horse track action—action that would lead to the downfall of the political boss of Kansas City and an unexpected connection between Herbert Woolf and Boss Tom Pendergast.

Woolf’s rise to business prominence in Kansas City roughly coincides with the assent of Pendergast as the machine boss in the city. The Woolf family moved their clothing business from Leavenworth to Kansas City in 1879, and opened shop at 5th and Main. 


About that same time, the Pendergasts were creating their political dynasty in the West Bottoms. Herbert would take over Woolf Brothers in 1915, and expand the business into Junction City, Wichita, Dallas, and Memphis. Tom would take over the machine from his brother, Big Jim, in 1925 and expand it into almost every political office in Jackson County and much of Missouri. 

While Woolf loved riding and breeding, Pendergast would turn out to be an inveterate gambler on horses. Pendergast’s addiction was so severe that he and associates opened the Riverside Jockey Club just north of Kansas City in 1928. In one month, Boss Tom lost $600,000 dollars at the track. 

Like most things Boss Tom touched, says Jason Roe from the Kansas City Public Library, the Riverside track was barely legal. Roe has extensively studied the Pendergast era in Kansas City.

“Around 1927, the Supreme Court of the United States issued a ruling that created a loophole for gambling on horse racing where you could make, basically, a donation to breeding horses. It’s somewhat like the loophole that exists today. If you participate in a raffle for charitable purposes that’s not gambling, even though you are buying a ticket and you could win something,” says Rose. “That’s the loophole Pendergast was able to take advantage of to open up the racetrack in Riverside.”

In it’s heyday, upwards of 17,000 people would pack the track for a full day of racing. Pendergast got involved in an insurance kickback scheme to help pay off his huge gambling debt. And indirectly, says Roe, it lead to the death of the Pendergast machine. Boss Tom was indicted for failing to report the income from the kickback scheme to the IRS, the same kind of case that brought down Al Capone.

“It was the accountants who got him in the end,” Roe says. 

Tom Pendergast pleaded guilty to tax evasion in May 1939, and spent 15 months in Leavenworth. His boss days were done. But here’s the unexpected connection between Woolf and Pendergast—after Boss Tom got out of prison he still had five years probation to serve, a common part of any sentence. On Aug. 13, 1943, a letter was sent from the office of federal Judge Merrill E. Otis, the judge who sent Boss Tom up the river. A group of notable Kansas Citians wrote the Justice Department’s pardon attorney asking that Pendergast be released early from his probation. Banker James Kemper wrote a letter. So did developer J.C. Nichols as did Monsignor Thomas McDonald, a prominent priest in Kansas City. Also advocating for Boss Tom: Herbert M. Woolf. 

Did Woolf write because the two had some business connection or political connection? Maybe, it was a horse connection. To this day, nobody knows. 


Our theme music is used in this episode is Shy Touches by Nameless Dancers. Other music used in this episode is Manele, Begrudge, Rally, and Drifting Spade by Blue Dot Sessions; both have been edited.