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Photo Credit: Greg Wood

Events, Missouri History, People

K.C. Gangster Tour

Murder and Mayhem

Our gang took a killer tour!

Bootleggers, jazz, and murder.

Welcome to Kansas City Gangster Tour, where the Roaring 20s and Prohibition still echo off of downtown’s concrete walls. Here, the booze flowed freely, the jazz never stopped, and gangsters ran the town with a mix of style, smarts, and latent danger.

Bada Boom, Bada Bing! Guide Johnny “Aces” Holiday (aka Kelly Rusk) wears a 1920s-style pinstripe suit with black-and-white wingtip oxfords and a fedora, and his sidekick, bus driver Benny the Bull (aka Ben Merricks), welcome visitors to the Kansas City Gangster Tour, run by Kansas City Transportation Group.

Two men in pinstripe suits stand in front of a plain grey background. The shorter man on the left crosses his arms and wears a black cap and red tie. The taller man on the right smiles, gives a thumbs up, and wears a grey fedora and white tie.
• Benny the Bull (left) and Johnny “Aces” Holiday • Greg Wood

They are joined on a TV screen mounted on the bus by a few other characters: Johnny’s girlfriend, Velma, a simpering flapper who calls Johnny “Poopsie,” and Johnny’s older brother Tommy, a colorful character.

The tour hits the hot spots of the time frequented by famous guests. Al Capone, Frank Sinatra, and Liberace hung out at the Rieger Hotel and other swanky hotels. Johnny points out jazz and juice joints, the location where comedian Red Skelton met the woman who would become his wife, and theaters around 12th and Vine Streets, where Count Basie played and Sally Rand performed her scandalous fan dance at the Folly Theater. He highlights a few former brothels.

It was the Roaring 20s, and de- spite Prohibition, which began in 1920 and lasted until 1933, the free-flowing giggle water helped Kansas City earn the name, “Paris of the Plains.” Local mobster and political boss Tom Pendergast made sure the hooch flowed freely at 24-hour jazz joints, speakeasies, and only somewhat secret gambling clubs. Once asked about his flagrant defiance of federal Prohibition laws, Pendergast simply said, “The people are thirsty.”

Two older men in suits are seated and facing each other. One wears round glasses, while the other wears a hat, glasses, and a boutonnière with ribbons. They appear to be having a conversation.
• Senator Harry S. Truman, left, is with Thomas “Boss Tom” Pendergast at the Democratic National Convention in 1936. Boss Tom helped Truman begin his political career.
• Wiki Commons

Johnny’s stories make the gangster tour come alive. He tells how a dancer, Louise Hovick, was stranded in Kansas City when her troupe broke up. Penniless, she put together her first burlesque act and debuted at the Gayety Theater, becoming Gypsy Rose Lee.

Johnny, along with Tommy on the TV screen, relayed how Pendergast had more power than the mayor and many legislators, even helping Harry S. Truman when he entered politics.

Pendergast’s Ready Mixed Concrete Company gave him the gold that funded his power. Johnny reminded us of the alternative golden rule: The one who has the gold makes the rules. Pendergast’s gold came from trucks full of heavy loads of gray, wet concrete.

His company provided the concrete for Jackson County Courthouse, City Hall on 12th Street, Municipal Auditorium, and the Kansas City Police Department Headquarters. He built the Jackson Democratic Club, where he dispensed bribes and controlled county and state politics. He swayed elections so much that some of his candidates won with 95 percent of the vote.

Legend suggests the deep foundations and thick walls around town may contain more than concrete. Capisce? But Fuhgeddaboudit!

What mattered to people was that Boss Tom gave jobs to many Kansas Citians during the Great Depression. In 1931, the city passed a $50 million bond to modernize aging buildings. Pendergast was able to direct money to companies he owned, lining his own pockets while providing jobs.

The tour passes Pendergast’s former home, office, and church, then enters the Armour District, which was a lively urban stretch of apartments, hotels, and nightlife during Prohibition.

End of the line, see! Here, Johnny steps outside the bus to reenact the killing of Johnny Lazia, who was part of Pendergast’s criminal network. Lazia, his wife, and his bodyguard Charles Carrollo arrived at the couple’s residence at the Park Central Hotel on East Armour Boulevard after spending the night touring nightclubs and gambling dens.

As Lazia stepped out of the car, gunmen hiding in the bushes sprayed him with bullets from a submachine gun and sawed-off shotgun. Lazia pushed his wife back into the car and told Carollo to drive away. They escaped, and Carollo replaced Lazia as one of the bosses under Pendergast.

Seven adults stand in a row outdoors against a stone wall, smiling and posing with thumbs up and finger guns. One man wears a pinstripe suit and hat; others are dressed casually in shorts, shirts, or jackets.
• From left, Greg Wood, Jonathan and Charlene Finck, our guide Kelly Rusk, Danita Allen Wood, and Nina and Terry Furstenau ham it up. Nina points at a bullet hole at Union Station. • Ben Merricks

The Kansas City Massacre

The tour ends where it began, at Kansas City’s Union Station, where Johnny shows us bullet holes in the concrete walls of the station. The most shocking gangland murders during Prohibition took place here on June 17, 1933, in broad daylight.

Law officers were moving Frank Nash, a convicted murderer, from Arkansas back to the US Penitentiary at Leavenworth, Kansas, from which he had escaped in 1930. His friends, gangsters Charles Arthur “Pretty Boy” Floyd, Vernon Miller, and Adam Richetti, had learned of his arrest and plotted to free him at the station, where he was to be transferred from the train to a car to finish the journey to Leavenworth.

As the lawmen escorted Nash toward the car outside the station, either four or five gangsters (it has never been determined for sure) opened fire with shotguns and automatic weapons. The gunplay lasted only about 30 seconds to a minute, but it resulted in the deaths of two Kansas City policemen, one county sheriff, and one federal government agent. Nash was also killed in the crossfire.

The horrific event gave the Bureau of Investigation, which later became the Federal Bureau of Investigation, expanded powers, as they were soon formally allowed to carry firearms and make arrests. It remains one of the most infamous moments in the Kansas City gangster era and marks the beginning of the end of the Midwest’s wide-open mob years.

1300 Lydia Avenue, Kansas City KansasCityTransportationGroup.com • Call 816-471-1234 to make reservations.


This article was orginally published in the May 2026 issue of Missouri Life.

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