About Kansas City’s Wild Jazz Club, The Chesterfield Club

It was the wild, raucous “anything goes” heyday of Kansas City, Missouri in the 1920s – 40s. Jazz flowed as freely as the booze, even during prohibition, and the many downtown clubs offered gambling, sex and drugs — so long as everybody paid Boss Pendergast. 

Among the many famous and infamous bars & establishments, The Chesterfield Club shined one of the brightest. Perhaps because it was owned and operated by notorious mobster Frank Costello of the Luciano crime family.

“The Chesterfield Club was not the only hot night-spot in town,” wrote one author. “It was just the only one that happened to offer nude waitresses with the noon meal.”

The club operated from 1927 to 1941 at the corner of 23rd and Vine Street — the epicenter of the city’s jazz heyday.

In turn, the club was famous for its long jam sessions that gave birth to the bebop movement. Known for its luxurious atmosphere, high‑quality sound, and eclectic lineup of performers, Chesterfield Club was a hotspot for both locals and visitors—especially African American jazz enthusiasts.

In KC’s notorious clubs, you could find Charlie Parker discovering the foundation of Jazz, and Big Joe Turner inventing the framework of Rock n Roll. It was in this time Count Basie formed his landmark band in KC after coming to town for a gig — and ending up stranded & homeless when it fell through. 

When the authorities finally broke up Pendergast’s tight-fisted empire, the mafia, needing to continue their source of gambling income, hatched a plan to move casino operations to the tiny Nevada Desert town of Las Vegas…