On May 22, 1955, an era in Boston nightlife ended when the Latin Quarter closed its doors for the last time.

The Latin Quarter (46 Winchester Street) packed a lot of nightlife history into its 16-plus years. None were more fascinating than its last chapter, from October 1952 to May 1955. That was the era of Rocco “Rocky” Palladino, a character with a cloudy past, a stable of race horses, and a history of run-ins with the Boston Licensing Board.

Photo of Christine Jorgensen

Christine Jorgensen: The Boston Licensing Board had it in for her

The BLB forced Palladino to close another of his clubs, the College Inn, for putting female impersonators on stage in 1952. That was illegal in Boston, and had been since 1948. I’m sure the BLB was less than pleased to see Palladino back in action at the Latin Quarter.

The Latin Quarter was not a jazz club but the previous owners had booked jazz artists with crossover appeal. Palladino, though, had a special fondness for the Italian-American boy singers who rose to prominence in the 1950s, such as Tony Bennett, Tony Martin, Al Martino, and Jerry Vale. In January 1953, Palladino brought in Frank Sinatra, the biggest Italian-American boy singer of all, in what was his only Boston nightclub appearance as a single.

It came apart for the Latin Quarter a year later with l’affaire Christine. Palladino booked Christine Jorgensen for a week in February 1954. Ms. Jorgensen was much celebrated because of her sex-change operation, and she was touring with a low-key nightclub act. Mary Driscoll, chair of the Boston Licensing Board, said she’d “move heaven and earth” to prevent the show on the grounds that Jorgensen was a female impersonator. Upon being told Jorgensen wasn’t impersonating anybody, the Boston City Council passed an order essentially forcing Jorgensen to submit to a medical examination. Jorgensen sued. Driscoll backed off, saying she was “misinformed.” The show, apparently, could go on.

Driscoll’s board then suspended the Latin Quarter’s operating license for the duration of the show, blocking Jorgensen’s appearance. After ten days, they lifted the suspension and business resumed for Billy Eckstine, Nat Cole, Sammy Davis, Jr. and others. But the Licensing Board continued to hound Palladino.

In May 1955, Eartha Kitt opened for a week, accompanied by a good band: Perry Lopez, guitar, Al Escobar, piano, Gene Ramey, bass, and Denzil Best, drums. After she closed on May 22, the word went out that the club was closed effective immediately. Even the employees were caught by surprise.

It wasn’t the Licensing Board’s war with Palladino that brought the closure, it was the changing economics of entertainment. The Latin Quarter could no longer compete for the big names that were its stock in trade. To afford the escalating salaries, the Latin Quarter raised its prices, and the public was chafing. Only two years before, Frank Sinatra played the club with no cover charge, even on weekends, and that was impossible in 1955. But the barn-like Blinstrub’s, with seating for well over 1,000 in 1955, could afford to pay the big stars without constantly raising the prices it charged its customers—they made it up on volume. The Latin Quarter didn’t have the volume. “There was no compromise with quality at the Latin Quarter right up to the end,” wrote George Clarke in the Record. “There just wasn’t enough money coming in.”

It’s a lament Boston heard again when the doors closed for the last time at Storyville five years later, and at the Jazz Workshop a few decades later. There just wasn’t enough money coming in.