The hottest female nightclub star in 1930s Havana guards two secrets: She is a Polish-born American Jew, and she has a penis. Lola Flores, a musically gifted transgender woman, lives in constant fear of discovery while battling inner demons. Days before the 1929 Wall Street crash, 19-year-old pianist Albert Sobel fakes drowning in New York's East River. As Lola Torres, she rides the Havana Special to Key West only to be assaulted by the train's conductor. In politically unstable Havana, a Jewish nightclub proprietress tied to the American mob offers Lola a job. A transgender man, Fernando Fallon, designs her trademark floral hat and becomes her lifelong platonic companion. Lola is preyed on by the nightclub owner then a senior government official. The notorious gangster Ben "Bugsy" Siegel, unaware she is trans, takes her under his wing. In Nazi Berlin with bandleader Xavier Cugat, Lola meets the ill-fated transgender Danish woman Lili Elbe. Revolution in Cuba drives Lola back to New York. Depression-era Broadway brings a role in The Ziegfeld Follies of 1936, support by columnist Walter Winchell and spying in Havana for the FBI. World War Two Hollywood produces a glittering but brief film career, a tragic love affair and a hushed reunion with a sister. After Siegel's 1947 murder in Los Angeles, Lola and Fernando flee to San Francisco. There they meet Christine Jorgensen, the first woman to successfully undergo gender reassignment. In 1953, Lola confronts McCarthyism while defending friend Lucille Ball from charges of Communist activity. On the set of I Love Lucy in 1954, Lola collapses. Dying, she recalls arriving in New York Harbor at age two and her father's ironic words.