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Sheriff Finn wangled De Sapio a job as secretary to City Judge Vincent S. Lippe at $3,500 a year, and that put De Sapio in a position to marry Theresa Natale (her friends call her Tess, her husband calls her "Girlie"), a pretty secretary from Hoboken whom he had met at a dance several years before. By now, De Sapio was obviously a rising young pol, and Sheriff Finn, a pallid imitation of tough old Battery Dan, was on the skids. In 1939, egged on by Huronites dissatisfied with Finn's sorry leadership, De Sapio founded his own Tamawa Club (he made up the name, thinking it sounded properly Indianish) and stood against Finn for district leader. He was elected.
This was unforgivable. "In those days," recalls De Sapio bitterly, "the Irish leaders used to give the Italians important-sounding jobs—without power—to keep them happy; something with a nice fancy-sounding title, like Superintendent of Sanitation, that an Italian would love." But district leader? Never. Tammany's executive committee refused to seat De Sapio. When De Sapio's followers picketed both the hall and Finn's office, Finn cried foul. "It's in line with all the tactics they've been using," he said. Then, darkly: "I might even say it smells strongly of Communism."
De Sapio fought Finn for district leader again in 1941, won again, and was again refused Tammany's recognition. In 1943, with another De Sapio victory, the Tammany sachems at last gave in (partly because Finn had become involved in a factional dispute with Tammany Leader Mike Kennedy). That year De Sapio took his place on the Tammany Hall executive committee. Within six years he was the Boss.
"I Gotta Go On." His rapid ascension came partly because Tammany was torn by factionalism, partly because of his capacity for work and his attention to political details, partly because the late Bronx Leader Ed Flynn, the real power in New York politics during Tammany's dog days, spotted De Sapio as a comer. Says Julie McArdle, who was Flynn's secretary for 20 years and is now De Sapio's: "I remember Mr. Flynn saying Mr. De Sapio was the only Tammany leader he could sit down with since Mr. Murphy, and not have to talk out of the side of his mouth.'' Flynn advised De Sapio, brought him along, and was delighted to see him made leader of Manhattan, the borough just south of Flynn's Bronx.
But for all Ed Flynn's influence, he could not make De Sapio's position secure. Beneath De Sapio's shaky perch slavered a whole litter of lesser tigers just waiting for him to make his first slip. He slipped, and soon. With Flynn, he supported Judge Ferdinand Pecora, an honest man cursed with every outward attribute of the typical Tammany stooge, against a Tammany outcast. Vincent Impellitteri, who looked to the voters like a brave little David slinging stones at a Goliath. "Impy," without machine support, won easily. Never had Tammany Hall suffered a more galling defeat. De Sapio was on the way out; at one point he managed to hold on by only two committee votes.