Long before Teddy Kollek became mayor of Jerusalem, he was a gunrunner for the Yishuv, the Jewish community of pre-State Israel. When it became clear that the British would withdraw from Palestine and a war between the Jews and Arabs over Israel’s independence was inevitable, the Jews would need arms in order to survive. The U.S. was awash with weapons, surplus from World War II, but the 1935 Neutrality Act, prohibited the exportation of military equipment to Israel. All armaments would have to be acquired illegally and smuggled out of America. Those involved would be criminals under U.S. law. In October 1947, the Haganah, the Yishuv’s clandestine paramilitary organization, dispatched Kollek to New York to head their illegal arms procurement mission.
The offices of the Haganah in New York were located in the upper floors of Manhattan’s Hotel Fourteen a somewhat seedy hotel, whose basement was rented out to the Copacabana nightclub. The nightspot was noted for its Copa Girls, a chorus line of young ladies wearing only a bit of fake fruit to cover strategic parts. Famous entertainers of the day performed at the Copacabana, which was owned by members of the Italian Mafia. By day, the Haganah operatives went about their surreptitious activities in the hotel above and by night, they hobnobbed with entertainers and mobsters in the Copa below.
In March 1948, Teddy Kollek had a problem. Docked at the Port of New York, he had an Irish ship captain at the helm of a boat full of arms purchased by the Haganah. The boat with fake bills of lading was to sail beyond the three-mile territorial limit of the U.S., outside the jurisdiction of American authorities and off-load its cargo of munitions onto another ship destined for Israel. The boat, however, was going nowhere until the captain received his bribe, which Kollek was carrying in a satchel laden with cash, reportedly about $1 million. But, Kollek fearing he was being watched by the FBI had no way to deliver the cash to the captain.
Kollek went downstairs to the Copacabana where Frank Sinatra was performing. He and Sinatra had met before. Kollek was sitting at the bar when Sinatra came over and the two struck up a conversation. Kollek could not explain why, but for some reason he confided in Sinatra the reason he was in New York and his dilemma. In the early hours of the morning, Kollek left the Copa through the front entrance, satchel in hand and sure enough, the FBI tailed him. Meanwhile Sinatra left the nightclub through a back door carrying a paper bag, travelled to the pier, handed the bag filled with Kollek’s cash to the captain and watched the boat sail. Had Sinatra been caught, he would have faced jail time and the end of his singing career.