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ONE OF THE AMERICA'S most powerful and influential labor leaders, Sidney Hillman cofounded the Congress of Industrial Organizations (CIO), which later merged with the American Federation of Labor (AFL) and mobilized its members into the first truly effective labor force in electoral politics. He was also one of the earliest trade-union advocates of constructive cooperation, recognizing that what helped an industry's workers benefited the industry itself. He was also a close confidante of President Franklin D. Roosevelt (FDR)—to the point where Hillman himself became a major issue during the 1944 presidential campaign, inspiring one of the most famous controversies, and slogans, in U.S. political history.

Born in Lithuania, Hillman abandoned rabbinical studies for a role in the struggle against Tzarist oppression: He took part in the abortive 1905 Russian revolution and was imprisoned for six months, freed in a general amnesty, then jailed again. Eventually released, he decided to leave Russia, immigrating first to England and then to the United States, where he arrived in 1907. Two years later, he began working in the men's clothing industry, where he organized an unsuccessful strike. Hillman persevered and eventually created a landmark series of cooperative agreements that provided for arbitration procedures; by 1914, he'd been named the first president of the Amalgamated Clothing Workers Union, a position he held for the rest of his life. While walking his first picket line, he met a young striker named Bessie Abramowitz, and they were married in 1916; she also became vice president of the union, whose membership rolls had reached 400,000 by the time of Hillman's death.

In 1935, Hillman took his union out of the AFL and joined with John L. Lewis to form the CIO, becoming Lewis's right-hand man and first vice president. There, he played a key role in organizing the steel and automobile industries, all with his trademark of avoiding violence and confrontation as much as possible. He and Lewis were often at odds, however, particularly over a merger with the AFL, which Hillman strongly favored. During the late 1930s, FDR turned to Hillman to represent the national mobilization in the face of the threat of war in Europe. His task was to keep the machinery of industry moving by using his influence to settle disputes and avert strikes and job walk-offs. He was successful enough that Roosevelt, in 1940, named him associate director of the Office of Production Management.

During the war, Hillman assumed control of the CIO's political action committee (CIO-PAC), which became a potent force aiding Democratic candidates and led to the controversy that increased his notoriety. When New York Times columnist Arthur Krock wrote that Roosevelt, in discussing the 1944 vice presidential nomination, had told a top aide to “Clear it with Sidney,” a Republican campaign slogan was born, though it proved insufficient to defeat the president.

Adding to the controversy was Hillman's newfound willingness to work closely with communist-dominated unions. Though he had long fought communist attempts to take over his own union, Hillman reasoned that as the United States and Soviet Union were wartime allies, the latter's labor sympathizers should be encouraged to participate fully in the war effort. But Hillman moved from cooperation to outright advocacy: In 1944, communist and anti-communist factions, the latter led by David Dubinsky and Alex Rose, battled for control of the far-left American Labor Party, and Hillman interceded on behalf of the pro-communist unions, which won out. The losers then quit the ALP, which eventually disintegrated, and formed the New York State Liberal Party.

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