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Leonard Woodcock began his career as a union leader in 1933. During the hard times of the Great Depression, he went to work at Borg-Warner Corporation’s Detroit Gear and Machine Division. There, Woodcock joined AFL Federal Local Union 18564, which became Local 42 at the 1936 UAW Convention. Like most industrial workers during this era, Woodcock encountered low pay, poor working conditions, and a general lack of dignity. For the rest of his life, he worked toward economic and social justice for all working people.

In 1939, Woodcock began to make his mark as a labor activist. As the educational director of the Wayne County CIO Council, he conducted classes on union organizing and administration. During this era, Woodcock also became an associate of Walter Reuther. After a stint as a representative for UAW Region 1D, he held a wartime job as a punch press operator in Muskegon, Michigan. When Reuther became president of the UAW in 1946, Woodcock became his first administrative assistant.