Milton Woolf was born in New York City in 1915. During the Great Depression Woolf joined the Civilian Conservation Corps. His experiences of the gap between rich and poor "disillusioned and abused and enlightened" him. On returning to Brooklyn he joined the Young Communist League.
Woolf arrived in Spain in March 1937. As he was a pacifist he initially wanted to be a medic but was later persuaded to become a machine-gunner with the George Washington Battalion. He fought in the battles at Brunete, Belchite and Teruel.
The American forces suffered heavy casualties in the war. In March 1938 the Lincoln-Washington Battalion lost two of its most senior officers, Robert Merriman and David Doran, when they were killed at Gandesa on the Aragón front. Wolff now assumed command of the battalion and John Gates became battalion commissar. Woolf led his forces at the great offensive across the River Ebro on the 25th July 1938. The men then moved forward towards Corbera and Gandesa.
On 26th July the Republican Army attempted to capture Hill 481, a key position at Gandesa. Hill 481 was well protected with barbed wire, trenches and bunkers. The Republicans suffered heavy casualties and after six days was forced to retreat to Hill 666 on the Sierra Pandols. It successfully defended the hill from a Nationalist offensive in September but once again large numbers were killed.
The head of the Republican government, Juan Negrin, announced on 21st September that the International Brigades would be unilaterally withdrawn from Spain. That night the Lincoln-Washington Battalion moved back across the River Ebro and began their journey out of the country.
In the Second World War Woolf joined the United States Army and served in Italy and Burma. General William Donovan recruited him into the Office of Strategic Services, and served with the "British Special Services after the fall of Paris and the Nazi invasion of Yugoslavia." He told Studs Terkel: "I don't ever want to see another bloody war again. There's a certain amount of glamour attached to a guy like me because I was a warrior. But I've always had more respect for the conscientious objectors. We were in good wars, that's what we should be honored for, but not because we were warriors."
On his return to the United States he became involved in the civil rights movement. His friend, Alvah Bessie, pointed out: "Wolff himself served as National Commander of the Veterans for many years after the war, working also with the Civil Rights Congress and every committee set up to aid Spanish refugees or political prisoners. He was the sparkplug of VALB's campaign to keep fascist Spain out of the United Nations during 1946-48, and he was involved in the Willie McGee case in Jackson, Mississippi, touring the south before the Freedom Marchers were organized, helping save the lives of the Martinsville Seven and raising $2,000,000 in bail money for Smith Act victims and helping to save the XVth Brigade's commissar Steve Nelson from literal death in a Pittsburgh dungeon."