Sam Winn was born Samuel Winokur in rural western Ukraine in 1903. At the age of nine he moved with his family to the town of Lyubar (between Kiev and Lvov), where he received a rudimentary education. His father emigrated to the United States with the intention of saving money so the rest of the family could follow. The plan for emigration was interrupted by World War I and young Sam began to work as a rural laborer in the harvests and soon developed strong leadership skills. In 1919, with the Ukraine ravaged by civil war and anti-Semitic pogroms, he led a group of immigrants from Lyubar to Warsaw, where he was able to make contact with his father. With the help of the Hebrew Immigrant Aid Society (H.I.A.S.), Sam and his family finally traveled to the United States.

Winn lived briefly in New York City, on the Lower East Side, before joining his family in Boston, where he went to high school. He eventually became an apprentice paperhanger and met his wife-to-be, Esther Berowitz, herself an immigrant from the Ukraine and an activist in the shoe-workers union. It was in Boston that Sam became politically aware and a labor activist, first as a member of Paperhangers= Local Union 258 and then as an organizer for the United Textile Workers in northern New England. When the Depression hit, he became active in the Unemployed Councils, was an organizer of the 1931 Hunger March in the Boston area and later worked for the Congress of Industrial Organizations (C.I.O.)

In 1935, Winn moved to New York to help the effort led by Louis Weinstock to gain control of the International Brotherhood of Painters' District Council 9 from the racketeer-linked AZausner Gang.@ For the next four decades, Sam Winn was a leader of the Rank and File Painters= Club of DC 9; he edited club the newspaper and wrote many of its flyers and leaflets. During the Weinstock era, he was a member of the leadership group within DC 9, a frequent delegate to national conventions (including the infamous 1937 Buffalo General Assembly, where he was an outspoken challenger of the national leadership) and an organizer for the war effort during World War II. During Martin Rarback=s tenure as District 9 secretary-treasurer (1947-1966), Winn was an outspoken leader of the opposition for two decades. He played an important role in Rarback=s ouster and trial, and was a frequent target of Rarback=s attacks, which failed to oust Winn in 1953, but succeeded in a trumped-up case in 1962. Winn was also an important supporter of Frank Schonfeld, reform leader in DC 9, and a key organizer of the alliance that brought Schonfeld victory over Rarback and sustained him in office. Sam Winn continued to play an active role in the life of DC 9 after the Schonfeld era as a leader of the opposition to District secretary-treasurer James Bishop.

For over four decades, Sam Winn was also a leading member of Local 490, the Paperhangers= Local within DC 9. He was business agent for two decades (beginning in 1942) and at other times chair, council delegate and trustee of Local 490, as well as the local union=s delegate to the New York Central Trades Council and to numerous state, regional and national meetings of the Brotherhood and of the AFL-CIO. Winn also played a leading role in the creation of the Eastern Seaboard Paperhangers Conference during the 1950s, serving as its Secretary. One of its goals was the establishment of a Paperhangers Department within the Brotherhood, with Winn as its likely head. Before that could happen, DC 9 president Martin Rarback was able to bring him up on charges, oust Winn as business agent and deprive him of his union rights. Although this case was reversed on judicial appeal, it upset the trajectory of Winn's career as a union officer. He returned to work as a paperhanger, but suffered a vocational injury that made it difficult for him to work.

Sam Winn retired from work in 1968, but remained an active member of Local 490 and DC 9 until his death in 1978. He devoted much of the last decade of his life to establishing a credit union within DC 9, and served as its Treasurer until his death from cancer at age 75.