Siemaszko was born in Chicago and grew up on the city's northwest side. He attended Saint Ignatius College Preparatory School and graduated from the Goodman School of Drama at DePaul University in 1983. His father, Konstanty (1918-1999), was a Polish Roman Catholic and a former member of the Polish Navy. He joined the Polish Underground and was a survivor of the Sachsenhausen concentration camp. He immigrated to Chicago in 1959 and became a well-known local choreographer and a fixture in the Polish community. His mother, Collette McAllister (1931-2008), was English. His sister Nina is an actress and his brother, Corky, is a writer for Daily News and a reporter for NBC News.
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