Siemaszko was born in Chicago, Illinois. His father, Konstanty (died 1999), was a Polish-born Roman Catholic who was a fighter in the Polish Underground during World War II, and who survived the Sachsenhausen concentration camp. His mother, Collette McAllister (1931-2008), was from the United Kingdom. Siemaszko narrated the 1998 feature, The Polish-Americans. He is a graduate of The Theatre School at DePaul University in Chicago, as is his sister, actress Nina Siemaszko. He also has a brother, Corky Siemaszko, who previously worked as a reporter/writer for the New York Daily News and currently works as a reporter for NBC News.
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