Private Kweskin did military service February 1943 to December 1945, during World War II, joining the 83rd Chemical Mortar Battalion in September 1944 as a military artist, contributing to the military periodicals "Muzzleblasts" and "Rounds Away". and said he was among the Allied troops who helped liberate the Dachau concentration camp. After his discharge, he studied at the Art Institute of Chicago, receiving a Bachelor of Fine Arts degree in early 1949. He worked for a year with former Walt Disney Pictures animator Sam Singer, doing two children's cartoon series for the local ABC-TV station. Kweskin then left to develop his own local children's-TV programs.