A shekara ta 1951, shi da matarsa sun sayi karamin gonar inda daga baya suka gina gida kuma suka haifi 'ya'ya biyu. A shekara ta 1972, Winters ya shiga kasuwanci don kansa, ya fara kamfaninsa kuma ya sayar da kayayyakin abincin dabbobi ga manoma a duk faɗin Pennsylvania. Ba da daɗewa ba bayan haka, ya koma iyalinsa zuwa Hershey, Pennsylvania. Ya yi ritaya a shekara ta 1997. A cikin shekarun 1990, Winters ya fito a cikin littattafai da jerin shirye-shiryen talabijin game da abubuwan da ya samu da na maza a Easy Company. A shekara ta 1992, Stephen Ambrose ya rubuta littafin Band of Brothers: Easy Company, 506th Regiment, 101st Airborne from Normandy to Hitler's Eagle's Nest, wanda daga baya ya zama mai kula da samar da kayayyaki na HBO tare da Damian Lewis.
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