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Chronic lymphedema is rarely complicated by an angiosarcoma. Angiosarcoma superimposed on chronic lymphedema (Stewart–Treves syndrome) is usually seen post breast cancer surgery accompanied by lymph node resection of the axilla. This is a case report of a 59-year-old male patient with elephantiasis that developed an angiosarcoma of the lower leg. He died a month after the diagnostic biopsy was obtained. This is a rare multifocal tumor in a male with an unusual lower leg location. We reviewed the literature and the need to differentiate this often deadly lesion from a Kaposi’s sarcoma.