Inflammatory myofibroblastic tumor and liposarcoma very rarely present as tumors of the chest wall. Never have both been reported together in the same lesion. We present a case wherein a 72-year-old man with a rapidly progressing lesion initially mistaken for a local infection underwent resection with diagnosis of inflammatory myofibroblastic tumor. He experienced recurrence less than 6 months before radical resection revealed well to dedifferentiated liposarcoma with areas of inflammatory myofibroblastic tumor. He is now doing well with over 4 years of follow-up.