Merkel cell carcinoma (MCC) is an uncommon highly aggressive skin malignancy with an increased tendency to recur locally, invade regional lymph nodes, and metastasize distally to lung, liver, brain, bone, and skin. The sun-exposed skin of head and neck is the most frequent site of involvement (55%). We report the case of a 63-year-old Caucasian male patient who presented with a recurrent left inguinal mass for the third time after surgical resection with safe margins and no postoperative radio- or chemotherapy. The presented mass was excised, and pathological diagnosis revealed recurrent MCC. The patient underwent postoperative radiation therapy, and 6 months later, he developed a right groin mass which was resected and pathological diagnosis confirmed metastatic MCC. Six months later, patient developed an oropharyngeal mass which was unresectable, and pathological biopsy confirmed metastatic MCC. Patient was offered palliative radio- and chemotherapy. In this paper, we also present a brief literature review on MCC.