Multiple primary tumors are rare, with a published meta-analysis that shows the frequency of second primary tumor at 3-5%, and a third tumor at 0.5%. A 57-year-old female sought consultation due to a persistently bleeding right nasolabial mass. On further history and examination, she also presented with a right anterior neck mass, repeated abortions, secondary amenorrhea, and loss of libido years prior. Serum prolactin was significantly elevated and an incidental finding of a pituitary mass on head and neck CT scan was appreciated. Metastasis and syndromic familial disorder were ruled out. Bromocriptine was given and she underwent total thyroidectomy and wide excision of the right nasolabial mass which turned out to be papillary thyroid carcinoma (PTC) and basal cell carcinoma (BCC) respectively on histopathologic report. On follow up, repeat serum prolactin decreased to normal levels. After extensive literature review, this is the first documented case of triple synchronous tumors with a combination of BCC of the right nasolabial area, PTC and prolactinoma in local, national and international studies. With comprehensive work up and literature search, the diagnosis was established and ultimately the patient benefited from a multidisciplinary management.