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We report herein a unique case of an adenosquamous carcinoma (ASC) of the pancreas and a synchronous gastrointestinal stromal tumor (GIST) of stomach in a 75-year-old Caucasian male. He presented with painless jaundice and generalized pruritus and was found to have a pancreatic head mass. Whipple's procedure was performed and yielded the above diagnoses. Ductal pancreatic adenocarcinoma, not a much rarer and more aggressive ASC subtype, has previously been shown to co-exist with GIST in some surgical series. In addition, the incidentally discovered GIST in our patient involved the stomach and not the small intestine, which is the predominant GIST location when concurrently diagnosed with other GI tumors. At the time of this publication, our patient, who received adjuvant chemoradiotherapy, remains disease-free 14 months after the abdominal surgery.