Acute aortic dissection is often a fatal condition with in-hospital mortality rates of 27%. The incidence of acute aortic dissection is low at around 3 cases per 100,000 person-years. There is a strong relationship between hypertension and aortic dissection. 72% of patients in the International Registry of Acute Aortic Dissection had a history of hypertension. The inciting event is an intimal tear extending into the media with resultant dissection of blood along the laminar planes of the media. Cisplatin, a commonly used platinum-based chemotherapy drug, is associated with the development of hypertension on long-term follow up studies. This knowledge should prompt clinicians to screen for the development of hypertension and to be aware of its potential complications in patients treated with cisplatin-containing chemotherapy. Despite the known vascular complications of chemotherapy, there is a paucity of data on the association of aortic dissection with active cancer or chemotherapy. We present an unusual case of an extensive, acute aortic dissection in a relatively young male patient receiving gemcitabine and cisplatin for advanced metastatic pancreatic adenocarcinoma.