Acute aortic dissection (AD) involves the tearing of the aortic intima by shearing forces, resulting in a false lumen, which, depending on its location and extent, may lead to hemodynamic compromise, hypoperfusion of vital organs, or even rupture of the aorta. The classical presentation is a sudden chest or back pain described as sharp or ripping in quality. We present a 60-year-old male with a history of hypertension, Liddle’s syndrome, obstructive sleep apnea, and chronic cannabis use for insomnia who arrived at a non-PCI hospital complaining of severe retrosternal chest pain lasting several hours in evolution that started upon masturbation. The pain was ripping in character, starting retrosternally and radiating to his neck and back. After evidence of rising troponin values, he was initially diagnosed with non-ST segment elevation myocardial infarction (NSTEMI), managed with dual antiplatelet therapy with full anticoagulation, and subsequently transferred to our institution for further care. Shortly after his arrival at our hospital, he suddenly deteriorated with recurrent chest pain and hypotension, which triggered an emergent bedside echocardiogram evaluation. This revealed a hemodynamically significant pericardial effusion, moderate to severe aortic valve regurgitation (AR), and an intimal flap visualized on the ascending and descending aorta, suggestive of an extensive AD. A computerized tomographic angiogram confirmed the diagnosis of a Stanford type A AD that required an emergent surgical pericardiotomy, ascending aorta with partial arch replacement, and aortic valve repair. Often, AD may mimic an acute coronary syndrome (ACS) or even present with an acute myocardial infarction (AMI). The appropriate diagnostic imaging evaluation prior to the initiation of anticoagulation therapy should be done in patients with higher-risk clinical criteria for AD to reduce adverse treatment outcomes. The use of a simple three-step diagnostic algorithm for acute aortic syndromes (AAS) may decrease diagnostic delays, misdiagnosis, and inappropriate therapies.