Anomalous origin of the left main coronary trunk from the right coronary sinus is a rare condition and is associated with a significantly increased risk of cardiac events, including sudden cardiac death, and it may pose difficulties in their management using revascularization strategies. We present a case of a 68-year-old man with worsening chest pain. Initial evaluation revealed ST elevation of the inferior wall leads and elevated troponins. He was diagnosed with ST-elevation myocardial infarction (STEMI) and sent for emergency cardiac catheterization. Coronary angiography showed 50% stenosis of the mid-right coronary artery (RCA) that extended as a total occlusion to the distal RCA and an unexpected anomalous origin of the left main coronary artery (LMCA). Our patient's LMCA originated from the right cusp sharing a single ostium with the RCA. Multiple attempts of revascularization with percutaneous coronary intervention (PCI), using multiple wires, catheters, and different-sized balloons, were unsuccessful due to complex anatomy. Our patient was managed with medical therapy and discharged home with close cardiology follow-up.