The objective of this case study is to discuss a rare case of proven paradoxical thromboembolism captured in-transit. A 23-year-old female with a diagnosis of right internal jugular deep vein thrombus who developed acute onset chest pain, dyspnea and hypotension, was selected for the study. Sub-massive PE and STEMI were diagnosed. Transthoracic echocardiogram revealed a left ventricular (LV) mass moving across the aortic valve. Soon after, the patient developed numbness of right extremities with non-palpable pulses. A transesophageal echocardiogram revealed absent LV mass, PFO, left atrial mass entering through the PFO and emboli in bilateral pulmonary arteries. We report a case of sub-massive PE and paradoxical proven coronary and upper extremity embolism, captured in-transit, following destabilization of an UEDVT in a patient with PFO.