Coronavirus disease (COVID-19) pandemic has rapidly spread around the world. As new complications associated with the virus become more apparent, concerns in the medical community continue to grow. One of the more commonly encountered and more troubling complications in critically ill patients has been hypercoagulable state and subsequent thrombotic events. Within the spectrum of observed thrombotic events, pulmonary embolism seems to prevail. These trends are concerning and reinforce current recommendations on anticoagulation in critically ill with the virus. To illustrate the variety of possible presentations of pulmonary emboli in COVID-19 population, two cases of patients in their sixties are described, one without any predisposing risk factors and one with history of asthma and obesity. These patients developed pulmonary emboli at different points during their hospital course, were treated differently, and had different outcomes. Important observations are made that may shed some light on possible etiology of pulmonary emboli. One of the patients presented still developed pulmonary embolism despite being on full dose anticoagulation. Literature review suggests that pulmonary clot burden in COVID-19 patients could be due to pulmonary thrombus rather than pulmonary embolism and is triggered by profuse vascular damage and severe inflammatory response. Literature review also proposes changes to the diagnostic work up in COVID-19 patients, such as earlier screening for pulmonary embolism in critically ill. In addition, rare and severe complications of current anticoagulation therapy is illustrated and discussed through one of the cases presented.