A pulmonary embolism (PE) that is located in the main pulmonary artery is known as a saddle pulmonary embolism. Individuals at high risk who become unstable often require surgical intervention or more aggressive management with thrombolytic therapy. COVID-19 is a known risk factor for a hypercoagulable state and therefore increases the risk of PE and its associated complications. Individuals hospitalized with the COVID-19 virus and who have evidence of right ventricular dysfunction with PE are found to have a significantly higher risk of mortality. We present a case of an individual with several high-risk factors for PE as well as COVID-19 infection and evidence of cardiac strain, making the decision for treatment less clear. He was, however, treated successfully with heparin and enoxaparin alone. Furthermore, our case had resolving symptoms of COVID-19, highlighting the importance of high clinical suspicion for PE in those diagnosed with COVID-19.