The coronavirus disease 2019 (COVID-19) has been associated with a prothrombotic state during active infection with the severe acute respiratory syndrome coronavirus (SARS-CoV-2). However, reports of delayed multisystemic COVID-19-associated thromboembolic sequelae are limited in the current literature. In addition, the initiation of prophylactic antithrombotic therapy in patients for the prevention of such events during and after infection remains controversial due to conflicting reports. Here, we present evidence to support that patients with comorbid conditions are at higher risk for multisystemic COVID-19-associated thromboembolic events and propose that beginning prophylactic therapy in this population could lead to more favorable outcomes. We describe a 67-year-old male who presented with left-sided weakness and worsening shortness of breath and was diagnosed with COVID-19 approximately one month prior. Initial computed tomography (CT) of the brain showed an age-indeterminate cerebellar infarct. On CT angiography (CTA) of the neck, a saddle embolus was incidentally found and was confirmed on an immediate follow-up chest CT. After consultation with neurology, a decision was made to administer thrombolytics at the standard recommended stroke dosing. The patient was admitted to the ICU and received mechanical thrombectomy two days later. At the time of hospital discharge, the patient still had left-sided weakness on examination and required no additional oxygen support. This report reviews the prevalence of delayed sequelae of COVID-19 and the benefit of prophylactic antithrombotic therapy during active and post-SARS-CoV-2 infection. It is important for emergency medicine physicians to recognize that patients who have recovered from COVID-19 are at high risk for delayed thromboembolic disease, even in the absence of personal or family history of coagulopathy. This underscores the necessity of obtaining imaging studies in high-risk patients who present with acute symptoms that cannot be explained by other probable causes. In addition, patients should be encouraged to follow up with their primary care providers to discuss prophylactic anticoagulation therapy as it could be beneficial during and post-COVID-19.