Lung cancer can lead to hypercoagulability that causes thromboembolic events such as pulmonary emboli, deep vein thrombosis, ischemic strokes, and non-bacterial thrombotic endocarditis. While it is not uncommon for cancer to cause thromboembolic events, it is unusual for thrombotic events to be the first manifestation of cancer. In the following report, we review the case of a 59-year-old woman who presented with melena and abdominal pain. She had a pertinent history of multiple thromboembolisms while on anticoagulation four months before this presentation. Upon admission, it was discovered that the patient had new pulmonary emboli, and further workup revealed that her gastrointestinal symptoms were due to ischemic colitis. While initial imaging showed no evident masses that would heighten suspicion of cancer, she had persistent abdominal lymphadenopathy. Therefore, she also underwent an abdominal lymph node biopsy which revealed metastatic lung adenocarcinoma, a possible cause of her hypercoagulable state. This case report highlights the importance of considering malignancy in the differential of a patient with recurrent thromboembolism and raises the question of whether standardized screening for malignancy in patients with multiple thromboembolic events would be beneficial.