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To report a case of a 79-year-old man who presented a bilateral popliteal artery aneurysm compressing both popliteal veins mimicking signs and symptoms of post-thrombotic syndrome. A 79-year-old male patient, was seen in the ambulatory clinic with a 2-year history of bilateral leg swelling, calf pain, chronic ulceration, and hyperpigmentation. Upon physical examination, lower extremities were edematous, with a 3 cm suppurative ulcer on each leg. Image studies showed a popliteal right arterial aneurysm of maximum diameter of 41.7 mm, e