Primary upper extremity deep venous thrombosis (DVT), or effort thrombosis, typically occurs in young, healthy individuals with a history of repetitive upper extremity movement while secondary upper extremity DVT is associated with a number of predisposing factors. The role of factors such as hypercoagulability in the development of effort thrombosis is less well described. This report describes a previously healthy 21-year-old man who presented with simultaneous bilateral upper extremity DVT after hours of pushing and lifting a heavy wheelbarrow. Treatment included thrombolytic therapy followed by delayed venolysis and vein patch angioplasty. Hypercoagulable screening revealed factor V Leiden heterozygous characteristics.