Clear-cell chondrosarcoma is a rare, low-grade variant of chondrosarcoma characterized by slow growth, low metastatic potential, and a predilection for local recurrence long after treatment. We report an unusually aggressive case of clear-cell chondrosarcoma of the humerus with early metastasis to multiple bony sites including femur, thoracic and lumbar spine, sacrum, and iliac bone. Our purpose is to alert physicians to the sarcoma's potential for aggressive behavior, necessitating closer and more frequent followups for early detection and treatment of tumor recurrence and metastasis. We also review the reported imaging and histological features, which may help identify aggressive cases.