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The proximal humerus is a well-known site of predilection for the solitary osteochondroma—the most common benign bone tumor. Subscapularis tears were underreported in the pre-arthroscopic era. Literature about rotator cuff impairment caused by osteochondromas is almost non-existent. We will present the case of a young man, who had a complete non-traumatic subscapularis tear, where the tendon had been peeled off the lesser tuberosity by an osteochondroma. Diagnostic features such as MRI and arthroscopy are emphasized. The patient was successfully treated by open resection of the tumor and reattachment of the tendon with suture anchors.