Pectoralis major tendon ruptures are being reported with increasing frequency and primarily occur in young, high demand, male patients. The injury results from an eccentric contracture of the muscle most commonly while performing the bench press maneuver during weight training. In the setting of both acute and chronic injury, physical examination is critical for a timely and accurate diagnosis. During physical examination, comparison with the opposite side is imperative, and findings may include swelling, ecchymosis, loss of the anterior axillary fold, and a decreased pectoralis major index. Surgical treatment of acute ruptures is superior to nonsurgical treatment and results in improved functional outcomes and high levels of return to work and sport. Repair of chronic tears is more challenging and may require reconstruction with autograft or allograft tissue. Despite advances in surgical technique, tendon rerupture, persistent pain, and wound infection remain a concern.