There have been several descriptions of variant anatomy of the long head of the biceps tendon (LHBT). A recent literature review identified 8 cases of anomalous intracapsular attachment of the LHBT. In this report, we discuss a distinctive case of a young athlete who presented with symptoms consistent with bilateral superior labrum anterior to posterior (SLAP) tears that were unresponsive to conservative measures. Magnetic resonance imaging and arthroscopic findings of this patient confirmed that the patient had type II SLAP tears, a Buford complex anteriorly, and perhaps most important, confluence of the biceps tendon itself to the undersurface of the capsule within the rotator interval. Our case proposes that anomalous insertion of the LHBT, as well as other labral and biceps anchor variations, are not always a benign finding at the time of arthroscopy. In this particular case, the tethering of the biceps tendon to the capsule is thought to have increased stress on the superior labrum and contributed to the development of the bilateral symptomatic type II SLAP tears that were identified and treated in this young athlete.