This patient was diagnosed with a melanocytoma of the left eye. This condition, found commonly, is thought to be a benign condition, with 'far less than 1% of patients progressing to melanoma' as per a recent article by Shields and Shields of Wills Eye. This patient, however, proved to be one of those rare instances. Two years later this patient presented with enlargement of the melanocytoma. Referral to a regional retinal specialist led ultimately to the patient being sent to Wills where juxtapapillary choroidal malignant melanoma was confirmed. The patient underwent transpupillary thermotherapy, which eliminated the tumor but greatly reduced vision due to damage of the nerve layer. Over two years went by with the eye remaining tumor-free, but ischemia secondary to the thermotherapy led to subretinal neovascularization. The eye was treated aggressively with pan-retinal photocoagulation, but was eventually finally enucleated. This case shows the importance of careful observation and photo-documentation of even the most 'benign' pigmented lesions.