Freiberg's disease is a rare disorder affecting the distal metatarsal bones. With no quantitative estimate of its prevalence, the exact pathophysiology of Freiberg's disease is not clearly recognized. However, micro-trauma, repetitive injury, and vascular insufficiency have been implicated the most as predisposing factors for the condition. Freiberg's disease typically presents in adolescent females with higher body mass index (BMI), involving the second and third metatarsal bones with an eventually destructive inflammatory process comprising swelling, hotness, tenderness, and marked restriction of movement. We report a greatly unique and highly atypical presentation of Freiberg's disease in a middle-aged African male with bilateral and symmetrical involvement of the first metatarsal bones, a pattern of involvement that is considered highly anecdotal and atypical rarity of presentation of Freiberg's disease.