Leonardo da Vinci set out to produce a true treatise of anatomy, since in his time no such work existed. His drawing of the spine is a formidable example of his genius. Since artworks by Leonardo are appreciated for their accuracy and careful adherence to the subject represented, we examined Leonardo’s spine as one would a radiograph, looking for evidence of osteoporotic fractures or signs of osteoarthritis. The dorsal and lumbar vertebrae show a slightly wedge-shaped deformity without “radiological” signs of fracture. Instead, signs of osteoarthritis can be noted at the lumbar vertebrae. With his extraordinary eye for detail, Leonardo produced an image that foreshadows those that radiology would later make available to clinicians for the diagnosis of problems linked to vertebral degeneration.