The intricate nature of ship stability has resulted in a slow and discontinuous evolution of the subject and its measurement in Naval Architecture despite two millennia having lapsed since its initial conception and measurement. This has been influenced by two major factors; Naval Architects of the past were primarily “men of practice” and hence not able to dwell in the scientific concepts bounding and defining Naval Architecture whilst the scientists occasionally being involved with ship stability and safety may not necessarily understand how ships are designed and operated. This modus operandi has had profound effects on how damage stability measurement and flooding risk assessment have evolved. This paper provides a critical historical account of such developments from antiquity to present.