Since the introduction of the sphygmomanometer at the beginning to the 20th century, the significance of diastolic (DBP), Systolic (DBP) and pulse pressure (PP) as hypertensive cardiovascular risk factors has been controversial. These historical controversies are reviewed. Initially, DBP was thought to be the best measure of risk, but more recently both SBP and DBP, which ever is higher, are used in classifying hypertensive cardiovascular risk. There are problems with the present guidelines, in that SBP and DBP represent only two inflection points on the propagated pulse wave that is measured by cuff readings at the peripheral brachial artery. The heart is exposed to the central aortic pressure not to the brachial artery pressure. Moreover, both peripheral vascular resistance and large artery stiffness contribute to hypertensive cardiovascular risk. In middle-aged and elderly, elevated SBP is a better surrogate measurement of resistance than DBP, but SBP underestimates large artery stiffness. PP, the difference between peak SBP and end DBP, is the single best blood pressure surrogate for large artery stiffness. Epidemiological studies over the past decade point to SBP and DBP as the best cardiovascular risk markers for young subjects, whereas PP takes over as the more powerful risk marker for middle-aged and elderly subjects. These findings support the concept that cardiovascular events are more related to the pulsatile stress of large artery stiffness during systole than the steady-state stress of small vessel resistance during diastole. Therefore, at similar elevations of SBP, subjects with isolated systolic hypertension are at greater risk for cardiovascular events than those with combined systolic/diastolic hypertension.