This study develops a new measure of longevity expectations and, using a structural approach, explores the effect of these expectations on the retirement behavior of the older Americans. The new measure elicited from self-reported survival probabilities in the HRS reveals that white Americans born in the 1940s and 50s have shorter anticipated life expectancy than their counterparts born in the 1930s and, moreover, the longevity gap is bigger for low educated groups. This finding contrasts with the standard cohort life tables estimates of the Social Security Administration (SSA) which predicts an upward trend in life expectancy over time. Through simulations, I show that the birth cohorts of 1940s and 50s may potentially retire earlier than what is expected by the SSA. These findings may imply that the Social Security System is less redistributive than it might appear because low-educated individuals obtain their benefits for significantly fewer years than more educated individuals, especially in later birth cohorts.