Previous research has documented a strong relationship between currently living in the redlined zones of the 1930s and suffering from a higher prevalence of disease. However, little is known about the relationship between historical redlining, modern-day redlining, and current resident health outcomes. This paper aimed to simultaneously model the associations between both historical redlining and modern-day redlining on current health outcomes. In this paper, we used structural equation modeling to uncover relationships between current and historical redlining practices and modern-day life expectancy, exploring two levels of potential mediating factors: (1) racial segregation and structural racism; and (2) mediating health outcomes. We analyzed data from 11,661 census tracts throughout the United States using historical redlining data from 1940, modern redlining data from 2010 to 2017, racial segregation and structural racism indices from 2010 to 2019, health outcome data from 2021 to 2022, and life expectancy data from 2010 to 2015. Historical redlining was measured using Home Owners' Loan Corporation (HOLC) ratings, which ranged from 1.0 for favorable neighborhoods ("greenlined") to 4.0 for unfavorable ("redlined") neighborhoods. Modern-day redlining was measured using Home Mortgage Disclosure Act (HMDA) data, which were transformed into four quartiles, ranging from level 1 (low mortgage rejection rates) to level 4 (high mortgage rejection rates). We found a significant relationship between historic redlining and current life expectancy, with average life expectancy decreasing steadily from 80.7 years in HOLC 1 tracts to 75.7 years in HOLC 4 tracts, a differential of 5.0 years between the greenlined and redlined tracts. We also found a significant relationship between modern-day redlining and current life expectancy, with average life expectancy decreasing steadily from 79.9 years in HMDA 1 tracts to 73.5 years in HMDA 4 tracts, a differential of 6.4 years. In the structural equation model, historical redlining had a total effect of decreasing life expectancy by 1.18 years for each increase of one in the HOLC rating. Modern-day redlining had a total effect of decreasing life expectancy by 1.89 years for each increase of one in the HMDA quartile. This paper provides new evidence that the legacy of redlining is not relegated to the history books but rather is a present and pressing public health issue today.