Alewife (Alosa pseudoharengus) are the preferred prey species of the top piscivore predators in the Lake Ontario food web and are an essential constituent in the bioaccumulation of persistent organic contaminants. Year-class samples collected in 2016 represent the alewife age ranges of 2015 (Age-01) sequentially dating back to 2008 (Age-08). The most abundant contaminant measured in Lake Ontario alewife (151.5 ng/g) were total polychlorinated biphenyls (PCBs), increasing at a rate of 11.8 ng/g per year on an age-averaged concentration basis. Total mercury demonstrated the largest percent increase (240%) accumulated over alewife ages of 1–8 years. Average total concentrations of the most abundant polychlorinated dibenzo-p-dioxin isomer (2378-tetrachlorinated dibenzo-p-dioxin (TCDD), 1.3 pg/g) and polychlorinated dibenzofuran isomer (2378-tetrachlorinated dibenzofuran (2378-TCDF), 6.6 pg/g) comprised most of the overall total dioxin (2.5 pg/g) and total furan concentrations (8.7 pg/g). The vast majority (69%) of alewife total toxic equivalence (TEQ) was comprised of the non-ortho coplanar PCBs. Both mammal and avian wildlife protection values based on total TEQ were uniformly exceeded for the dioxin-like compounds measured in Lake Ontario alewife. Ontogenetic dietary influences expressed a significant impact on Age-01 alewife age-contaminant relationships and age-stable isotope concentrations and trends for legacy contaminants. Total Hg and all dioxin-like contaminants did not demonstrate the Age-01 ontogenetic dietary effects found in legacy contaminants. A prominent polychlorinated naphthalene (PCN) concentration peak measured in year-class Age-04 alewife was followed by a corresponding lake trout peak 3–4 years later illustrating a unique example of trophic-level contaminant uptake and concomitant integration delay.