With the phase-out and regulation of some flame retardant chemicals, the production and usage of organophosphate triester flame retardants (OPFRs) has increased in recent years. In the present study, 14 OPFRs (either chlorinated, brominated or non-halogenated) were analyzed in egg pools of 10-13 individual herring gull eggs from five colonial nesting sites for 11 years spanning 1990–2010, (for a total of n=55 egg pools) in the Laurentian Great Lakes of North America (Chantry Island, Fighting Island, Agawa Rocks, Toronto Harbour and Gull Island). OPFR profiles varied slightly between colony sites and collection years. For all five sites tris(2-chloroisopropyl) phosphate (TCIPP), tris(2-chloroethyl) phosphate (TCEP) and tris(2-butoxyethyl) phosphate (TBOEP) were detected, while triphenyl phosphate (TPHP) was only quantifiable in eggs from Chantry Island and Gull Island collected in 2008 and 2010. For the 2010 egg pools, the ΣOPFR concentrations were generally low and ranged from 2.02 to 6.69 ng/g wet weight (ww). ΣOPFR concentrations in 2010 were significantly higher (p<0.05) than they were between 1990 and 2004 (4.06 vs. 1.55 ng/g ww, respectively). In a pilot examination of Great Lakes aquatic food webs, 2010-collected alewife and rainbow smelt (major herring gull fish prey) and lake trout from western Lake Erie and Ontario, only contained TBOEP at low to sub ng/g ww concentrations. These results demonstrate that low to sub-ppb concentrations of at least three OPFRs, TCIPP, TCEP and TBOEP, have been persistent in herring gull eggs from the Great Lakes for at least the past 20 years, probably bioaccumulate mainly via the fish diet, and are transferred to the eggs of exposed herring gulls.