Hypotheses regarding the evolution of many clades are often generated in the absence of data from the fossil record and potential biases introduced by exclusion of paleontological data are frequently ignored. With regard to body size evolution, extinct taxa are frequently excluded because of the lack of body mass estimates—making identification of reliable clade specific body mass estimators crucial to evaluating trends on paleontological timescales. Herein, I identify optimal osteological dimensions for estimating body mass in extinct species of Pan-Alcidae (Aves, Charadriiformes) and utilize newly generated estimates of body mass to demonstrate that the combination of neontological and paleontological data produces results that conflict with hypotheses generated when extant species data are analyzed in isolation. The wing-propelled diving Pan-Alcidae are an ideal candidate for comparing estimates of body mass evolution based only on extant taxa with estimates generated including fossils because extinct species diversity (≥31 species) exceeds extant diversity, includes examples from every extant genera, and because phylogenetic hypotheses of pan-alcid relationships are not restricted to the 23 extant species. Phylogenetically contextualized estimation of body mass values for extinct pan-alcids facilitated evaluation of broad scale trends in the evolution of pan-alcid body mass and generated new data bearing on the maximum body mass threshold for aerial flight in wing-propelled divers. The range of body mass in Pan-Alcidae is found to exceed that of all other clades of Charadriiformes (shorebirds and allies) and intraclade body mass variability is recognized as a recurring theme in the evolution of the clade. Finally, comparisons of pan-alcid body mass range with penguins and the extinct †Plotopteridae elucidate potentially shared constraints among phylogenetically disparate yet ecologically similar clades of wing-propelled divers.