A rich chiton assemblage consisting of more than 15,000 valves (shell plates) was collected by George P. Kanakoff (1897–1973) from Pliocene exposures of the San Diego Formation just north of the U.S./Mexican border. The assemblage includes 16 extant species, three extinct species (Callistochiton sphaerae n. sp., Lepidozona kanakoffi n. sp., and Amicula solivaga n. sp.), and three indeterminate species. The collection is dominated by the genus Callistochiton and also includes the genera Leptochiton, Oldroydia, Lepidozona, Stenoplax, Amicula, Mopalia, Placiphorella, Tonicella, Dendrochiton, and Nuttallina. This assemblage expands the known stratigraphic and paleogeographic ranges of many chiton genera and species and provides information about an apparent late Cenozoic diversification of chitons along the Pacific Coast of North America. Chitons appear to have diversified in the northeastern Pacific from the middle Miocene to Pleistocene, driven in part by regional increases in productivity and environmental heterogeneity during that time. The chitons are interpreted to have been deposited at inner-neritic depths (,25 m) in the mouth of a bay or in a continental shelf environment, and the annual temperature range and seasonality are inferred to have been similar to those that occur off the nearby San Diego coast today. However, the fossil assemblages also include a mixture of taxa that today range only to the north or to the south. The large sample sizes of chiton valves allow rigorous analysis of the ratio of valve types, revealing a divergence from the expected pattern. This divergence is even greater on average than what occurs in assemblages of chiton valves in Holocene sediments, revealing that taphonomic factors bias valve ratios long after valves are disarticulated. New foraminiferan and molluscan data indicate a middle or late Pliocene age of deposition for these beds, between 3.3 to 2.5 million years ago (Ma), and possibly about 3.0 Ma.