Understanding how some introduced plants achieve invasive status while most simply become naturalized is a fundamental question in invasion ecology. Traditional approaches comparing native and introduced plants have linked ruderal traits such as annual life history, high fecundity, and rapid growth rates to invasiveness. However, they do not explain why other introduced species bearing similar traits fail to become invasive, possibly because generic comparisons ignore local processes that drive community assembly. Herein, we contrasted native and introduced annuals in the context of local successional processes to elucidate how introduced annual bromes like cheatgrass (Bromus tectorum) overtake perennial grasslands in the intermountain western United States. We created disturbed plots and seeded them first with annuals representing natives, naturalized species, or invasive bromes. We then seeded plots with native perennial community dominants to examine how the different annuals influenced succession. Native annuals established transient populations that facilitated perennial establishment compared to unseeded controls, enabling the shift to perennial dominance. Naturalized annuals mirrored the natives, but invasive annuals maintained robust populations at high biomass that inhibited perennial establishment and impeded succession. Mechanistically, invasive annuals reduced soil moisture and elevated plant biomass, litter, and soil N. However, only litter abundance correlated with perennial seedling recruitment across treatments. Overall, litter showed a unimodal relationship wherein lower litter abundance associated with native and naturalized annuals appeared to facilitate perennial seedling establishment while higher litter levels generated by invasives appeared to suppress perennial establishment and inhibit succession. Additional experiments provided little support for the roles of pathogen spill-over or plant-soil feedbacks favoring the introduced bromes. The domination of perennial grasslands by annual bromes may be driven by litter buildup that allows these introduced plants to break local succession rules by acting as both early seral and climax species. Traits like litter accumulation may strongly influence invasion outcomes but are indistinguishable using trait comparisons lacking community context.