The ecological contexts that promote larger brains have received considerable attention, but those that result in smaller-than-expected brains have been largely overlooked. Here, we use a global sample of 2062 species to provide evidence that metabolic and life history tradeoffs govern the evolution of brain size in birds and play an important role in defining the ecological strategies capable of persisting in Earth's most thermally variable and unpredictable habitats. While some birds cope with extreme winter conditions by investing in large brains (e.g., greater capacity for planning, innovation, and behavioral flexibility), others have small brains and invest instead in traits that allow them to withstand or recover from potentially deadly events. Specifically, these species are restricted to large body sizes, diets consisting of difficult-to-digest but readily available foods, and high reproductive output. Overall, our findings highlight the importance of considering strategic tradeoffs when investigating potential drivers of brain size evolution.