The phasing of winter-to-summer precipitation anomalies in the North American monsoon (NAM) region 2 (113.25°W–107.75°W, 30°N–35.25°N—NAM2) of southwestern North America is analyzed in fully coupled simulations of the Last Millennium and compared to tree ring reconstructed winter and summer precipitation variability. The models simulate periods with in-phase seasonal precipitation anomalies, but the strength of this relationship is variable on multidecadal time scales, behavior that is also exhibited by the reconstructions. The models, however, are unable to simulate periods with consistently out-of-phase winter-to-summer precipitation anomalies as observed in the latter part of the instrumental interval. The periods with predominantly in-phase winter-to-summer precipitation anomalies in the models are significant against randomness, and while this result is suggestive of a potential for dual-season drought on interannual and longer time scales, models do not consistently exhibit the persistent dual-season drought seen in the dendroclimatic reconstructions. These collective findings indicate that model-derived drought risk assessments may underestimate the potential for dual-season drought in 21st century projections of hydroclimate in the American Southwest and parts of Mexico.