The Midwestern “Corn-Belt” in the United States is the most productive agricultural region on the planet despite being predominantly rainfed. In this region, global climate change is driving precipitation patterns toward wetter springs and drier mid- to late-summers, a trend that is likely to intensify in the future. The lack of precipitation can lead to crop water limitations that ultimately impact growth and yields. Young plants exposed to water stress will often invest more resources into their root systems, possibly priming the crop for any subsequent mid- or late-season drought. The trend toward wetter springs, however, suggests that opportunities for crop priming may lessen in the future. Here, we test the hypothesis that early season dry conditions lead to drought priming in field-grown crops and this response will protect crops against growth and yield losses from late-season droughts. This hypothesis was tested for the two major Midwestern crop, maize and soybean, using high-resolution daily weather data, satellite-derived phenological metrics, field yield data, and ecosystem-scale model (Agricultural Production System Simulator) simulations. The results from this study showed that priming mitigated yield losses from a late season drought of up to 4.0% and 7.0% for maize and soybean compared with unprimed crops experiencing a late season drought. These results suggest that if the trend toward wet springs with drier summers continues, the relative impact of droughts on crop productivity is likely to worsen. Alternatively, identifying opportunities to breed or genetically modify pre-primed crop species may provide improved resilience to future climate change. © 2021 The Authors. Food and Energy Security published by John Wiley & Sons Ltd.