Managing production environments in ways that promote weed community diversity may enhance both crop production and the development of a more sustainable agriculture. This study analyzed data of productivity of maize (corn) and soybean in plots in the Main Cropping System Experiment (MCSE) at the W. K. Kellogg Biological Station Long-Term Ecological Research (KBS-LTER) in Michigan, USA, from 1996 to 2011. We used models derived from population ecology to explore how weed diversity, temperature, and precipitation interact with crop yields. Using three types of models that considered internal and external (climate and weeds) factors, with additive or non-linear variants, we found that changes in weed diversity were associated with changes in rates of crop yield increase over time for both maize and soybeans. The intrinsic capacity for soybean yield increase in response to the environment was greater under more diverse weed communities. Soybean production risks were greatest in the least weed diverse systems, in which each weed species lost was associated with progressively greater crop yield losses. Managing for weed community diversity, while suppressing dominant, highly competitive weeds, may be a helpful strategy for supporting long term increases in soybean productivity. In maize, there was a negative and non-additive response of yields to the interaction between weed diversity and minimum air temperatures. When cold temperatures constrained potential maize productivity through limited resources, negative interactions with weed diversity became more pronounced. We suggest that: (1) maize was less competitive in cold years allowing higher weed diversity and the dominance of some weed species; or (2) that cold years resulted in increased weed richness and prevalence of competitive weeds, thus reducing crop yields. Therefore, we propose to control dominant weed species especially in the years of low yield and extreme minimum temperatures to improve maize yields. Results of our study indicate that through the proactive management of weed diversity, it may be possible to promote both high productivity of crops and environmental sustainability