We are at a pivotal time in human history, as the agricultural sector undergoes consolidation coupled with increasing energy costs in the context of declining resource availability. Although organic systems are often thought of as more sustainable than conventional operations, the lack of concise and widely accepted means to measure sustainability makes coming to an agreement on this issue quite challenging. However, an accurate assessment of sustainability can be reached by dissecting the scientific underpinnings of opposing production practices and crop output between cropping systems. The purpose of this review is to provide an in-depth and comprehensive evaluation of modern global production practices and economics of organic cropping systems, as well as assess the sustainability of organic production practices through the clarification of information and analysis of recent research. Additionally, this review addresses areas where improvements can be made to help meet the needs of future organic producers, including organic-focused breeding programs and necessity of coming to a unified global stance on plant breeding technologies. By identifying management strategies that utilize practices with long-term environmental and resource efficiencies, a concerted global effort could guide the adoption of organic agriculture as a sustainable food production system.