Hybrid offspring of crops and their wild relatives commonly possess non-adaptive phenotypes and diminished fitness. Regularly, diminished success in early-generation hybrid populations is interpreted to suggest reduced biosafety risk regarding the unintended escape of novel traits from crop populations. Yet hybrid populations have been known to evolve to recover fitness relative to wild progenitors and can do so more rapidly than wild populations, although rates of evolution (for both hybrid populations and their wild progenitors) are sensitive to environmental context. In this research, we asked whether hybrid populations evolved more rapidly than wild populations in the context of soil moisture. We estimated evolutionary rates for 40 Raphanus populations that varied in their history of hybridization and environmental context (imposed by an experimental moisture cline) in two common gardens. After five generations of growing wild and crop-wild hybrid populations across a soil-moisture gradient, hybrid populations exhibited increased seedling emergence frequencies (~6% more), earlier emergence (~1 day), later flowering (~3 days), and larger body size (15–35%)—traits correlated with fitness—relative to wild populations. Hybrid populations, however, exhibited slower evolutionary rates than wild populations. Moreover, the rate of evolution in hybrid populations was consistent across evolutionary watering environments, but varied across watering environments in wild populations. These consistent evolutionary rates exhibited in hybrid populations suggests the evolution of robust traits that perform equally across soil moisture environments—a survival strategy characterized as “jack of all trades.” Although, diverse integrated weed management practices must be applied to wild and hybrid genotypes to diversify selection on these populations, evaluating the evolutionary rates of weeds in diverse environments will support the development of multi-faceted weed control strategies and effective integrated weed management policies.