What can the history of computer chess teach us about the future of geospatial development? As AI fundamentally alters how we develop GIS software, write spatial algorithms, process imagery, and automate workflows, our community is currently struggling with existential and practical questions that the chess world has been navigating for decades. By looking at how chess players adapted to, survived, and ultimately thrived alongside super-intelligent machines, this session discusses options for FOSS4G professionals looking to navigate the new rules of the GIS game in the age of AI.