Christopher Alexander was often characterized—and sometimes seemed to characterize himself—as “sui generis,” a radical and perhaps even eccentric thinker on architecture, technology, culture, and nature. That perception in turn has led many to dismiss Alexander’s work as too idiosyncratic to be operationalized in the pragmatic world of planning and building. Here we show, however, that Alexander’s core ideas have strong parallels in contemporary network science, mathematics, physics, and philosophy, and in the pragmatic world of technological design (including computer software). We highlight a remaining gap in translating Alexander’s work into practical tools and strategies for implementation—a gap that is tantalizingly near to being bridged.