Plants are amazing survival artists capable of enduring harsh environments and thriving in newly opened niches. My research seeks to broadly understand how environmental changes and biological interactions re-model the genealogical histories across the plant’s genome, with the aim of identifying key innovations responsible for adaptive changes. At the macroevolutionary scale, I will demonstrate how whole genome duplications buffered plants through a historical global warming, and how ancient gene flows created hyperdiverse clades in the neotropics and Chinese Hengduan Mountains. At the more recent evolutionary scale, I will focus on a radical form of biological interaction — parasitism. Integrating comparative genomics, physiology, computer vision, and collection-based sciences, I will illuminate a dynamic history of extinct host–parasite associations revealed by horizontal gene transfer and explore the functional implications of these alien genetic materials.