The sustainable management of polydiene waste represents a formidable challenge in the realm of polymer chemistry, given the extensive industrial utilization of polydienes due to their superior elastomeric properties. This comprehensive Perspective addresses the multifaceted obstacles hindering efficient recycling of polydienes, encompassing environmental concerns, technical limitations, and economic disincentives. We systematically dissect the influence of polydienes' chemical structures on their recyclability, tracing the evolution of polydiene utilization and disposal practices while assessing the current landscape of waste management strategies. Our investigation reveals the primary technical challenges associated with polydiene recycling, notably the energy-intensive nature of modification processes and the environmental detriments of prevailing disposal techniques. Furthermore, we critically evaluate existing recycling methodologies─including mechanical recycling, energy recovery, and chemical recycling─highlighting their respective merits, constraints, and environmental implications. Pioneering advancements in recycling technology, such as topochemical polymerization and computational prediction models, are spotlighted for their potential to revolutionize polydiene recycling. Looking forward, we delineate an optimistic trajectory for polydiene waste management, advocating for innovative polymerization methods, the exploration of milder recycling conditions, and the adoption of interdisciplinary approaches to bolster recycling efficiency. The Perspective culminates in a discussion on the pivotal role of policy frameworks, life cycle assessments, and economic analyses in shaping the future of polydiene recycling. Through this scholarly examination, we aim to catalyze further research and development efforts aimed at mitigating the environmental impact of polydiene waste, thereby contributing to the broader objective of sustainable chemistry.