The field of nanotechnology and regenerative medicine has been progressing at a rapid pace. From theranostic nanoparticles to biomaterials, the possibilities seem endless. Researchers at the University College London have developed and patented a technology to manufacture a new breed of novel nanocomposite material called polyhedral oligomeric silsesquioxane poly(carbonate-urea) urethane (POSS-PCU). The enhanced biocompatibility, superior mechanical engineering properties, and augmented degradative resistance of POSS-PCU render it capable of functioning as a scaffold for bioartificial organs, nanoparticles for biomedical applications, and a coating for medical devices. Indeed, POSS-PCU has been used in 3 first-in-man studies as a bypass graft, lacrimal duct, and, most notably, the world's first synthetic trachea. Our group has a vested interest in the development of next-generation smart biomaterials that use nano-inspired technologies and mobilize the regenerative capacity of biological systems. Herein we provide a concise and authoritative account of the evolution of biomaterials research within a University College London and POSS-PCU context, with further emphasis on the prospects and challenges involved in driving the future of bioartificial organs in tandem with advanced drug delivery systems in the realm of nanotechnology and regenerative medicine.