The compositional scope of polymer zwitterions has grown significantly in recent years and now offers designer synthetic materials that are broadly applicable across numerous areas, including supracolloidal structures, electronic materials interfaces, and macromolecular therapeutics. Among recent developments in polymer zwitterion syntheses are those that allow insertion of reactive functionality directly into the zwitterionic moiety, yielding new monomer and polymer structures that hold potential for maximizing the impact of zwitterions on the macromolecular materials chemistry field. This dissertation describes the preparation of zwitterionic choline phosphate (CP) methacrylates containing either aromatic or aliphatic thiols embedded directly into the zwitterion. The polymerization of these functional CP methacrylates by reversible addition-fragmentation chain-transfer (RAFT) methodology yields polymeric zwitterionic thiols (PZTs) containing protected thiol functionality in the zwitterionic units. After polymerization, the protected thiols are liberated to yield thiol-rich polymer zwitterions which serve as precursors to subsequent reactions that produce polymer networks as well as polymer-protein bioconjugates through reversible disulfide formation or by permanent addition mechanisms. Moreover, the aromatic PZTs are found to stabilize oil-in-water interfaces when evaluated by pendant drop tensiometry. Overall, PZTs represent a novel and versatile materials platform to access a variety of properties and chemistries with wide ranging potential applications in the macromolecular field, from stimuli-responsive surfactants to polymer-protein therapeutics.