The body naturally creates biomacromolecules to lubricant joints and provide incredibly low friction under tremendous load for decades. One of the biolubricants, lubricin, demonstrates boundary mode lubrication and chondroprotective abilities that arise from its composition and structure. As a promising therapeutic approach for the treatment of joint diseases such as osteoarthrosis (OA), the challenge to produce lubricin recombinantly restricts its clinical application, which inspires the design of synthetic molecules that mimic lubricin’s structure. In this dissertation, a class of lubricin mimetic diblock copolymers, consisting of a cationic cartilage binding block and a brush lubrication block, are synthesized and their tribological properties are evaluated in comparison to lubricin (Chapter 2). Like lubricin, the tribological properties of these polymers are dependent on the molecular architecture. The roles of structure are explored to characterize how changing the molecular architecture affects the lubrication on cartilage surfaces and the results are summarized as a set of design principles of synthetic lubricants (Chapter 3). Additionally, this class of polymers demonstrates their ability to bind to and lubricate bone surfaces, which is absent in natural lubricin, thus extending its potential application as a therapeutic approach for OA treatment (Chapter 4).