For the past decade, circular economy (CE) has gained widespread recognition as an umbrella of strategies that can help society better manage resources in the pursuit of sustainability. A CE favors Circular Business Models (CBMs) that cycle existing materials, extend the life of products, intensify the use of fewer resources, or dematerialize the economy. However, whilst many businesses and supply chains have tried to become more circular in recent years, not all have been successful. The limited application of circularity potentially indicates the existence of trade-offs at the business or supply chain levels; however, there is limited empirical evidence to draw upon to theorize about such tensions and trade-offs, particularly evidence from units of analysis broader than single focal companies. This study therefore aimed to address this knowledge gap by investigating the positive and negative implications of cycling, extending, intensifying, and dematerializing business models for the business and for the supply chain. The phenomenon was explored through eight qualitative case studies in different industries. Data were collected from semi-structured interviews and triangulated with secondary publicly available sources. As a result, we present our findings on the positive and negative implications of CBMs, contributing to the theory with propositions on the trade-offs of the CE. This study also has implications for practitioners by helping them understand and contrast different circular possibilities in their businesses and supply chains.