A successful transaction of digital contents is primar-ily dependent on security policies, trust relationships and benefit equilibriums among various participants in a DRM (Digital Rights Management)-enabling contents value chain ecosystem. We first analyzed basic value chain architectures in existence, together with some fundamen-tal security and trust requirements. And then, a state-of-the-art anatomy of the security and trust related to DRM was presented from different stakeholder' perspectives. Next, some challenges for multi-party mutual trust, not just inclined to any of participants, were proposed based on the holistic consideration of the digital contents/rights protection and the benefits balance. Finally, a conclusion was drawn that the rights-benefits-centric DRM ecosys-tem and the resulting trust relationship are crucial for the survivability of the contents industry.