As GenAI and Agentic workflows transition from research benchmarks to core infrastructure in many traditional industries, the mandate for Trustworthy AI has shifted from a conceptual ideal to a rigorous engineering requirement. However, traditional enterprise deployment often treats trustworthiness as a checklist of independent constraints—fairness, privacy, robustness, explainability, and so on—rather than a coupled system. In this talk, we bridge the gap between algorithmic research and high-stakes deployment by examining the inherent trade-offs between aspects of trust. We demonstrate how common technical solutions meant to improve trust in one aspect often undermine trust in others. This presents a major roadblock to operationalizing algorithmic solutions in practice. Finally, we propose directions that researchers can follow to resolve these concerns, and guidance that practitioners can use today to manage these issues while facing strict regulatory and operational constraints.