This article explores the transformation of demolition and revitalization practices over the past two decades, using the 2008 redevelopment of the Military Aviation Plant No. 4 (WZL-4) in Warsaw, Poland, as a pivotal case study. At the time, the project stood out for its forward-thinking approaches to stakeholder governance, waste management, and infrastructural integration, setting benchmarks for post-industrial redevelopment in Central Europe. This paper analyzes the WZL-4 revitalization in the context of its era—highlighting practices that were considered innovative at the time and remain relevant today—while contrasting them with contemporary strategies employed up to 2025. Drawing upon a comparative methodology and current scientific literature, the study identifies trends, innovations, and persistent challenges in the field of demolition and brownfield regeneration. It highlights key technological, procedural, and managerial advancements including BIM-based project coordination, risk-informed planning, smart monitoring, and circular economy integration. The paper contributes a dual-perspective evaluation: both retrospective and forward-looking, offering insight into how best practices have evolved and providing a roadmap for future sustainable urban redevelopment projects grounded in systemic innovation.