Every product leader knows that unchecked legacy products and mounting technical debt act as a "hidden tax," draining engineering capacity and crippling innovation velocity. This panel tackles the political, organizational, and financial gravity of portfolio rationalization. We will discuss and debate the strategic frameworks required to set clear, data-driven sunset criteria for profitable but stagnant products. Attendees will gain actionable insights on how to quantify technical debt as a business risk, secure alignment with finance and engineering leaders, and effectively reallocate freed-up resources to fund the next generation of growth products and competitive AI initiatives.