Navigating the fraught terrain of aging leadership, this chapter examines the complex relationship between a leader’s advanced age and the rise of public scandal. Drawing on both historical and contemporary cases, it explores how aging can become a strategic focal point for character attacks, often linked to broader controversies. The chapter considers the dual image of aging in political leadership—on one hand, a symbol of wisdom and seasoned judgment; on the other, a perceived liability marked by decline and inefficiency. Particular attention is paid to the role of public perception and media framing in constructing these narratives, illuminating the fine line between legitimate scrutiny and ageist bias.