On May 15, 2024, at the Istana, Singapore’s fourth prime minister Lawrence Wong took his oath of office and was officially sworn in, taking over from prime minister Lee Hsien Loong. This political transition is significant for a host of different reasons, and so, across two episodes, we take a deeper dive with Dr. Kenneth Paul Tan of Hong Kong Baptist University. We look back, and we look ahead. We look back, across Singapore’s first three prime ministers or three generations of leadership. We then look ahead to three potential electoral scenarios for Mr. Wong and his ruling People’s Action Party or PAP.