The recent actions of former Trinidad and Tobago Prime Minister and PNM leader, Dr. Keith Rowley, have sparked significant political discourse. On November 17, Dr. Rowley hosted a media conference at his Diego Martin residence under the banner of the ‘Office of the Former Prime Minister,’ a title that does not officially exist. This move has raised eyebrows and concerns about his intentions to institutionalize his post-retirement influence on public affairs. While Dr. Rowley, as a private citizen, retains the right to free expression, his frequent interventions and press conferences have created a sense of disarray within the PNM. Current Opposition Leader Pennelope Beckles appears increasingly sidelined as Dr. Rowley continues to dominate the political narrative. His prolific commentary, including numerous Facebook posts, contrasts sharply with Ms. Beckles’ more collaborative approach. This dynamic not only undermines her leadership but also weakens the PNM’s strategic coherence. The situation highlights a broader issue in democratic governance, where the presence of multiple figureheads can dilute a party’s message and effectiveness. Dr. Rowley’s persistent public presence, while legally permissible, raises questions about his political judgment and the legacy of his governance.