The captain of a merchant ship has a unique leadership role based on his or her responsibility for the safety of the ship and cargoes, navigation, the security and welfare of the crew and passengers, the need to comply with the latest maritime regulations, and the objective of maximizing the shipowner’s profits. The level of accountability is high, as the captain’s discretion can override all prevalent rules and regulations to save the ship and crew, and the responsibility is 24/7. The captain must balance the interests of several stakeholders: not only the shipowner, crew and passengers, but the charterer, the shipper, the consignee, port authorities, and local and international administrative bodies. Issues faced by the captain include not only possible financial and reputational loss, but exposure to unethical practices, emergency situations like fire, explosion, foundering, injury, safety, and dealing with security threats, such as maritime piracy. Hope of rescue of ships being attacked can be far away; before help can arrive from outside, the captain has to protect the ship, crew and passengers, without arms and ammunition. The captain’s job includes preventing such external threats, but this can create dilemmas in balancing stakeholders’ interests, such as the need for constantly reducing costs.