Maritime piracy remains a persistent and geographically shifting threat to international shipping, generating direct losses (ransom payments, cargo theft, vessel damage) as well as substantial indirect costs related to delays, rerouting, insurance premiums, and private security measures. Despite a decline in high-profile incidents in some regions, the economic exposure of global supply chains to piracy risk remains significant, particularly along strategic chokepoints and in emerging high-risk zones. This study examines how piracy risk is identified, quantified, and incorporated into maritime risk portfolios by shipowners, insurers, and logistics operators. The paper develops an integrated economic framework for pricing maritime security under uncertainty. First, piracy risk is modeled using frequency–severity approaches commonly applied in actuarial science, incorporating spatial concentration, seasonal variation, and clustering effects. Second, cost components associated with preventive and reactive measures—armed guards, vessel hardening, convoy participation, rerouting, and kidnap and ransom (K&R) insurance—are analyzed as portfolio hedging instruments. Third, the study evaluates how piracy risk premiums are transferred along the value chain, affecting freight rates, charter agreements, and trade competitiveness. Using scenario analysis and sensitivity testing, the research compares optimal security investment strategies under varying attack probabilities and loss distributions. Results indicate that maritime security expenditures function as a hybrid financial–operational hedge, reducing tail risk while influencing overall portfolio volatility. Furthermore, diversification across routes and contract structures can mitigate concentrated exposure to piracy-prone areas. The findings contribute to financial risk management by positioning piracy not merely as a security issue but as a measurable economic variable that reshapes cost allocation and asset valuation in maritime transport. The study provides decision-support insights for insurers, shipowners, and policymakers seeking to balance security investments with capital efficiency in an evolving global risk environment.