The research employs descriptive research methods to investigate the supply and demand dynamics of structured settlement markets, wherein individuals enter into contractual agreements to settle a personal injury case through the delivery of an annuity issued by a highly rated insurance carrier. This dissertation examines the characteristics of structured settlement markets, their similarities to other markets, and investor behavior under different macroeconomic conditions. The dissertation draws on data from public sources, market indexes, and existing literature on similar topics from other asset classes (Commercial Mortgage-backed Securities (CMBS) & High Yield Bonds). The data analysis will take a top-down approach using quantitative research methods. The motivation for this research study is to enhance visibility into the structured settlement market relevant to practitioners and influence future research on structured settlements and similar investments. / Business Administration/Risk Management and Insurance