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Lloyd's of London was a unique institution: an insurance market of competing syndicates in which syndicate managers simultaneously wrote insurance policies and acted as the fiduciary agents of outside investors who provided their underwriting capital. A market leader for 300 years, Lloyd's engendered innovation and expertise. Faced with declining market share in the 1980s and an influx of new investors, several syndicates have led to charges of fraud and incompetence. The case is useful for illustrating moral hazard, adverse selection, reputational and repeated game equilibriums. It is also useful for illustrating the advantages and disadvantages of market transaction in comparison to transactions within the firm.