In the second half of the eighteenth century, Dutch bankers channeled investors’ funds to sugar and coffee plantations in the Caribbean, Surinam in particular. Agency problems between plantation owners, bankers, and investors led to an arrangement called negotiaties. Bankers oversaw plantations’ cash flows and placed mortgage debt with investors. We demonstrate how this securitization arrangement worked using market-wide data and detailed records from banker F. W. Hudig. During the boom, debt contracts and their securitization were an effective solution for planters, bankers, and investors. However, the market crashed after an oversupply of credit. This led to inefficient restructuring due to debt overhang.