This research explores the effectiveness of Tax Increment Financing (TIF) as a financial tool to stimulate residential and commercial development in downtown Winnipeg. Cost is a commonly cited barrier to developing downtown, resulting in deteriorating and vacant city centers. TIF can remove some of the financial barriers to development, ultimately revitalizing downtown and benefitting the community as a whole. A comprehensive literature review was used to inform unstructured interviews with urban planners, developers, and various city officials to determine how TIF could be effectively implemented to revitalize Winnipeg’s downtown. Examining precedents from Winnipeg and across North America highlight the positive and negative impacts of TIF, as well as its promotion as a tool for urban renewal. TIF is an effective method of increasing property values, and encouraging development in priority areas. Tailoring present TIF methods to local conditions can help avoid increasing property taxes, wrongful use of land expropriation, or insufficient revenue generation.