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The wealth gap between U.S. politicians and their constituents is well documented, but business owners and executives who seek and win elected office have received less scholarly attention. From the graft and corruption of the machine era to the formation of trade associations, government affairs units, and political action committees (PACs), business interests have a long history of involvement in American politics. Business takes a multi-pronged approach to political activities, not only lobbying policymakers but also supporting candidates and mobilizing employees. Over time and across places, large shares of candidates and elected officials at all levels of government have business backgrounds. Where—or under what conditions—are business candidates likely to run and win? With an original dataset that includes gender, race, occupational background, and political experience for nearly 4,000 mayoral candidates from 260 cities over 60 years, I investigate whether and how the electoral fortunes of business executive candidates vary systematically with characteristics of cities, such as geographic region, political institutions, and population.