In 1970s New York, landlords and major real estate associations argued that New York could stem the exodus of middle-income residents by creating greater opportunities for homeownership in a city that had long been dominated overwhelmingly by renters. They proposed converting middle-income rental housing into cooperatives, a process that would also enable former landlords to profit handsomely. Tenants, however, widely rejected apartment ownership, preferring the security of rent-regulated housing. This article traces the ensuing struggles between tenants, the real estate industry, and city officials over the nature of moderate- and middle-income housing in New York. The eventual success of the real estate industry enabled cooperative conversions to expand dramatically in the 1980s, but only by bargaining with tenants and activists, offering tenants noneviction plans, and discounting prices. This process helped to transform the city by underwriting a momentous turnaround in the real estate market, while signaling a larger embrace of market deregulation.