Shortly after the Cuban Revolution of 1959, the government eradicated Havana's most famous shantytown, Las Yaguas. This essay traces more than a decade of negotiations between shantytown networks and government officials that preceded the eradication. While previous scholarship has made virtually no mention of pre-1959 policies, many aspects of post-1959 slum clearance grew directly from earlier initiatives. These policies were shaped by two overlapping types of disputes: those about property, and those about poverty. Over time, officials sought to neutralize activism around property and local autonomy, focusing on social welfare and rehabilitation instead. Shantytown leaders used this compromise to maximize claims for social assistance after 1959. Yet the relocations also reaffirmed long-standing stigmas against the urban poor, labeling them as passive or noncompliant. In the end, Las Yaguas residents were defined as beneficiaries, not heroes, of the Cuban Revolution.