Drawing on historical and rational choice institutionalism, this article seeks to explain the evolution of the Workers' Party as it moved from opposition to government between 1989 and 2002. The Partido dos Trabalhadores (PT), a once radical and programmatic party, came to look more like its catchall competitors over time. This shift resulted from the heightened emphasis placed on immediate vote maximization after Brazil's adoption of market reforms rendered the party's socialist project unviable. Vote maximization made the PT more susceptible to the institutional incentives for building electoral and political support in Brazil, incentives that induce parties to weaken their programmatic positions, forge opportunistic alliances, and resort to patronage and even corruption. To grow, the PT ended up applying such tactics, which it had long condemned. Yet its adaptation was incomplete and uneven due to historical legacies that hindered change. The analysis thus suggests that institutions evolve in response to changing environmental conditions but in ways constrained by past trajectories.