The behaviour of appellate courts has long fascinated scholars. Specifically, scholars have been attentive to the effect of the political context on judicial outcomes. This paper focuses on the decision-making of the Philippine Supreme Court (“Court”) over multiple decades with particular attention to the influence of changes in the executive branch on the outcomes of cases brought to the Court. The analysis evaluates the decisions of the Court from 1970 through 2000, encompassing the turmoil of the Marcos years through the first few years of the tumultuous tenure of Joseph Estrada. We test the hypothesis, grounded in Galanter’s seminal work, that the government has substantial advantages in the legal system and thus enjoys greater success than other litigants. The government has theoretically unlimited resources with which to litigate, control over the staffing of the bench, and authority over, or at least major influence on, the laws that the courts interpret. As a result, the government is expected to win the majority of the challenges that come before the Court. The Philippines provides an excellent laboratory to test this thesis. In the Marcos era the Court faced a dictator professing “constitutional authoritarianism” whose regime ultimately was toppled by the People Power Revolution. His successor, Corazon Aquino, was initially embraced as the popular wife of an assassinated hero, Senator Benigno Aquino, Jr., but later faced a series of attempts to topple her regime. President Fidel Ramos served for 6 years leading the nation through a period of economic growth. Elected by a wide margin in 1998, President Joseph Estrada quickly lost the confidence of the Filipino people as well as the business and military sectors. By 2001, he was removed from office through political actions which some consider the People Power II. This analysis evaluates the winners and losers before the Philippine Supreme Court across the tenures of these presidencies with particular focus on the ability of the Filipino government to succeed when compared to individuals and businesses and the success of different regimes over time as the executive’s popularity surges and wanes. The results suggest, that like other institutions, the Philippine Supreme Court responded to the rise and fall of the personal politics that dominates the distribution of power in this Asian archipelago.