“We have to change the Constitution,” announced President Rodrigo Duterte in July 2019, “whether federal or whatnot.” Beginning in late 2014, when he first began projecting himself on the national stage, the strongman from Davao City has frequently proclaimed—albeit with inconsistent levels of emphasis—the virtues of the Philippines moving from a unitary to a federal system. Since starting his six-year term in 2016, President Duterte has put revision of the 1987 constitution back on the country’s political agenda. But to what end and in what way? Alongside the multiple versions of federalism proposed by various groups (both official and ad hoc), there has been increasing attention to the virtues of electoral system redesign. This avenue of reform not only presents lower risks of unintended consequences but also has substantial potential to address two longstanding ills of Philippine democracy: weak and incoherent political parties and deeply entrenched patterns of patronage. Particular focus is on a highly dysfunctional party list system, a markedly non-proportional system used to elect 20% of the House (declared “evil” by Duterte for straying far from the original goal of promoting representation of “marginalized sectors”). Other targets of reform include a multi-member plurality system that guarantees high levels of intra-party competition (and is used to elect 80% of the country’s 18,000 electoral posts). This paper examines the meandering path to political reform in Duterte’s Philippines, and opportunities that may arise—amid the twists and turns—for a major revamp of the country’s current electoral system.