The research examined the contrasting experiences of the Philippines and Indonesia, two countries with multiparty presidential systems, in managing executive-legislative relations. While the presidentialism framework warns of institutional gridlock, the analysis reveals that Rodrigo Duterte and Joko Widodo effectively navigated these dynamics through the strategic use of presidential powers. The qualitative comparative analysis examines how the respective leaders leveraged coalition-building, patronage, and budgetary powers in divergent ways by applying a presidential toolbox framework. Duterte heavily relied on porkbarrel allocations and patronage to secure legislative support in the Philippines, while Jokowi pursued broad coalition-building, integrating opposition parties into the Indonesian cabinet. The findings suggest that the successful application of presidential toolboxs, rather than institutional design alone, plays a critical role in ensuring political stability within fragmented party systems. This challenges deterministic assumptions about the perils of presidentialism, offering a more nuanced understanding of executive adaptability in Southeast Asia. The research contributes to the comparative literature by refining the coalitional presidentialism model in emerging democracies, illustrating how distinct leadership styles, institutional arrangements, and informal practices influence the viability of multiparty presidential systems.