Consolidation of democracy is one common problem found in majority of Southeast Asian countries. Lack of stable democratic institutions often leads a country to hybrid regime or some form of authoritarianism, such as military dictatorship or one-party rule. Myanmar and Thailand, the two immediate neighbours, are two such examples of weak democratic institutions where the role of military has been dominant in politics. Since its independence from Great Britain in 1948, there have been two military coups in Myanmar: 1962 and 1988. The military has played an important role in politics by successfully ruling the country for over four decades until the general election in 2010, which formally ended direct military rule. Despite the democratic transition and political reforms since 2011, the military continues to play a significant role in the country’s politics. Whereas in Thailand, there have been as many as 12 successful coups since the removal of absolute monarchy in 1932, with the latest coup in 2014. The article discusses the militarization of politics by examining the role of military in Myanmar, particularly under the National League for Democracy (NLD)-led civilian government which assumed power in 2016, and the entrenchment of military role in politics in Thailand, especially since the 2014 military coup. The article attempts to understand the conditions under which military intervenes and then holds on to power.