Up until its defeat in the August 2020 parliamentary elections, the communist successor party in Montenegro, Democratic Party of Socialists (DPS), represen-ted the only uninterrupted ex-communist incumbency in Southeastern Europe. This chapter will process trace the political course, ideology and transformation of this party throughout the 30 years that it held the reins of power in the tiny Adriatic republic. In so doing, the chapter will also analyze the transformation of the Montenegrin party system from competitive authoritarianism and one-party dominant system to a more inclusive but fragile democracy recently. I will rely on fieldwork that I did in Montenegro in April 2019, during which I conducted se-mi-structured elite interviews with party leaders and deputy leaders (from Mon-tenegrin, Serbian, Bosniak and Albanian parties), current and former ministers, members of parliament and Montenegrin academics and public intellectuals. Besides this, I will also draw on secondary sources to properly contextualize my arguments.