30 years after the revival of local autonomy in South Korea, some consider Korean local autonomy has entered its age of “adolescence.” Moreover, the recently revised Local Autonomy Act emphasizes the expansion of local autonomy and increased decentralization. However, critics still point out that local elections are heavily influenced by national politics and previous studies on the reelection of chief elected officials of local governments have focused narrowly on national political factors, such as whether the party of the local government leader and the presidential party are the same and regionalism. In other words, most studies have assumed that local politics are beholden to national politics and have given less attention to local political factors and how they influence local elections. In this article, we analyzed candidate factors (including personal traits and fiscal variables) and party factors affecting the reelection of local government leaders (chief elected officials) in the 2014 and 2018 local elections. We included variables related to local politics, such as the presence of a dominant party in the region and fiscal expenditures that could increase the political influence of the local government leader. Our logistical regression results show differences between successful reelection factors in 2014 and 2018 elections, but party factor variables were the strongest predictors of local leader reelection in both years. In 2014, party affiliation and alignment between the political party of the local government leader and the presidential party predicted reelection success, while in 2018, alignment between the political party of the local government leader and the majority of local council predicted reelection success. Among candidate factors, age (+) predicted reelection success in both years, while education level (+) was only significant in 2018.