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Studies on incumbency are dominated by Western scholar studies by employing quantitative approach to see incumbency trend at congressman and senator elections. The gap of that academic research so far has given wider opportunity for incumbency studies in Indonesia as a new democratic country with a very complex electoral process. By conducting field research and partly ethnographic approach, this paper explains selected local elections cases which are relevant to incumbency literature and analysis. The results of this study indicated that incumbency candidates are facing both opportunities structure and disadvantages caused by embedded factors that are candidate profile, bureaucracy power, capital access, and provided information, and also the dynamic external factors which consist of: protest voters, political parties, corruption issues, etc. This also became an alternative answer to why many incumbent candidates were defeated in concurrent elections in 2015 and 2017.