Broader structural developments in Japan in the past two decades—decline of clientelist practices, partisan de-alignment, and decentralization—have dissolved traditionally close ties between national and local party systems, creating an environment conducive to the emergence of local parties. In this context, popular chief executives in four regions launched new parties. I trace how these parties emerged and how national parties reacted to them, from the appearance of the new-party leaders to the 2011 local elections. In comparing the four cases, two factors appear to shape their trajectories: the urbanness of their electoral environments and the responses of the two national parties at the local and the national level. In dealing with the new challengers, both the Liberal Democratic Party and Democratic Party of Japan experienced considerable intraparty conflict and defections, indicating a process of delinking between national and local party systems.