The implementation of cycling infrastructure has been argued as a means to increase the overall mode share of cycling in communities. However, the implementation of such infrastructure has been fraught with political contentiousness across North America. In this paper, we interview ten municipal planners and engineers in the Greater Toronto and Hamilton Area, in order to determine how they implement cycling infrastructure in the face of political opposition. We find that there are four principal strategies used to secure the political support and ensure the construction of cycling infrastructure across the region: 1) piggybacking on public works projects, 2) using external grants and funding, 3) pre-emptively re-routing bicycling infrastructure, and 4) using a political champion. Through these strategies, we theorize that the politicization of cycling infrastructure is a result of the dominance of automobility in mobility, and that this politicization may lead to incomplete and less-than ideal cycling networks.