A massive, high-stakes political conflict has erupted over oil sands pipelines -- Keystone XL to the Gulf Coast, two pipeline proposals to the Pacific Coast, and new proposals for alternative routes to Eastern Canada. Alberta’s fossil fuel wealth is virtually landlocked, and as the growth of US demand for Canadian oil has stagnated, the sector’s profitability and future growth have been jeopardized. Environmentalists, recognizing the strategic importance of these pipelines to the growth of the sector, have aggressively sought to block their approval in an effort to limit the expansion of the oil sands. The conflict has spilled over into federal Canadian politics, interprovincial politics, and Canadian-American relations. This paper will examine this political controversy from a perspective that focuses on two core factors: the operation of institutional veto points and the distribution of risks and benefits across jurisdictions. The political risk to major infrastructure projects is a function of five factors: the number of institutional veto points; whether opposition groups have access to veto points; whether the project can take advantage of existing infrastructure; the salience of place-based, concentrated environmental risks; and the jurisdictional separation of risks and benefits We will see that each of the projects faces formidable political risks, but that these risks vary in type and magnitude by project. The key question is whether sufficient political pressure can be mounted to overcome these obstacles.