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Legislative leaders tend to be ideologically more extreme than their median members. Why? This paper shows that party members select extreme leaders as a strategic measure to anchor negotiations. Anchoring succeeds because the opposition understands that such leaders will not compromise on moderate legislation. Hence, rank-and-file members balance their own ideologies, and their assessments of political feasibility and institutional conditions, to select leaders who will pull agreements towards the ideal point of their median party member. Congressional voting data since 1900 confirms this account. When parties have selected extreme leaders, passed legislation aligns more closely with the preferences of the median caucus member. Party members also acknowledge the benefits of extreme leaders, referring to them more positively in newsletters sent to constituents. Such extremeness has the consequence, however, that less legislation gets passed. Additional comparative statics align with an account where institutional conditions can constrain the extremeness of leaders selected.