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Which politicians are most likely to benefit from collusion with organized crime? Works to date focus on how criminal group members can benefit by electing their own or their longstanding sympathizers. I provide a new theory of candidate-criminal collusion that explains how previously overlooked candidates leverage their dissimilarities with organized crime to strike deals and minimize the subsequent physical, legal, and political risks of association. Specifically, dissimilar candidates leverage their differences 1) as a veiled threat of retaliation should their criminal partner renege and 2) to increase their legal cover when subverting the law. Using fine-grained administrative data on voting in criminally-dominated territory, an original survey with local candidates in Brazil, and a large corpus of text data from voter complaints to the state electoral authority, I provide evidence for both of these mechanisms and demonstrate that candidates most likely to strike electoral deals with criminal organizations – and gain votes in criminally-governed territory – often have little in common with the criminal group or electorate in these areas. These findings bring together the literatures on representation and crime in politics by demonstrating which types of candidates are likely to reap electoral returns to colluding with criminal groups.