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In this study we examine two channels through which corporate political contributions could affect firm-level tax outcomes. First, firms that make political contributions are more likely to be singled out in rifle-shot tax legislation and receive firm-specific tax relief. The ex-ante payoff to political contributions if rifle-shot tax relief is the only benefit of making political contributions is negative, but for some firms the payoff is enormous, akin to playing a lottery. Second, firms also receive tax benefits when members of their industry cohort make political contributions, regardless of the firm’s own political contributions, consistent with politicians taking actions that benefit an entire class of assets or type of investment.