We investigate the insurance-motives of polluting firms’ charitable giving by analyzing donations from philanthropic foundations to nonprofit organizations in the local community. Our empirical setting exploits the National Ambient Air Quality Standards as localized exogenous shocks to pollution. Using regression discontinuity, we find that firms with more pollution subsequently donate more to local nonprofits. Firms maximize the insurance value of donations by reallocating donations to areas where they pollute the most. Potential mechanisms include firms’ local media coverage, reputational risk exposure, and history of regulatory noncompliance. Welfare analysis indicates that firms underpay for the insurance value of corporate philanthropy at the cost of society. Overall, the evidence suggests that firms leverage their reputation in local communities through corporate philanthropy as a form of insurance.