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A rising tide of research on distributional conflict has shown that strong climate policy becomes more feasible when it creates economic winners, not just losers. For instance, labor unions are more likely to support energy transitions when they expect to gain jobs for their members. However, merely offering the prospect of benefits may not be enough to persuade interest groups to join the coalitions needed for policy enactment. If winners do not trust that they will receive their intended benefits from a policy, they are unlikely to make substantial contributions to collective efforts to secure the policy’s adoption. Yet there is relatively little work on how policies can be designed to increase winners’ certainty that they will benefit. In this paper, we examine six policymaking episodes across three states, focusing on whether organized labor was effectively incorporated into climate policymaking. We trace the path of carbon pricing from early failure to recent success in Washington and how coal miners in West Virginia came to support a version of the Clean Air Act amendments in 1990 and Build Back Better three decades later. We show how failure to provide certainty can frustrate efforts to build coalitions around stringent policy proposals even in favorable political environments such as low-carbon economies, and how successfully providing certainty can secure allies even under unfavorable conditions. The findings offer important lessons for scholars, policymakers, and campaigners: creating winners without creating certainty is politically inefficient.