There is significant uncertainty as to what types of remedial affirmative action programs in government contracting are constitutional. This uncertainty adversely affects policymakers, courts, government agencies, and businesses. This Note discusses how one remedial contracting affirmative action effort, the Department of Transportation (DOT) Disadvantaged Business Enterprise (DBE) Program, has a unique cooperative federalist structure that can help policymakers address this constitutional uncertainty. This structure, constrained constitutional experimentation, has three aspects: (1) an underlying context of constitutional uncertainty, (2) the use of the federal government’s Spending Power to create incentives for and constrain state action, and (3) the preservation of state governments’ flexibility to experiment. Because of this structure’s ability to transfer the results of experimentation from one state to others, the DBE program helps policymakers resolve the constitutional uncertainty surrounding remedial contracting affirmative action programs.