Why have labor movements in Mozambique, Zambia, and South Africa increasingly been marginalized from the economic debates that are taking place in their countries, even though they have supported ruling parties? Policy reforms such as trade liberalization, privatization, and revisions to labor legislation in all three countries partially account for the loss of power by organized labor as many scholars have claimed. Yet, these policy “adjustments” have also interacted with long-run, structural changes in production, distribution, and trade of goods as well as with processes of democratization to undermine the position of trade unions across much of southern Africa. The article explores this puzzle by first examining the different historical trajectories of organized labor in Mozambique, Zambia, and South Africa. It then analyzes how policy reforms, global restructuring, and democracy had similar consequences across all three cases; collectively, they produced declines in trade-union membership and weakened the influence of organized labor. Although trade unions face a number of daunting challenges, the conclusion traces emerging opportunities for labor to recover from its current malaise.