The debate over union security arrangements is often presented as involving irreconcilable goals and values. Supporters of union security typically stress their importance to the union’s organizational strength and workers’ welfare. Right-to-work supporters, who favor banning such arrangements, typically emphasize employee freedom and choice. Our approach involves a unique comparison of both perspectives, which shows that neither perspective is completely compatible with safeguarding freedom. We therefore advocate reconciliation based on compulsory worker representation, which preserves the best freedom-enhancing properties of each perspective.