Few institutions have done more to improve working conditions for the middle class than labor unions. Their efforts, of course, cost money. To fund union activities, thousands of collective bargaining agreements across the nation have long included provisions permitting employers to require employees to pay “fair share” or “agency” fees. In public unions—when the employer is the government—this arrangement creates tension between two important values: the First Amendment’s protection against compelled expression and the collective benefits of worker representation. When confronted with this tension forty years ago in Abood v. Detroit Board of Education, the Supreme Court struck an uneasy compromise, allowing public sector unions to recoup expenses for collective bargaining but not for political activity. For decades, the decision has been a lightning rod with some scholars calling for its reversal and others insisting on its preservation. In the meantime, the realities of modern public sector collective bargaining have changed, and First Amendment jurisprudence has evolved. The Supreme Court, which recently granted certiorari in Janus v. AFSCME, now has the opportunity to reconsider Abood’s fragile compromise. This Article offers a new way forward within the First Amendment that honors the importance of both union activity and free expression. It proposes a method to reconcile these twin interests while also updating the doctrine to account for state legislative efforts, modern union realities, and First Amendment jurisprudential developments. The Article argues that agency fees should be brought into step with current political contribution and campaign finance jurisprudence. Under this middle-ground approach, some agency fees, but only those that are “closely drawn” to avoid unnecessary expressive infringement, will remain lawful. This approach may not satisfy those who ardently oppose agency fees of any kind or those who want Abood’s rule fully upheld. Still, it emerges as the best way forward through a difficult terrain: It avoids the false dichotomy between union and political activities, respects state legislatures that craft innovative collective bargaining statutes, and grounds public sector agency fees with other coherent aspects of First Amendment jurisprudence.