This study examines how nonprofit organizations are adapting their operations and missions amid systemic funding shifts under the Trump administration, with a focus on education-related programs. Drawing on Lester Salamon’s dual-imperative framework—which posits a tension between nonprofits’ survival imperative (adapting to market-driven funding landscapes) and their distinctiveness imperative (maintaining mission fidelity) —this research explores how nonprofit leaders navigate these competing pressures. Through interviews with Chicago-based intermediary 501(c)(3) nonprofits, this study identifies three critical strategies that enable these organizations to balance and uphold both imperatives: (1) active legal and mission risk management via diversified funding streams, (2) a nuanced understanding of local political philanthropic contexts, and (3) the forging of strategic alliances within the nonprofit sector. Ultimately these findings contribute to existing literature by arguing that intermediaries, when equipped with strategic agility, appropriate state-level support, and strong partnerships, have the potential to serve as pivotal actors and exemplars within the contemporary nonprofit ecosystem.