Nila Kartika Wati
The intersection of the United States criminal legal system and the political status of U.S. territories has emerged as a focal point for philanthropic organizations seeking to address what they describe as a "central contradiction" in American democracy. Through programs like New Profit’s Unlocked Futures, venture philanthropy is shifting its focus toward leaders with lived experience in these systems, aiming to dismantle the structures that render millions of citizens "invisible" to the federal government and the broader public. This movement reached a significant milestone in 2025 during a cohort convening in Puerto Rico, where social entrepreneurs and civil rights advocates identified profound parallels between the colonial status of U.S. territories and the disenfranchisement of the formerly incarcerated.
The Evolution of Venture Philanthropy and the Unlocked Futures Initiative
Unlocked Futures was established as a cohort-based portfolio by New Profit, a venture philanthropy firm dedicated to backing social entrepreneurs who are driving systemic change. The program specifically targets organizations led by formerly incarcerated individuals and those directly impacted by the criminal legal system. Since its inception, the initiative has sought to provide not only financial capital but also strategic support to help these leaders scale their impact on the U.S. carceral landscape.
A pivotal shift in the program’s strategy occurred in 2022, when leadership began re-evaluating the definition of "the United States" within their eligibility criteria. Historically, many philanthropic organizations have focused their domestic efforts exclusively on the 50 states and the District of Columbia, often overlooking the nearly 3.6 million Americans living in U.S. territories. By explicitly expanding their scope to include Puerto Rico, Guam, the U.S. Virgin Islands, American Samoa, and the Northern Mariana Islands, New Profit aimed to address a demographic that experiences many of the same systemic exclusions as the carceral population.
In 2025, this strategic expansion culminated in a final convening of the Unlocked Futures 4 cohort in Puerto Rico. The gathering served as a platform for dialogue between U.S. mainland leaders and local advocates, including Issel Masses of Sembrando Sentido, Mari Mari of Kilometro Cero, and Dr. Edna Benitez Laborde of the University of Puerto Rico. The discussions focused on the historical and contemporary parallels between colonial governance and carceral control.
Comparative Disenfranchisement: The Status of the "Other America"
The 2025 convening highlighted a shared reality of "second-class citizenship" among residents of U.S. territories and justice-impacted individuals. This concept, often referred to as "The Other America"—a term popularized by Dr. Martin Luther King Jr.—describes a segment of the population that is systemically denied the "milk of prosperity and the honey of opportunity" afforded to the rest of the nation.
Data from the Sentencing Project and other civil rights monitors indicate that approximately 4.6 million Americans are disenfranchised due to a felony conviction. While 48 states bar individuals from voting while incarcerated, the laws governing post-release voting rights vary wildly across the country, creating a confusing patchwork of eligibility that often results in "de facto" disenfranchisement even after sentences are served.
Conversely, Puerto Rico presents a unique paradox. Under local law, incarcerated individuals retain the right to vote in island-wide elections, and the Puerto Rico State Commission on Elections maintains polling stations within correctional facilities. However, despite this progressive local stance, no resident of Puerto Rico—regardless of their criminal record—can vote for the President of the United States, nor do they have voting representation in Congress. This lack of federal agency mirrors the experience of incarcerated individuals on the mainland, whose bodies are counted for census purposes to bolster the political weight of the districts where prisons are located, yet who are legally barred from participating in the democratic process.
Structural Barriers to Economic and Social Welfare
The similarities between these two groups extend beyond the ballot box into the realm of federal social safety nets. Participants in the Unlocked Futures cohort noted that formerly incarcerated individuals often face significant hurdles when attempting to access the Supplemental Nutrition Assistance Program (SNAP), Medicaid, and affordable housing due to "collateral consequences" of their convictions.
Puerto Rico and other territories face analogous restrictions at the institutional level. Residents of Puerto Rico are excluded from the federal SNAP program and instead receive the Nutritional Assistance Program (NAP), which typically offers lower benefit levels and less flexibility. Furthermore, federal Medicaid funding for territories is capped, unlike the open-ended funding provided to states, leading to chronic underfunding of healthcare systems.
Legal experts point to the "Insular Cases" of the early 20th century as the foundation for this disparate treatment. These Supreme Court decisions established that certain U.S. territories are "unincorporated," meaning the Constitution does not fully apply to them. This legal framework allows Congress to treat territories differently than states, a dynamic that local leaders argue limits their ability to respond to crises such as natural disasters or economic downturns.
Direct Testimony: The Legacy of the 13th Amendment and Colonialism
During the 2025 convening, Fred Ward, Director of Building Freedom Ohio and an Unlocked Futures alum, argued that the current conditions facing justice-impacted people are a continuation of the 13th Amendment’s "punishment clause," which abolished slavery "except as a punishment for crime." Ward suggested that this constitutional loophole allowed for the creation of a permanent underclass that inherits "yet another form of enslavement" through the carceral system.
Issel Masses, Executive Director of Sembrando Sentido, expanded this critique to the territorial context. "Democracy is not only about who gets to vote," Masses stated. "It is also about who gets to decide how public resources are generated, allocated, and spent." She noted that Puerto Rico’s status as a colony exposes the limits of democracy when fundamental decisions about a community’s future are made by federal authorities who are not accountable to the local population.
Dr. Edna Benitez Laborde, who directs university studies for incarcerated people in Puerto Rico, emphasized that both prisons and colonial structures serve to "hide people" rather than solve the underlying social problems. The consensus among the advocates was that the invisibility of these populations is a deliberate feature of the current system, designed to maintain the status quo by excluding those most affected by policy failures from the decision-making process.
The Strategic Role of Philanthropy in Systems Change
The Unlocked Futures program represents a shift in philanthropic methodology, moving toward what New Profit calls an "all in" stance. This approach involves pairing organization leaders with strategic advisors who provide ongoing mentorship and capacity building. For Issel Masses and Sembrando Sentido, this partnership has been instrumental in building the civic infrastructure necessary to hold Puerto Rican institutions accountable and to help communities understand the allocation of public resources.
The decision to convene in Puerto Rico was also a deliberate attempt to redirect philanthropic capital toward the archipelago. By bringing mainland donors and leaders to the island, the program sought to bridge the gap between "invisible" communities and the resources they need to thrive. The goal is to move beyond traditional charity and toward "transformative investment" that addresses the root causes of inequality.
Analysis of Implications for the Future of American Democracy
As the United States approaches its 250th anniversary, the findings from the Unlocked Futures 2025 convening suggest that the health of American democracy may be measured by its treatment of those at the margins. Advocates argue that solving the problems faced by the most impacted populations—such as ensuring voting rights for the formerly incarcerated or achieving political sovereignty for territories—will inherently strengthen the democratic system for all citizens.
This perspective aligns with the "Combahee River Collective" framework, which posits that the liberation of the most oppressed groups necessitates the destruction of all systems of oppression. In a modern context, this means that addressing the logistical barriers to voting for a formerly incarcerated person in Ohio or ensuring equitable disaster relief for a resident of San Juan are not isolated issues, but are central to the integrity of the national democratic experiment.
The broader impact of this work is expected to influence how other philanthropic organizations define their geographic and demographic priorities. If the social impact sector continues to commit to uncovering "what has been intentionally hidden," it may lead to a more inclusive and representative version of American governance.
Conclusion and Future Outlook
The 2025 Unlocked Futures convening in Puerto Rico has set a new precedent for how philanthropy can engage with the complexities of U.S. citizenship and political agency. By highlighting the overlapping dynamics of carcerality and colonialism, the program has challenged the narrative of a "one nation, indivisible" and instead pointed toward the work required to bridge the divide between the two Americas.
Moving forward, the challenge for both funders and policymakers will be to translate these insights into legislative and systemic change. This includes ongoing efforts to restore voting rights, equalize federal funding for territories, and dismantle the collateral consequences of incarceration. As the dialogue continues, the voices of those who have been most excluded are likely to become the primary architects of a more robust and equitable democratic future.
