Democracy denied: lessons from incarcerated communities and US territorial residents

It’s hard to convey the power of witnessing two groups, often hidden and made invisible, be seen and centered. In 2025, I was facilitating a cycle of New Profit’s Unlocked Futures program, a cohort-based portfolio investing in transforming the US criminal legal system, where we convene and provide strategic support for organizations led by formerly incarcerated and directly impacted leaders. That year, we chose to hold our final convening as a cohort in Puerto Rico—a choice years in the making, as I had been reflecting on the similarities between the experiences of the US territories and those impacted by the US carceral system. Witnessing these similarities play out in real time would prove transformative to me, the participants, and how we might conceptualize what it means to work toward a more democratic United States.

Funding for impact

We began our closing convening, as we always begin, with a commitment to grounding in place. During this trip to Puerto Rico, as we celebrated the conclusion of Unlocked Futures 4, we spent the afternoon with three powerful local leaders, Issel Masses, Executive Director, Sembrando Sentido; Mari Mari, Executive Director, Kilometro Cero; and Dr. Edna Benitez Laborde, director of university studies program for incarcerated people at the University of Puerto Rico; in dialogue about their work and systems change. What emerged was a journey through familial and communal histories, US colonialism and carcerality, and the struggles for self-determination. Cohort participants made connections to their own experiences as formerly incarcerated US citizens. They shared experiences of being denied their right to vote in state and federal elections, being excluded from or having limited access to federal social safety nets such as SNAP, Medicaid, or affordable housing, and the state imposing on their agency and autonomy.

I wonder if, as funders, we might examine more closely a central contradiction within our “democracy”: that millions of US citizens are systemically denied full democratic participation and access to opportunity.

For Fred Ward, Director of Building Freedom Ohio, these conditions reflect the long legacy of slavery in the United States.

“The 13th Amendment was abolished with conditions that allowed the directly impacted in America to inherit yet another form of enslavement,” said Ward, who is an alum of New Profit’s Unlocked Futures 4 cohort.

“Democracy is not only about who gets to vote. It is also about who gets to decide how public resources are generated, allocated, and spent, and whether those decisions respond to people’s needs,” said Issel Masses, Executive Director of Sembrando Sentido. “Puerto Rico, one of five US colonies, exposes the limits of democratic participation when fundamental decisions about our collective future remain outside the control of the people they affect.”

As we took stock of America’s 250th this summer, and look ahead to a pivotal election cycle, the distance between the founding promise of democracy and who can fully participate in it today is brought into even sharper focus. I wonder if, as funders, we might examine more closely a central contradiction within our “democracy”:  that millions of people living in the US are systemically denied full democratic participation and access to opportunity.

The decisions we make as funders, from where we convene grantees to who gets chosen for investment, can either further entrench those inequities or disrupt them. If we desire a world where all US citizens can fully exercise their agency, then as a social impact sector, we must commit to uncovering what has been intentionally hidden. As Dr. Edna Benitez Laborde said during our panel in Puerto Rico, “[Prisons] hide people, but you don’t solve problems.” It is in the hidden communities and invisible experiences that we will find solutions to our problems as a society.

Two nations, one made invisible 

As a partner at New Profit leading the Unlocked Futures program, I bring my experience as a community organizer, culture worker, and movement capacity builder to this work, and a 15-plus-year career spanning youth work, government, and nonprofit management and consulting. In 2022, as I prepared to launch my first investment cycle for Unlocked Futures, I noticed something in our organization’s language defining eligibility: “Organization operates in and primarily serves communities in the United States.”

What did we mean by the United States? We weren’t explicit about naming US territories and therefore were missing an opportunity to do a few things:

• See the whole: When we aren’t explicit about the system or space we’re targeting, we flatten what is often a dynamic, nuanced, and complex set of experiences. We end up with default thinking or what’s most dominant, not the full picture.
• Elevate the systems experts: Being hidden means having intimate knowledge and experience with how these systems work. The analysis of the issue, vision for change, and how we’ll change it must be grounded in that expertise.
• Create lasting impact: To invest in truly impactful and sustained economic, environmental, and social change, we must center the insight of leaders and organizations most impacted by systems of oppression. As funders, we can help uncover hidden experiences and turn toward a world that centers the dignity of all people.

Dr. King spoke of “The Other America”—the idea that while the United States speaks of “one nation, indivisible,” social inequality creates two different nations. One “overflowing with the milk of prosperity and the honey of opportunity,” and the other “that constantly transforms the buoyancy of hope into the fatigue of despair.” Of the two, the second America is too often made invisible. If we want to address the conditions that lead to that inequality, we must first labor to make them visible in all our funding considerations.

When it was time to announce the call to submit an application for Unlocked Futures, we decided to specify that we were seeking to fund social entrepreneurs in the United States and its territories. This decision provided a chance to clarify internally that if we want to fund the solutions and organizations most proximate to the experiences of the United States, we must include the communities most invisible to us.

This shift also allowed us to uncover powerful commonalities between the experiences of those in the territories and those who have been or are incarcerated in the United States.

[The two groups] share the experiences of second-class citizen status, of facing barriers (including the literal barriers of borders and prisons) that define you as “other,” and of being made invisible in policy, narratives, and even mental models.

That same year, I met Issel Masses, a former New Profit grantee who I had the opportunity to build with and advise while she was in our portfolio. Catalyze (New Profit’s investment vehicle for early- to mid-stage organizations) portfolio organizations are paired with a strategic advisor to connect with throughout the year. In addition to the cohort team, they serve as a trusted advisor to the CEO or ED. This is an extension of our “all in” stance and understanding that funding alone is not enough to sustain and grow organizations doing critical work. Many of my conversations with Masses focused on the critical decisions, urgent needs, and opportunities she was navigating as the founder and executive director of Sembrando Sentido, a Puerto Rico-based nonprofit building civic infrastructure to help communities understand and shape decisions about public resources and hold institutions accountable. Through that advising space, I deepened my understanding of how communities shaped by very different histories can encounter intersecting structures of political exclusion, institutional neglect, and constrained decision-making power.

Issel’s invitation for us to convene the next Unlocked Futures cohort in Puerto Rico offered the opportunity to connect these two experiences and a chance to keep dollars flowing to people at the intersections. Being together in person revealed not only the deep similarities, but a searing glimpse into the true nature of American democracy today, as exposed by two groups denied full participation in it.

Both communities experience domination, punishment, and exclusion from institutions and processes that claim to uphold democratic values. They share the experiences of second-class citizen status, of facing barriers (including the literal barriers of borders and prisons) that define you as “other,” and of being made invisible in policy, narratives, and even mental models. This shows up in the following ways:

Lack of political empowerment

This is the autonomy to represent your own interests within a political context, or more simply, the practical ability to speak for and about themselves within the political system that governs their lives—and for that to meaningfully and systemically have weight. This is particularly important for groups that are on the margins, disadvantaged, or invisible. Our World in Data provides a useful framework for understanding political empowerment, organized across three dimensions: fundamental civil liberties, civil society participation, and descriptive representation. Ultimately, when people across diverse populations can express political agency, societies benefit from greater government accountability, more effective public spending, and economic and technological progress.

Democracy in practice, domination, and punishment

The experiences of Puerto Rico and the US mainland show the overlapping dynamics of a larger exclusionary system. Puerto Rico has one of the most progressive voting laws for those in prison—under Puerto Rican law, incarcerated individuals never lose their right to vote regardless of the severity or classification of their offense. Additionally, the Puerto Rico State Commission on Elections establishes physical polling stations inside every correctional facility. In the United States, 48 out of 50 states bar individuals with felony convictions from voting while incarcerated or post-release, and formerly incarcerated communities face a dizzying array of state laws that govern the restoration of voting rights.

While incarcerated people in Puerto Rico can vote for local legislators and the governor, the island’s status as a territory does not allow them to vote for US president or elect voting members of Congress. On the US mainland, incarcerated people cannot vote. Yet, their presence bolsters census counts for the congressional districts where prisons are built, inflating the federal representative weight of the district while denying incarcerated folks democratic agency.

Under conditions that restrict their democratic rights and political participation, incarcerated and formerly incarcerated communities face significant institutional barriers to holding public way to hold public officials accountable for neglect of their safety, healthcare, labor conditions, and economic opportunity.

Directly impacted individuals across both of these geographies experience incomplete versions of democracy. Those on the US mainland are explicitly excluded from civic participation—their bodies are counted to shape state power, but they are silenced and their voices are legally erased through a carceral system with deep roots in racial exclusion and disenfranchisement. For incarcerated communities in Puerto Rico and the island as a whole, structural colonial exclusion limits their collective political voice and agency to effect change.

Uncovering what is hidden

Puerto Rico’s history is one of continuous colonization, from Spanish rule to US territorial status. As a US territory, residents of Puerto Rico enjoy no political representation—merely a single non-voting member in Congress and no vote for president. Puerto Rico is subject to unequal federal funding arrangements for essential services, including Medicaid funding and a nutritional assistance program that provides lower benefits than SNAP. At the same time, federal authority can override local policy choices. For example, although Puerto Rico’s Constitution expressly prohibits the death penalty, federal prosecutors can still seek capital punishment for eligible federal crimes committed on the archipelago. These contradictions illustrate how colonial governance limits Puerto Rico’s ability to determine policies affecting its own people.

Meanwhile, incarcerated and formerly incarcerated Americans face similar barriers to participation in their own democracy. Twenty-three states have banned voting for the incarcerated, while 15 extend that ban to anyone on probation or parole, and 10 have long-term or permanent voting bans for anyone who has been incarcerated. That’s not even counting the immense logistical barriers to voting, both during incarceration and long after, including the difficulty of getting an ID.

Rather than having meaningful opportunities to shape the decisions affecting their lives, these communities are subjected to state systems of surveillance, control, and punishment. They are stripped of their rights, denied protections under the Constitution, pushed into unpaid or underpaid labor, and face inhumane conditions and slow or limited response to the crises they face, whether COVID-19 or natural disasters. 

Solving the issues these groups face means solving for larger problems that keep the United States from functioning as a true democracy. If we solve for how disaster relief gets implemented and immediately accessed for the territories, we solve for how the entire country accesses these urgent resources. If we solve for the experience of formerly incarcerated people having access to IDs and getting their right to vote, we’re actually solving voting disenfranchisement for everybody. As Black queer feminist frameworks have long argued, when we tend to those most impacted by our systems, it serves everybody. To quote the Combahee River Collective Statement, “If Black women were free, it would mean that everyone else would have to be free, since our freedom would necessitate the destruction of all the systems of oppression.”

“Communities in Puerto Rico have a deep understanding of the challenges they face, the changes they want to see, and the solutions needed to improve their lives. Yet, the institutions and systems that shape our collective future have historically excluded our voices, disregarded our expertise, and constrained our ability to influence decisions that affect us,” said Masses. “Advancing democracy requires making these structures of exclusion impossible to ignore and transforming the institutions and practices that sustain them. Our partnership with New Profit has shown how philanthropy can engage in difficult conversations, challenge its own assumptions, and rethink its practices to help dismantle barriers to meaningful democratic participation.”

If we want true democracy to endure—or begin—in the next 250 years, we should reflect on those who are a part of our democracy and yet blocked from participation. We should be asking: What was hidden in order for 250 years of democracy to be celebrated while places like Puerto Rico lack full autonomy, sovereignty, and the same access to rights and equitable treatment that states have? How can 250 years of democracy be celebrated while attacks on the Voting Rights Act persist? What and who is hidden to tell this story?

We, funders committed to transformation, must be willing to confront the structures and institutional practices that have historically rendered communities invisible and excluded them from democratic participation. We must listen to, elevate, and invest in the voices and movements that have long challenged these systems of exclusion, and ask ourselves what must change within our own institutions to support their efforts. What would it mean, for example, to ensure that all incarcerated and formerly incarcerated people can exercise their voting rights, both in law and in practice?