Making Cycles

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The Potential of Generational Philanthropy

Tomorrow is Giving Tuesday, a national movement dedicated to inspiring generosity, where individuals and organizations come together to support causes that create meaningful change in our communities. Generational philanthropy—where wealth and values are passed down across family lines—has never been more influential on determining where these funds come from. Baby Boomers are projected to transfer $84 trillion in assets to their heirs over the coming decades. Millennials and Gen Z, the recipients of this wealth, are also projected to bring more progressive values to the table, emphasizing transparency, social justice, and measurable impact. As the wealth is passed to these younger generations, our society will see a new opportunity to tackle the biggest issues faced by our society, including criminal justice reform.

In the past, justice-impacted communities have remained largely excluded from the benefits of generational wealth. Wealthy families, often untouched by the criminal justice system, usually lack the personal motivation and experiential context to invest in reform that helps justice-impacted communities. Though Baby Boomers are the most generous generation in American history, the majority of their donations go towards religious institutions, universities, and healthcare charities. Generational philanthropy has transformational potential, and redirecting this wealth into criminal justice reform could unlock a virtuous cycle that would reduce poverty, foster community stability, and end cycles of incarceration.

Why Post-Incarceration Employment is so Important

Imagine if even a fraction of generational wealth were channeled into initiatives that address criminal justice reform. This would require shifting from a charity-driven model, a favorite even for 84% of Millennials, to a model of giving focused on long-term, systemic investment. Philanthropic dollars could fund vital programs such as education within prisons, vocational training for justice-impacted people, and reentry support services. These programs are proven to reduce recidivism—research shows that even 30 days of post-incarceration employment can cut re-offense rates by over 50%. Studies also reveal that formerly incarcerated individuals working full time are 53% more likely to avoid re-incarceration than those working part-time or sporadically.

The reality is difficult to swallow – formerly incarcerated individuals are five times more likely than the general population to be unemployed, with only 37.9% securing jobs within the first four years of release. This systemic exclusion perpetuates poverty, recidivism, and suppresses overall economic growth. 

The Multiplier Effect of Decreasing Recidivism

When justice-impacted people can get jobs, a multiplier effect occurs in our society. Access to quality employment reduces reliance on public welfare systems and creates safer, more equitable communities. Individuals who receive comprehensive reentry support—including job training, housing assistance, and mental health services—are significantly more likely to reintegrate successfully and less likely to recidivate, cutting societal costs associated with repeated incarceration.

Programs like The Last Mile (TLM) are designed to reverse this trend. TLM equips justice-impacted individuals with in-demand skills, significantly improving their chances of securing meaningful employment upon release. The model is working—TLM alumni have a recidivism rate of less than 5%, a stark contrast to the 61% average recidivism rate in the U.S. within 10 years of release. A substantial portion of the individual donors supporting TLM are households and families contributing generational wealth, representing 83% of individual funding sources.

Generational wealth offers the unique opportunity to drive these systemic changes at scale, fostering shifts in opportunity, stability, and wealth-building in communities disproportionately affected by the criminal justice system. These investments would not only uplift individuals but also revitalize entire neighborhoods, fostering long-term economic resilience.

Foundations Leading the Way in Criminal Justice Reform

Some family foundations are already paving the way for generational wealth to drive criminal justice reform. The Kresge Foundation, established in 1924, has invested billions in equity and opportunity, including its Culture of Justice initiative. This program, launched in 2019, awarded $1.2 million to community-based organizations addressing systemic challenges in justice-impacted communities, particularly for boys and men of color. By amplifying authentic narratives and empowering affected individuals to lead reform efforts, Kresge demonstrated how targeted philanthropy can drive systemic change and foster resilience​.

Similarly, the Ted Slavin Family Foundation embodies the power of intergenerational giving. Founded by entrepreneur Ted Slavin, the foundation supports initiatives ranging from healthcare to housing, focusing on uplifting underserved communities. Through partnerships and strategic investments, the foundation exemplifies how family philanthropy can address systemic inequities. Foundations like Kresge and Slavin are becoming critical for ensuring that justice-impacted individuals gain the resources and opportunities needed to break cycles of poverty and incarceration​

Creating a Virtuous Cycle

Until now, generational philanthropy has largely overlooked criminal justice reform. Without cultural or financial backing, justice-impacted communities have been caught in a vicious cycle that bars them from stable wealth, perpetuating the cycles of poverty and incarceration. By reimagining the way we view generational wealth, a virtuous cycle can emerge. Here’s how:

The Generational Justice Loop:  a philanthropic approach that reframes giving as an investment in systemic change, rather than temporary relief, and breaks the vicious cycle of incarceration and wealth disparities.

1. By prioritizing funding for education, reentry programs, and job opportunities for justice-impacted individuals, generational philanthropy can fund initiatives that are proven to reduce recidivism and social spending while increasing wealth and stability in justice-impacted communities.
2. These programs prepare justice-impacted individuals for sustainable employment and contribute to breaking the cycle of incarceration. Further programs that assist justice-impacted individuals with housing, mental health services, and community support are critical to successful reintegration, and philanthropic investments in these areas not only reduce recidivism but also foster stability within families and communities. 
3. Justice-impacted individuals gain the resources they need to avoid re-incarceration, build wealth, and ultimately reinvest in their own communities.  This allows for economic independence to develop in neighborhoods disproportionately affected by the criminal justice system. 
4. With the accumulation of wealth and stability, those impacted by the justice system will have the largest incentive to facilitate further criminal justice reform. As more resources are invested into improving criminal justice practices, the virtuous cycle becomes self-sustaining. All it needs is the initial push to get the flywheel of the Generational Justice Loop turning.
   

Choose Your Cause Wisely

Generational philanthropy holds immense potential to address one of society’s most pressing challenges: the cycle of poverty and incarceration that prevents millions from enjoying wealth and stability. By prioritizing criminal justice reform, families can redefine wealth as a tool for systemic change, creating a legacy that aligns with values of equity and social responsibility.

As the Great Wealth Transfer unfolds, there is an urgent need to direct these resources toward building a fairer, more inclusive society. A model like the Generational Justice Loop offers a pathway to achieve this, fostering a virtuous cycle that benefits not only justice-impacted individuals but society as a whole. 

By Chris Redlitz, Cofounder at The Last Mile, with Robert Roche, Content Marketing Director at The Last Mile

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