a protest in Tulsa calling for the release of inmates.

a protest in Tulsa calling for the release of inmates.

Last month, billionaire Twitter and Square CEO Jack Dorsey’s Start Small fund directed $10 million to criminal justice organization REFORM Alliance to help bolster COVID-19 relief efforts and deliver personal protective equipment to prison and jail facilities across America. As we reported, in early April, Dorsey announced he would use $1 billion of his shares in Square to fund pandemic relief efforts through a newly formed limited liability company (LLC) called Start Small. That $1 billion figure is dynamic, though, and the value of the stock has already increased.

Dorsey has stepped up with fast-moving philanthropy during these last few months, supporting a range of organizations in areas like hunger relief, education, and global health. According to a #startsmall tracker, the fund had disbursed a whopping $152 million over 100 grants between April 2 and June 18—with much of this giving flying under the radar. Dorsey’s priorities have also been evolving, as he said they would when he started the fund. And he’s teamed up at times with government, leading nonprofits and other funders. Last week, for example, the Start Small and Rihanna’s Clara Lionel foundations donated $1 million total to Policing Equity, supporting their national initiative leveraging data to improve policing outcomes in America.

Dorsey’s eight-figure donation to REFORM is among his biggest to date. The criminal justice organization will use the funds to purchase and deliver more than 10 million masks, along with other PPE, to prisons across all 50 states. The goal is to ensure that the incarcerated population, correctional officers, healthcare workers and personnel working in state, federal and private facilities are protected from COVID-19 exposure. REFORM will work with each state to identify specific PPE needs and allocate them accordingly.

In the wake of a pandemic that has hit marginalized communities more harshly, and ongoing protests after the death of George Floyd, this seems like a ripe time for criminal justice reform philanthropy to kick into high gear. The REFORM Alliance is among a number of new nonprofits that have emerged in this space in recent years. Launched in 2019 by internet entrepreneur Michael Rubin and rappers Jay-Z and Meek Mill, the organization has already secured endorsements and funding from a range of big names in business, entertainment and philanthropy, including Laura Arnold, Robert F. Smith, Daniel Loeb and Meek Mill himself. (See our past coverage here.)

The REFORM Alliance has also partnered with Madonna’s Ray of Light Foundation, Cash Warren’s apparel company Pair of Thieves, New York Times bestselling author Shaka Senghor, the Bail Project, the Dosberg Fund, Operation LIPSTICK and #cut50 to send and distribute 200,000 surgical masks to Rikers Island, the Tennessee Department of Corrections, and several other incarceration facilities.

“I’m grateful REFORM exists,” Dorsey said. “The criminal justice system needs to change. COVID-19 adds to the injustices, and REFORM is best suited to help.”

Cash Warren, meanwhile, said that “helping others has always been part of our DNA at Pair of Thieves… so when the team from REFORM outlined how quickly COVID-19 has spread amongst the incarcerated and those who work in and around prisons, we knew we had to help.”

What is it about REFORM that has attracted big-time donors like Dorsey and others? And what can other nonprofits, particularly organizations working in criminal justice reform, learn from this model?

A Focus on Policy

In a recent conversation, Bob Pilon, REFORM Alliance president and chief growth officer, said, “Policy change is our ultimate objective. The only way we’re going to get 1 million people out of community supervision in the next few years is through really smart policies. We’ve seen widespread bipartisan support for this, and that’s been sort of our mission.”

Having served in leadership positions at Malaria No More and the ONE Campaign before coming to REFORM, Pilon is big on numbers. He notes that there are about 2.3 million incarcerated Americans. Of that total, there are roughly 95,000 people incarcerated for technical probation violations, such as being late to a probation appointment or filing inaccurate paperwork. “We’ve always kind of shunned the prison population. At scale, it just hasn’t really been thought about,” Pilon says.

In addition to raising more widespread awareness of the incarcerated population, one of the purposes of REFORM is to address the even greater number of Americans on probation or parole—another 4.5 million people. While these forms of supervision by the criminal justice system are heavily used as an alternative to incarceration, reform advocates argue that the conditions imposed are often so restrictive that the system sets people up to fail, fueling incarceration.

In Georgia alone, some 404,000 individuals were on probation in 2018, according to a study by Prison Policy Initiative, accounting for the bulk of the 527,000 state residents behind bars or criminal justice supervision. “These are startling numbers. Many are in for very minor technicalities, and yet stuck in the system. We need to increase this awareness of what’s happening through creative means, partnerships, other public-facing ways of engagement,” Pilon explains.

The Right Time

Pilon has known Dorsey since his days at ONE and Malaria No More. And when Dorsey’s Start Small announcement hit earlier this year, Pilon thought the idea of backing REFORM’S work would resonate with him. As the pandemic has swept through the country, America’s jails and prisons have remained top hotspots. The number of prison inmates known to be infected with COVID-19 has doubled during the past month to more than 68,000, and prison deaths tied to the virus have also risen by 73 percent since mid-May, according to the New York Times.

“If you look at the numbers, prisons and jails are super-accelerators of the virus—some 70 or 80% infection rates. And even if someone doesn’t have a heart and says, ‘I don’t care about people living in prisons,’ they should care about the 400,000 people working in prisons every day. This pandemic does not end until we end it inside prisons. We’ve got healthcare workers, guards, corrections officers, other staff going back into their family and their communities,” Pilon says.

With the COVID-19 crisis, REFORM is looking at new ways to make their case, including hammering on the fact that locking people up is incredibly expensive. Pilon explains that the U.S. spends $80 billion on corrections each year, far more than any other country. “So as we go into states and look at supervision bills, we can say by doing this, you’re going to save millions per year. This is much more attractive than maybe it was a few years ago. If they don’t want to raise revenue, they’re going to have to trim the cost,” Pilon says.

So far, with Dorsey’s $10 million donation, REFORM is working with 18 states to get PPE into prisons and jails. REFORM also aims to get more people released early, with an emphasis on low-risk prisoners with fewer than six months left on their sentences, and people who are elderly or have underlying health conditions. “We fundamentally believe that prison should not be a death sentence,” Pilon adds.

At the same time, REFORM is on the lookout for more philanthropic champions and advocates. “We want really great donors who’ve made giving part of their life,” Pilon says. One edge this group has is that it’s not a typical public policy organization, and has already drawn in an eclectic mix of backers.

REFORM recently partnered with creative agency Droga5 to develop #AnswertheCall, a short PSA that amplifies the voices of real people behind bars. Dorsey himself committed to promoting the video, urging his followers to sign a petition and calling for elected officials to enact legislative change. With highly public figures like REFORM CEO Van Jones and rapper Jay Z joining the call to action, leveraging media seems to be another part of REFORM’s early strategy.

Ultimately, Pilon reminds me that criminal justice reform funding doesn’t even attract $500 million a year, yet it affects tens of millions of people. But despite living in a polarized era, he is optimistic that this funding area will broaden its appeal and inspire a range of donors. “Sure, there’s the criminal justice perspective, but there’s the sustainable families and safe communities perspective, as well,” he says.

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