Valerie Jarrett and John Legend

It may not be the most uplifting of conversations or obvious ones, but it was one of the more buzzy discussions at Town & Country’s Philanthropy Summit on Tuesday.

Held on the 44th floor of Hearst Tower in New York, the chat featured former senior adviser to the Obama administration Valerie Jarrett and singer John Legend, both of whom recounted stories about fighting for criminal justice reform.

But Legend wasn’t simply there to talk about his work; the artist was unveiling an initiative called “Unlocked Futures.” The venture, which is with New Profit and Bank of America, is an accelerator program to help formerly incarcerated entrepreneurs.

“What are we going to do to make sure people get the skills they need if they are incarcerated so that when they are released to hit the ground running? And what are we all going to do to give people who’ve earned a second chance, a second chance? That is our focus,” said Jarrett, before turning to Legend’s organization. “He’s really leaning in and launching a very important initiative that I think will help compliment efforts — whether they move forward or they don’t — in Washington.”

Legend reminisced a bit about his relationship with Jarrett, recalling that he met her at the Jefferson Jackson dinner in Iowa when Obama, then a senator, was a “long shot for the Democratic nomination.”

The singer spoke about his other organization, “Free America,” which is focused on “ending mass incarceration.”

“I kind of kicked it off in an informal way when I accepted an Oscar for ‘Glory.’ I wrote this song for the film ‘Selma,’ which commemorated Dr. Martin Luther King Jr.’s march for voting rights, and also just commemorating the work of a great man, who along with many other activists, fought for freedom and justice and equality in this country,” he said. “I didn’t want to get up on stage and get this award and not say something about the continuing fight for justice, equality and freedom in America right now. A lot of that fight is being fought in our criminal justice system right now.”

When he gave his speech, he got some flack for saying, “We are the most incarcerated country on Earth.”

“People were shocked that I said that,” Legend said. “They didn’t actually believe that I was correct. They were like ‘this celebrity doesn’t know what he’s talking about.’ I was fact-checked by The Washington Post and everybody. It turns out that I was telling the truth.”

Legend described the damage that does on families and communities and underscored the importance of working with local legislators. The point, he said, is to invest in better communities, nutrition, education and health and child care, instead of investing in “locking people up.”

To illustrate the state of the current criminal justice system, Jarrett told a story from her days working for Obama, in which she met a young man who was incarcerated and was accused of a crime that took place while he was in prison.

He pled guilty even though it was impossible that he committed the crime because he was told there were eyewitnesses.

“President Obama said, ‘but you had an iron-clad alibi,’ and he said, ‘well, my lawyer told me I probably will get convicted,'” Jarrett said. “How hopeless and how much lack of confidence did that young man have in our system that he pled guilty to a crime he simply couldn’t have committed and had the best excuse in the world?”

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