In 1991, Damon Chetson, a University of Pennsylvania freshman and Daily Pennsylvanian staff writer, covered the murder of a Penn student that Philadelphia police pinned on 21-year-old Chester Hollman III.

Twenty-seven years later, the Conviction Integrity Unit formed by Philadelphia’s controversial new district attorney, Larry Krasner, found evidence of police and prosecutorial malfeasance and concluded that Hollman’s guilt was “near-impossible.” By 2020, Hollman had been freed and awarded a $9.8 million settlement.

As a candidate for Wake County district attorney this year, Chetson has suggested dedicating prosecutors to review previous convictions and sentences, as well as police misconduct allegations, something incumbent Lorrin Freeman says the office lacks the resources to do.

Chetson, the son of a Philadelphia schoolteacher, didn’t plan on becoming a lawyer when he was at Penn. He certainly didn’t imagine becoming a self-styled progressive reformer. He was an anti-war, anti-drug-war history student enthralled by libertarian intellectuals like Hayek, Friedman, and Nozick.

After graduating in 1994, he pursued a Ph.D. in European history at the University of Virginia, but gave up before writing his dissertation. (He earned a master’s instead.) With—as he describes it—“no practical skills,” Chetson secured a position managing seminars and scholarships at the Institute for Humane Studies at George Mason University, a Charles Koch-funded think tank.

In 2004, he became vice president of the Barry Goldwater Institute, a conservative Arizona outfit, where, among other things, he decried taxes and proposals for city-funded high-speed internet. He says he was quickly disenchanted.

“I was coming into contact with people that were very, very anti-immigration,” Chetson said. “When you get down to where the rubber meets the road, very racist at certain levels—not the institute, but some of the people around it, the donor types.”

He started law school at Arizona State in 2007, then transferred to UNC a year later. (His now-wife got a job in the Triangle.) He says he planned to do corporate law until he interned at the public defender’s office and, while shadowing another lawyer, confirmed a client’s alibi just before his trial for armed robbery.

“It was like putting together a puzzle,” Chetson said. “Then to get the actual not-guilty was so much better. There’s an incredible rush.”

After graduating in May 2009—at age 37, with $90,000 in debt—Chetson had no job prospects, so he set up his own shop, pairing with more experienced lawyers while he built his practice.

All the while, he was a registered Republican. As recently as 2014, he voted in Republican primaries, records show. But Chetson says his politics had already started to evolve. He supported Barack Obama in 2008 and says he would have in 2012, except he didn’t vote. (While Chetson endorsed Freeman for clerk of superior court in 2010, he also skipped that election.) The emergence of Donald Trump led him to quit the Republican Party, he adds.

But what he saw as a criminal defense attorney pushed him to the left, he says.

“There are structural problems in the United States,” Chetson said. “Sometimes those are expressed through a structure that has racist outcomes. Part of that is economic—there is vast inequality in this country. And structural racism is expressed sometimes in the criminal justice system. One only needs to go down and look at the Wake County Justice Center to see who fills up the courtrooms. Oftentimes, it’s our Black and Brown neighbors. Being a criminal defense attorney has helped me understand that fact.”

By 2020, Chetson was a donor to and volunteer for Sen. Bernie Sanders’ campaign for president. Sanders’ loss was disappointing, Chetson says. But it also made him think about running for office.

“There are two ways of winning a campaign,” he said. “The one way is to actually win the campaign, which is obviously what I intend to do. But the other way to win a campaign is to raise issues that you think are very important, and to have those issues reach a broader audience.”

His campaign’s most prominent issues have been cannabis and the death penalty. He also says that, under the Second Chance Act, he’d expunge the records of many 16- and 17-year-olds and end policies that criminalize poverty.

In addition, Chetson faults Freeman for her office’s high turnover. Asked what he would do differently, he says he’d ask Wake County to fund additional prosecutors, like Mecklenburg County does for its district attorney’s office.

“I don’t expect the Republican legislature, or even a Democratic legislature, to be like, ‘Oh, we’ll give you a million dollars,’” Chetson said. “But something’s got to change.”

The county already pays more than $7 million a year for the City-County Bureau of Investigation, which means Freeman doesn’t have to rely on the state crime lab.

“If the legislature ultimately does not meet the demand, we will not have enough resources,” Freeman said. “But I think we collectively have chosen to continue to push the legislature to meet the demand. They have the resources to do what’s right.”

Sig Hutchinson, who chairs the Wake County Board of Commissioners, points out that the DA’s office isn’t alone in its predicament. The public defender’s office is about two-dozen positions short of what a 2019 study said it needed.

“There’s so many ways that we could improve the systems,” Hutchinson said. “But it’s so broken, so underfunded. Where do you start?”

In interviews, Chetson sometimes has a firmer grip on what he thinks is wrong than how he’ll fix it, which he attributes to Freeman’s lack of transparency. “So it’s hard for me to say, well, what would you do to change the office, beyond saying there need to be clear lines of accountability,” he said.

Freeman says Chetson doesn’t understand how the office works or the constraints it’s under. That, she argues, is a weakness.

“Leading an office within the criminal justice system that does the things we’ve talked about—keeps this community safe, but also makes sure that the criminal justice system is fair—is a difficult and complicated job,” she said during a Feb. 15 candidate forum. “I have the experience to do that. He doesn’t.”

Chetson, who has spent the last 11 years in a one-lawyer office, acknowledges that he’s asking voters to put him in charge of the county’s most powerful 43-lawyer firm. But he says he’ll bring in a leadership team with experience in prosecution and managing lawyers.

Also, he’s managed people before: “I was the vice president of a think tank back in ’04.”

Jeffrey Billman reports on politics and the law for The Assembly. He is the former editor-in-chief of INDY Week in Durham. Email him at

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This is a sidebar of The Assembly’s larger exploration of the Wake County District Attorney’s Office. That deep dive is linked here.