Sooner or later it was going to be true. People have been telling aspiring writers to start out as lawyers forever, and it’s terrible advice. But in one case, at least, it worked out.
“Even as a kid, I planned to be a lawyer,” says Reynolds Holding J.D.’82, whose recent book, “Better Judgment: How Three Judges Are Bringing Justice Back to the Courts,” addresses the longtime issue of the eroding power of the judiciary. He admits, though, that he headed toward the law mostly because people convinced him to follow his childhood enjoyment of argument. “And I did like the concept of governance, and the rules,” he says, which comes through clearly in his book about three judges who fiercely defend them.
Yet when he graduated college, he didn’t come directly to Duke Law. “I wanted to do something that was an experience,” he says, “that was unusual.” So he went to Shreveport, Louisiana, and worked for a newspaper. “And I was hooked,” he says. “Finding out why people did what they did, and trying to explain what they were doing, was appealing to me.”
Still, Duke Law beckoned. From there he joined a big New York corporate law firm “because, again, that’s what I was told was the best thing to do.” He sat in the conference rooms and closed the deals but found himself thinking: “What kind of an impact did I really have on society?” So it was back to newspapers.
He ended up at the San Francisco Chronicle, covering courts and legal issues. He expanded to investigative pieces. One series – on the danger of medical syringes during the days of the AIDS epidemic – was a finalist for the Pulitzer Prize.
Thereafter came a long period of successful journalism – Legal Affairs magazine, Time Magazine, ABC News, Reuters. Holding married, had a daughter, moved back to the East Coast. But something was missing. “I always wanted to write a book,” he says. “I had always thought of writing a book as … something that was hard but worthwhile and important – and tested one’s intellect and ability in ways that other things did not.”
Apart from the difficulty of the project was settling on a topic that was worth the effort. Then shortly after the financial crisis of 2008, when Holding was working at Reuters, a New York judge named Jed Rakoff distinguished himself by holding the banks behind the crisis to account. Holding cites Matt Taibbi, who wrote in Rolling Stone: “Federal judge Jed Rakoff … is fast becoming a sort of legal hero of our time.”
Says Holding, “One of these cases came up in a story meeting, and somebody at the meeting said, ‘You know, somebody ought to write a book about this guy.’ And I said, well maybe that’s right.”
And he learned it was true – writing a book is a whole different animal from anything he’d done before. “And I wanted to write a book that was not academic, not a legal book.” The financial crisis was over, so Rakoff couldn’t be the only subject. Holding spoke to agents and editors. “Are there other judges who do this?” one asked. Holding had been covering the law for years, so he found more.
Carlton Reeves, a district judge for the Southern District of Mississippi, welcomed Holding in (as Rakoff did) and shared his story. Reeves, who went to first grade in the first year of desegregated public schools in Mississippi, told Holding that the judges whose unpopular rulings had forced desegregation "were heroes to me.”
Holding also reached out to Martha Vázquez, senior U.S. district judge for the District of New Mexico: “Her father was an undocumented immigrant, and she literally grew up helping her parents pick oranges and garden in rich people’s yards – and brought that empathy to how she viewed the world.”
Currently at home in New York, Holding is a research scholar and editor at Columbia Law School, married to a defense lawyer. His daughter, Carolyn, is an actress. Holding is glad his book, which came out in late 2025, describes “the people who I considered to be doing the real work of the courts, and that’s the trial judges, the district court judges. “These are not judges practicing politics,” he says. “These are judges doing their job.”