Born in 1953, David Clegg was raised in the New York City borough of Staten Island. Inspired by the civil-rights and anti-war movements of the 1960s and guided by the mentorship of his family’s Lutheran minister, Clegg in his youth planned to someday become an ordained Christian minister who would help people who had somehow lost their moral compass. He recalls, in particular, a defining moment that had occurred when he was 15 years old, when three other teenagers accosted him, stabbed him in the back, and demanded that he give them whatever money he was carrying at the time. “I recovered quickly [from the injury], but [that incident] was very informative for me,” said Clegg in a 2020 interview. “These kids were my age, and they were ready to kill me for the few dollars I had in my pocket. That made me think that wherever these kids came from, it was a very bad place. They were dehumanized somehow, so they were able to dehumanize me… If these kids had been given a chance, they couldn’t have done this to me.”

After earning a bachelor’s degree from the State University of New York in 1974 and a J.D. from the University of Buffalo School of Law in 1977, Clegg became a clerk for the NAACP Legal Defense Fund, where he worked on anti-death-penalty appeals that were argued before the U.S. Supreme Court. He then applied to work for the Peace Corps, but eventually chose instead to become an attorney with Volunteer in Service to America (VISTA) – later renamed AmeriCorps — where he spent four years as a civil-rights lawyer in Nebraska and South Dakota representing Native American groups like the Lakota Sioux.

In 1982, Clegg moved with his wife to the Hudson Valley region of New York State, where he continued practicing mostly civil-rights litigation and criminal defense. Since 1982, he has been the head of his own law firm, David J. Clegg Esq., based in the town of Kingston, New York. For nine years during the 1980s and 1990s, he also worked as a part-time Assistant Public Defender on behalf of low-income individuals.

In addition to his career as an attorney, Clegg has been involved in activism within his local town and church communities. Indeed, he completed a master’s degree program at Yale Divinity School in 2011 and became an ordained deacon within the United Methodist Church in June 2016. He is also the chairman of the Ulster County Human Rights Commission, where, according to the leftwing organization Democracy For America, he “works to stop the school-to-prison pipeline and to defend the rights of immigrants and the civil liberties of the LGBTQ community.” In addition, Clegg served a stint as the Board Vice President for Family of Woodstock, a social services agency based in Ulster County, New York.

In June 2018, Clegg ran for New York State’s 19th Congressional District seat in the U.S. House of Representatives, but finished a distant sixth in a crowded Democratic primary field, garnering only 11% of the vote. The eventual winner of the general election for that U.S. House seat was a fellow Democrat, Antonio Delgado.

In January 2019, Clegg announced his candidacy for Ulster County District Attorney, stating that, if he were to be elected, he would strive to: (a) help end “mass incarceration”; (b) “stop the [racial] disproportionality in our criminal justice system”; and (c) promote “restorative justice,” with a focus on reform and rehabilitation instead of punishment and incarceration. “I had never heard the words ‘restorative justice’ before I took a great ethics class at the Divinity School,” Clegg later recalled in a 2020 interview. “It changed the trajectory of my life.” “Restorative justice focuses on repairing the harm that has been done,” he elaborated. “It starts with the people who committed harmful acts recognizing that what they did hurt somebody. It also ensures that victims participate in what justice should be. In our current system, victims are on the sidelines.”

Amid an ongoing debate regarding bail reform in New York State, Clegg, in an online piece published by the Hudson Valley One newspaper, denounced the existing cash bail system as one that discriminated unfairly against nonwhite minorities and the poor:

“As long as money is a condition of pretrial release, poor and working-class people will remain behind bars while those who are wealthy go home regardless of the likelihood of innocence or guilt. This is a fundamental injustice. The harms of unaffordable cash bail are unequivocal: people lose their jobs, homes and families while detained. Even worse, innocent people sometimes plead guilty just to get out of jail. This is how it works. After spending days or weeks in jail, you — an innocent defendant — are brought back to court and offered the chance to plead guilty for ‘time served.’ You have the option to plead and go free or go back to jail and wait for trial. What choice would you make? […] The purpose of bail is to ensure the appearance of a defendant in court, not to exact punishment before conviction. […] Our district attorney has enormous discretion to implement these changes today and immediately stop the injustices that occur under the cash bail system. … The DA should start by reviewing the cases of every defendant currently held on bail in the Ulster County Jail and release them from pretrial detention unless they pose a risk to public safety.”

In the 2019 election cycle for the Ulster County DA race, Clegg collected over $240,000 in donations through the New York Justice and Public Safety (NYJPS) Political Action Committee, whose founder, the leftist multibillionaire George Soros, provided the entirety of the PAC’s funding. According to InfluenceWatch.com, NYJPS “is the New York branch of the vast ‘Safety and Justice’ network” of state-level PACs that Soros created “to finance the campaigns of progressive Democratic candidates for district attorney in more than a dozen of America’s cities.” At one point in 2019, NYJPS issued a statement describing Clegg as “the only candidate that can be trusted to create a 21st century DA’s office that keeps us safe.”

In October 2019, controversy erupted over a Clegg campaign mailer that prominently featured a photo of Mr. Clegg shaking hands with a well-known, local anti-police activist and convicted felon named Ismail Shabazz, who had been incarcerated from 2016-2018 for selling handguns, sawed-off shotguns, and assault rifles to undercover FBI agents. Hudson Valley One described Shabazz as a man who: (a) “routinely refers [on social media] to cops as ‘PIGS,’ an acronym for ‘Police in Gangs’”; (b) “has accused individual police officers — without providing evidence — of everything from drug abuse to rape”; (c) has “associated with radical black nationalist groups, including the New Black Panther Party” (NBPP); (d) “helped form an offshoot of the [NBPP] dubbed ‘Black Panthers for Self Defense’” in 2014; (e) attended a 2014 rally in support of Assata Shakur, the infamous Black Liberation Army member and Marxist who murdered New Jersey state trooper Werner Foerster in the 1970s; and (f) told an undercover FBI informant about his wish to recruit members of the Bloods street gang into his political organization and to use firearms against police officers.

Objecting to the criticism he received regarding the photo in the mailer, Clegg declared: “I had nothing to do with it. I didn’t choose that photograph, nor would I have.” But his Republican opponent in the race for DA, Michael Kavanagh, said that members of the law-enforcement community were: (a) “wondering why someone who wants to be the chief law enforcement officer in the county is associating with somebody who refers to cops as pigs and was recorded selling weapons while expressing the hope they’ll be used on cops,” and (b) “wondering why somebody like Shabazz supports Clegg.”

When the November 5, 2019 Ulster County District Attorney election was over, Kavanagh led Clegg by a mere 3 votes, a razor-thin margin that automatically triggered a recount of the roughly 1,300 absentee and affidavit ballots that had been cast. After that recount was completed on December 11, Clegg was ahead by 77 votes — 26,331 to 26,254. That recount was followed by a variety of legal challenges and audits prompted by Kavanagh, and the final election results were not officially announced until January 2020. Reflecting on his narrow victory, Clegg said: “This election was a change in many ways. I was a progressive candidate, and instead of the usual ‘law and order’ platform, I was talking about mass incarceration, systemic racism, and things that make people uncomfortable.”

When Clegg formally took office in January 2020, he became the first Democrat to serve as Ulster County District Attorney since 1850. In one of his earliest statements as DA, he again advocated in favor of eliminating the existing state cash bail system: “I do think the law should be tweaked. I think there should be an amendment. [Democratic New York State Senator] Jen Metzger has introduced a bill, I’ve joined in introducing the bill, which I think will help…The key is we don’t want to be putting people in prison because they are poor. We don’t want them laying about in prison; we want them out in their community.”

In December 2021, the Ulster County newspaper Daily Freeman reported that under Clegg, the county was experiencing “a local surge in weapons-related crimes” that amounted to a “real gun pandemic” in the community.

In January 2022, Clegg voiced his support for alternatives to incarceration for defendants struggling with drug addiction: “We want to help addicts, not just throw them in jail and hope when they got out they learned their lesson.”