Trump prosecutor quit top DOJ post for lowly NY job in likely bid to ‘get’ former president, expert says

The prosecutor whose opening statement kicked off the historic trial of Former President Donald Trump left a lofty perch in the Biden administration Justice Department for his current comparatively modest New York City job – a career move that legal analysts describe as puzzling and one that's prompted questions regarding motivation.

Even though Matthew Colangelo is only now sitting in a courtroom formally opposing the former president, his work has for years involved investigating Trump and his businesses, despite working for different prosecutorial offices at varying levels of government. Colangelo's sudden switch from top DOJ official to a role with the DA's office in the Big Apple has particularly raised eyebrows.

"It's very odd. It’s usually the other way around. . . . And frankly, that sounds to me like somebody who thought, 'Ah, here's an opportunity to go and get Donald Trump,'" attorney and former member of the Federal Election Commission, Hans von Spakovsky, told Fox News Digital in a phone interview this month. 

It's rare to see successful, ambitious attorneys willingly climb several steps down the career ladder, experts note.

"It is a little unusual," Heritage Foundation senior legal fellow Zack Smith said of Colangelo’s career moves. "Particularly, the position he had at the Justice Department was a fairly high ranking one . . . he spent some time in the New York Attorney General's office, he also spent some time as a career staffer in the DOJ Civil Rights Division. He was in leadership in the Justice Department, and then immediately from that leadership position - an acting leadership position - went to the DA’s office."

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Colangelo's current case marks the first time a former president has stood trial on criminal charges. It stems from payments made by Trump’s former personal attorney to a former pornographic actress ahead of the 2016 election and was brought forth last year by Manhattan District Attorney Alvin Bragg.

The trial began in earnest this week - after a week of jury selection - as Colangelo delivered his opening on Monday, seeking to make the prosecution's case that Trump had illegally falsified business records to conceal another crime. 

Trump is no fan of Colangelo’s. He has slammed the attorney as a "radical left [prosecutor] who was put into the state working for Letitia James and was then put into the District Attorney’s office to run the trial against Trump." That comment came before the presiding judge, Juan Merchan, imposed a gag order that prevents Trump from speaking publicly about witnesses or the prosecution team. 

Colangelo has a lengthy government resume, working in a variety of legal roles that date to the Obama administration. He most recently served nearly two years in Biden's DOJ, including as acting associate attorney general and overseeing the Antitrust, Civil, Civil Rights, Environment and Natural Resources, and Tax Divisions.

Colangelo's background includes time spent clerking for Supreme Court Justice Sonya Sotomayor when she served on the U.S. Court of Appeals for the Second Circuit and seven years at the NAACP’s legal defense and educational fund. Afterward, Colangelo worked for three years in the DOJ’s civil rights division during the Obama administration. He also served as deputy director of the Obama-Biden Administration’s National Economic Council and as chief of staff at the Labor Department under the Obama administration, the DA's office detailed in a press release. 

Colangelo's decision in 2017 to take a job in the New York Attorney General’s Office – filling a role left vacant by the departure of his future boss, Bragg – led to the first in a series of cases against Trump. 

Colangelo assisted a case in 2018 that dissolved Trump’s former NY-based charity, the Donald J. Trump Foundation, after prosecutors alleged that it had illegally coordinated with Trump’s 2016 campaign. The charity was dissolved after a judge found that Trump had "breached his fiduciary duty."

That same year, Colangelo worked as lead prosecutor in a case involving the Trump administration’s push to include a citizenship question in the 2020 census. The Justice Department ultimately decided to print the 2020 Census without the citizenship question due to lengthy court battles that included having the Supreme Court weigh in that the question could not be added for the time being. 

"I think given his time at the AG's office, in the Justice Department, and now at the district attorney's office, it certainly appears like his career path in the past several years has been designed to target and essentially try to bring charges against Donald Trump in whatever form or fashion he can do so," Smith said.

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Von Spakovsky cited Colangelo's previous employment with the DOJ's Civil Rights Division as a potential concern, calling the DOJ department a home for "some of the most unethical lawyers" he’s ever met. Von Spakovsky worked in the Civil Rights Division from 2001 to 2005 but did not overlap with Colangelo. He spoke to Fox Digital about what he had personally experienced in the office and how he viewed the operation of the office in the years that followed. 

"I've now been a lawyer for four decades. I work at Heritage. I've worked in the federal government. I was in private practice. I was in-house corporate counsel," he said. "I have never in my entire career met lawyers more partisan, more far-left radical ideologues than I met in the Civil Rights Division in the career ranks. 

"I was in the voting section to start with . . . they had about 100 people – half lawyers, about half support staff. I have never in my life been met with the kinds of hostility I was met with when I started my job there."

Von Spakovsky said he believes the reason for his chilly reception was "because they knew that politically I was a conservative," though noting he was a career employee, and not a political appointee.

He pointed to an IG report published in 2013 that detailed concern that the office predominantly hired from "liberal" civil rights organizations, including the ACLU, NAACP and Lawyers’ Committee for Civil Rights under Law, and noted that the report showed "political and ideological hiring going on into the career ranks, which is not supposed to happen."

"Because they're all hired from these liberal advocacy organizations, they never make the transition to understanding that they now are a government lawyer and that their client is the public," he said. "What they all think is, ‘Oh, I used to work for the ACLU. Well, now I can continue doing that work for the ACLU, but I have the power of the government behind me.'"

After moving from the New York AG’s office to the DOJ and then finally to Bragg’s office, Colangelo now finds himself at the heart of the New York v. Trump case unfolding in Manhattan criminal court. 

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The trial’s origins reach back to October of 2016, when Trump’s former personal attorney, Michael Cohen, paid former pornographic actor Stormy Daniels $130,000 to allegedly stop her claims about an alleged extramarital affair she had with the then-real estate tycoon in 2006. Trump has denied having an affair with Daniels. 

Prosecutors allege that the Trump Organization reimbursed Cohen, and fraudulently logged the payments as legal expenses.   

"During the election, TRUMP and others employed a ‘catch and kill’ scheme to identify, purchase and bury negative information about him and boost his electoral prospects," Bragg said last year. "TRUMP then went to great lengths to hide this conduct, causing dozens of false entries in business records to conceal criminal activity, including attempts to violate state and federal election laws."

"Catch-and-kill" schemes are understood as tactics used by media and publishing companies to buy the rights to a person’s story with the intention of burying the information.

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Bragg was elected district attorney in 2021, succeeding Cyrus Vance, who did not run for re-election. Vance left the office with the massive case hanging in the air despite saying he was "committed to moving the case as far along in the decision-making as I can while I’m here." 

Bragg officially took office in January 2022, with the nation wondering whether he would indict Trump. 

By March of that year, however, two prosecutors in the office who were investigating Trump's net worth, Mark Pomerantz and Carey Dunne, resigned. Pomerantz charged that Bragg had stopped pursuing the case against Trump and suspended the investigation "indefinitely."

"You have reached the decision not to go forward with the grand jury presentation and not to seek criminal charges at the present time," Pomerantz wrote in his resignation letter, Fox Digital previously reported. "The investigation has been suspended indefinitely."

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His letter continued: "Of course, that is your decision to make. I do not question your authority to make it, and I accept that you have made it sincerely."

He added, however, that "a decision made in good faith may nevertheless be wrong."

Months later, in December, Bragg announced a new hire: Colangelo. 

"Matthew Colangelo brings a wealth of economic justice experience combined with complex white-collar investigations, and he has the sound judgment and integrity needed to pursue justice against powerful people and institutions when they abuse their power," Bragg said at the time. "Those who would harass tenants, steal wages, endanger workers or defraud the public should know that the Manhattan D.A.’s Office has never had a stronger, more dedicated team in place to enforce our laws and hold them accountable." 

Four months after Colangelo left the DOJ for the DA’s office, Trump was indicted on 34 counts of "falsifying New York business records in order to conceal damaging information and unlawful activity from American voters before and after the 2016 election."

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Falsifying business records is a misdemeanor. Prosecutors are working to prove that Trump falsified records with an intent to commit or conceal a second crime, which would be a felony. This week, prosecutors revealed that the other crime in the case is "conspiracy to promote or prevent election," a violation of New York election law. 

​​Colangelo said during his opening argument on Monday that the case against Trump "is about a criminal conspiracy and a cover-up." He argued that Trump, Cohen and the then-CEO of American Media Inc., David Pecker, had "conspired to influence the 2016 presidential election." Prosecutors say that Pecker had helped to facilitate "catch-and-kill schemes" by purchasing exclusive rights to stories that could have damaged Trump’s run for the White House and then not publishing the stories. 

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"Some of the charges he's trying to bring are false-records charges against Donald Trump, which are ordinarily misdemeanors, unless they were done in furtherance of another felony, simply to cover up another felony," Smith told Fox News Digital. 

Prosecutors say that Trump violated a New York election law, though he had already been examined by federal bodies that oversee elections. The Justice Department in 2019, for example, "effectively concluded" its investigation into Trump’s payments. In 2021, the Federal Elections Commission, the agency dedicated to enforcing campaign finance laws, announced that it had dropped a case looking into whether Trump had violated election laws with the payment to Daniels. 

Von Spakovsky also underscored to Fox News Digital that both the FEC and DOJ had declined to pursue the case. 

"The [FEC] looked at this and said that this settlement was not a violation of federal law. The Justice Department also has criminal enforcement authority over federal campaign finance laws, and the Justice Department has also not considered this a crime," he said. 

Von Spakovsky added that he couldn't speculate whether Colangelo had been hired by the DA’s office for the purpose of prosecuting Trump, but argued that he believed no "objective lawyer" would have carried through with the case. 

"I think any objective lawyer, without any kind of partisan goals, would have taken a look at the facts and the law in this case and would not have decided to go forward," he said. 

Trump’s trial is ongoing and anticipated to last at least six weeks. 

Fox News Digital reached out to the district attorney's office, the White House and the DOJ's Civil Rights Division for comment but did not receive responses.

Fox News Digital's Brooke Singman contributed to this report.