DA’s Secret Weapon May Be Lawyer Who’s Dogged Trump for Years

A little-known lawyer in New York has long been the thorn in Donald Trump’s side, pressing deeper with every passing year by taking down his scammy charity, blocking his presidential policies, investigating his finances, grilling his annoyed son with questions, and finally indicting the former president last month.

Matthew Colangelo, after years of relentlessly aggressive work, is finally on Trump’s personal radar—and that of his most combative MAGA allies, who’ve painted a target on his back in recent weeks.

Colangelo, who pursued Trump while at the New York Attorney General’s Office, joined the Department of Justice after Trump’s exit from the White House. He recently left the DOJ to join Manhattan District Attorney Alvin Bragg’s team of prosecutors pursuing criminal charges against Trump that threaten to brand him the first-ever American president-turned-felon. And now he’ll be instrumental in prosecuting the DA’s case against Trump.

As such, Colangelo faces the same violent threats that have inundated the DA’s office ever since it decided to arrest Trump. But he’s being singled out.

Manhattan DA Sues Rep. Jim Jordan to Stop ‘Intimidation’

Trump zeroed in on Colangelo in a Truth Social post on Monday, April 3, breathlessly labeling him “a top Democrat DOJ official.” Right on cue, House Judiciary Committee Chairman Jim Jordan (R-OH) fired off a letter to Colangelo later that week making an unprecedented request that the prosecutor—who’s actively working on an open criminal investigation—show up to testify and explain “the circumstances and chain of events that led to your hiring” by the DA, breathing life into the conspiracy theory that President Joe Biden is behind the Trump indictment in New York City.

Media Matters has since documented how MAGA acolytes have gone into a frenzy, with right-wing media darlings spreading that conspiracy with Colangelo as the proverbial missing link.

The DA’s Office declined to make Colangelo available for an interview for this story. However, a close look at his two decades of legal work reveals a man who embodies a zeal for progressive civil rights and pushed Congress for fair housing prices for Blacks, a particularly pertinent point given that he’s now prosecuting a real estate tycoon who once engaged in illegal housing discrimination against African Americans—and routinely lied about the values of his own properties.

But Colangelo’s record also tells the story of a lawyer who somehow found himself at the epicenter of Trump’s legal troubles from the moment Trump sought the presidency.

“I had the opportunity to work with Matthew at the New York Attorney General’s Office. He is a fantastic lawyer, committed to serving the public interest, and of the utmost integrity,” said Jeffrey Novack, who fought alongside Colangelo in a legal battle against the Trump administration’s Securities and Exchange Commission.

How Two Manhattan DA Classmates Hold Trump’s Fate in Their Hands

Colangelo worked as a human rights researcher at an anti-apartheid group in South Africa and as a Boston management consultant before attending Harvard Law School, according to a college announcement for a keynote speech he made there. He later served as a law clerk to then-Appellate Judge Sonia Sotomayor, who is now one of the few remaining liberal justices on the Supreme Court.

Colangelo then became the director of “economic justice” at the NAACP’s legal defense and educational fund, where he took on discrimination cases. One in particular stands out, because it brought him before a congressional subcommittee in 2009 where he stressed the damage that unfair real estate prices can cause. In that case, an $11 billion post-Hurricane Katrina housing recovery program linked “housing assistance to the depressed values of black families’ pre-storm, segregated housing.”

After that, Colangelo spent seven years at the DOJ’s civil rights division, where his team managed to block Texas in 2012 from implementing a voter ID law.

But it was only after Trump won the presidency that Colangelo began to make his life hell. In late 2017, Colangelo became the New York AG’s top “social justice” lawyer—notably backfilling a role left by Alvin Bragg, his future boss at the Manhattan DA’s Office.

And that’s where Colangelo promptly sank his teeth into Trump.

In June 2018, Colangelo’s team sued to dismantle the business executive’s charity, the Trump Foundation, for being “little more than a checkbook for payments” that seemed like a mere extension of his personal business. They eventually won, after the AG’s lawyers proved that Trump illegally used his charity to fund then-Florida AG Pam Bondi. The charity was dissolved after a state judge found Trump had “breached his fiduciary duty.”

But Colangelo soon used his authority at the AG’s office to thwart the federal government’s hard right turn.

The Daily Beast reviewed thousands of court documents that show the extent of Colangelo’s involvement in monumental constitutional challenges to Trump’s vision for America. As the New York AG’s chief counsel for federal initiatives, Colangelo was involved in 32 lawsuits ranging from immigration and civil rights to health care and state tax breaks. He challenged Trump’s attempts to strip DACA legal protections for young, undocumented “dreamers” who were brought to the United States as children—while simultaneously fighting to keep Trump’s 2020 census from inquiring about a person’s citizenship.

Manhattan DA Insiders Worry the Trump Hush Money Case Is Weak Sauce

Indeed, Colangelo’s record in court reads like an entirely separate indictment—against Trump for nearly every policy imaginable. And it dates back to the former president’s very first day at the White House.

Trump signed a day-one executive order to kneecap the Affordable Care Act by limiting consumer protections from a huge chunk of the health insurance market, and in 2018 Colangelo led a multi-state lawsuit that cited his tweets and his stated desire to “let Obamacare explode.” It ended with a clear victory when a federal judge halted the Trump administration.

When Trump’s Agriculture Department in 2018 suddenly halved the amount of whole grains school kids would be served at breakfast and eliminated a cap of salt, Colangelo in New York again led the multi-state fight against the Trump administration. A parallel lawsuit stopped the USDA in its tracks.

When Trump’s anti-immigration rhetoric manifested in a new rule that would suddenly consider a migrant’s use of Medicaid and food stamps to determine whether they should be allowed into the United States, Colangelo was New York’s top-named lawyer in a three-state lawsuit to block it. The Biden administration eventually dropped the policy last year.

Not every battle was victorious. When Trump’s pro-corporate Labor Department in 2019 undid an Obama policy that required electronic collection of work-related injury data, Colangelo represented New York as one of several states challenging that rule. But a federal judge ended up siding with the Labor Department’s ability to manage its own affairs.

However, it was toward the end of the Trump administration that Colangelo moved from tackling Trump’s policies to aiming at Trump himself.

In the summer of 2020, Colangelo emerged as a key investigator probing the Trump Organization’s business practices. Months of law enforcement subpoenas and interviews had discovered what AG Letitia James would later call “significant evidence” of fraud: a decades-long pattern of overvaluing Trump-branded properties to score better bank loans, preferred insurance policies, and bigger tax breaks on donated land.

But in the closing months of the Trump administration, the president’s multi-billion-dollar company was refusing to turn over documents that Colangelo, and his fellow assistant attorneys general, had requested. So they asked a New York state judge to intervene, and Justice Arthur F. Engoron forced the company to respond. In short order, Engoron compelled one of Trump’s sons, Eric Trump, to show up for a deposition.

The Trump Organization Finds a Way to Keep Its 2022 Finances Secret

Colangelo was the one who led the all-day virtual call with Eric Trump on Oct. 5, 2020, grilling the family company executive with questions on what he knew about his dad’s bogus-looking financial statements, seemingly unverified property appraisals, and a huge conservation easement for their forested estate north of the city.

When the Trump son refused to answer basic questions—launching into a minutes-long diatribe about how the AG had “weaponized her office to target my father”—Colangelo cut him off several times.

“I can’t spend the entire day with this sort of obstreperous answer,” Colangelo shot back.

The 48-page legal memo Colangelo signed back then—detailing investigators’ interest in particular properties and the elder Trump’s financial statements—served as a preview of the gargantuan $250 million lawsuit James eventually filed four years later seeking to tear apart the Trump Organization and bleed it dry.

But Colangelo wouldn’t see that through. On Biden’s first day in office, the incoming DOJ brass appointed Colangelo as acting associate attorney general overseeing several law enforcement divisions. And after nearly two years in one of the most coveted leadership positions in the legal field, his former colleague Bragg convinced Colangelo to join him at the Manhattan DA—an office that had long been working on a parallel criminal case about Trump’s business records in parallel to the one Colangelo did back at the New York AG’s office.

On April 4 in Manhattan criminal court, Colangelo was sitting at the desk alongside two fellow prosecutors when the former president sauntered to the defense table. After years of battling Trump’s policies, his corporations, and his refusal to turn over evidence, Colangelo finally had the man himself—before a judge.

Read more at The Daily Beast.

Get the Daily Beast's biggest scoops and scandals delivered right to your inbox. Sign up now.

Stay informed and gain unlimited access to the Daily Beast's unmatched reporting. Subscribe now.