The U.S. Attorney’s Office of the Northern District of Illinois has been in the news a lot lately — and for some disturbing reasons.
The Justice Department has reportedly opened an inquiry into a Chicago-based nonprofit backed by LinkedIn co-founder Reid Hoffman and is considering possible charges of money laundering. According to The New York Times, the inquiry is focused, at least for now, on Hoffman’s nonprofit, American Future Republic, which helped fund certain legal expenses in E. Jean Carroll’s civil cases against President Donald Trump. The U.S. attorney’s office has said it has not opened a criminal investigation into Carroll, the New York writer who accused Trump of sexually assaulting her in the 1990s, although the reporting makes clear that prosecutors are examining the accuracy of statements made during the civil litigation about outside funding.
At this point, even if Carroll is not formally the subject of the investigation, the criminal inquiry looks less like an ordinary money-laundering or perjury investigation than an effort to use federal prosecutorial power to revisit a credibility fight Trump already lost in court.
The lead prosecutor for these investigations is Trump-appointed U.S. Attorney Andrew Boutros. His office made headlines recently over its prosecution of protesters who came to be known as the “Broadview Six.” The cases collapsed amid extraordinary revelations about prosecutors’ conduct before the grand jury.
At this point, even if Carroll is not formally the subject of the investigation, the criminal inquiry looks less like an ordinary money-laundering or perjury investigation than an effort to use federal prosecutorial power to revisit a credibility fight Trump already lost in court.
The office first downgraded from felony charges to misdemeanors and also reduced the number of defendants; last week it dismissed charges against the remaining individuals indicted last October after protesting outside of an Immigration and Customs Enforcement detention facility in Broadview, Illinois. Boutros said in court proceedings that prosecutors’ conduct during the grand jury process led to the dismissal.
The conduct was stunning: Prosecutors reportedly interacted with grand jurors outside normal proceedings, improperly vouched for witnesses, and even removed or sidelined grand jurors viewed as skeptical of the government’s case. At one point, the judge, who noted the conduct was redacted from grand jury transcripts she was shown, remarked that she had never seen such conduct before.
For any U.S. attorney’s office — and especially for one with Chicago’s history and reputation — this was a major institutional embarrassment.
Boutros’ office could be on the verge of another high-profile debacle, even if Carroll is not currently a formal target of the inquiry and the focus remains on American Future Republic.
To be clear, a false statement under oath can matter. But the particulars here make a potential case against Carroll look exceptionally thin — and proving she knowingly lied under oath would be particularly tough.
Carroll testified in 2022 that no one else was paying her legal fees. Her lawyers later disclosed that some expenses were funded by American Future Republic. The funding issue came out before trial, and Trump’s lawyers seized on it. The trial judge barred Trump’s team from introducing that evidence, and the U.S. Court of Appeals for the 2nd Circuit later upheld that ruling. The appellate court noted that Carroll had plausibly represented that she had forgotten about the limited outside funding and that there was no evidence she personally secured the funding, interacted with the funder or even knew the funder’s political position.
Simply put, this was not hidden fraud discovered after the fact.
In 2023, a New York City jury awarded Carroll $5 million in damages after finding Trump liable for sexually abusing her in a department store in 1996 and for later defaming her. In 2024, another jury ordered Trump to pay Carroll $83.3 million in damages. The president has denied wrongdoing and appealed the awards.
Simply put, this was not hidden fraud discovered after the fact; it was disclosed before trial, litigated before the trial court and addressed by the 2nd Circuit.
Ordinarily, federal prosecutors do not convert into criminal investigations collateral credibility fights from civil litigation, especially ones already known to the trial and appellate courts. Then again, the DOJ is not typically led by a lawyer who previously was the president’s personal attorney.
Legally, the Carroll and Broadview Six cases are unrelated. But they point in the same institutional direction: federal prosecutorial power being used not simply to enforce law but to relitigate political conflict through the criminal process.
The broader pattern is hard to ignore because the targets are not random. Consider: James Comey, the former FBI director whom Trump fired and has long blamed for the Russia investigation, has been indicted twice by Trump’s DOJ. Letitia James, the New York attorney general who won the civil fraud case against Trump, was indicted on mortgage-related charges. After that case was dismissed, the DOJ tried — and failed — to secure a new indictment. John Bolton, Trump’s former national security adviser turned public critic, had his home and office searched by the FBI, and he was later indicted under the Espionage Act.
There are more: Sen. Adam Schiff, one of Trump’s central impeachment adversaries, became the subject of a DOJ mortgage-fraud inquiry. Another prominent Trump critic, former Rep. Eric Swalwell, was referred to the DOJ over mortgage and tax allegations. Lisa Cook is facing a DOJ mortgage-fraud probe as Trump tries to remove her from the Federal Reserve, and the Fed received grand jury subpoenas amid an investigation of its then-chairman, Jerome Powell, after Trump publicly attacked the Fed’s renovation project and repeatedly criticized Powell over interest rates.
The through line is unmistakable: federal investigative power being steered again and again toward people who have investigated Trump, sued him, impeached him, contradicted him, restrained him or became symbols of opposition to him.
Patrick Fitzgerald, the former U.S. attorney in Chicago, once embodied a very different prosecutorial culture in the office that’s leading the investigation into American Future Republic. He once told the media about his job: “One day I read that I was a Republican hack. Another day I read that I was a Democratic hack. And the only thing I did between those two nights was sleep.”
That was the old ideal of federal prosecution: Both sides might accuse you of bias, but neither side could plausibly claim you were using the machinery of federal law enforcement as a political instrument.
Today, Fitzgerald — who prosecuted Republicans and Democrats and was respected precisely because he seemed fundamentally indifferent to partisan outcome — represents Comey against the federal government. In seeking the dismissal of Comey’s indictment, Fitzgerald and co-counsel wrote that “President Trump ordered the Department of Justice to prosecute Mr. Comey because of personal spite” and that the indictment arose from “multiple glaring constitutional violations and an egregious abuse of power by the federal government.”
All of these prosecutions suggest the culture Fitzgerald represented — restraint, proportionality, respect for the grand jury, reluctance to turn marginal civil-litigation disputes into criminal cases — is no longer guaranteed, even in the offices most famous for it.
Duncan Levin is a criminal defense attorney and former federal prosecutor who serves as a Lecturer on Law at Harvard Law School and is a frequent contributor to MS NOW.