Minutes after a New York judge ordered the Trump Organization to pay $1.6 million for criminally dodging taxes last Friday, Manhattan District Attorney Alvin Bragg held a press conference.
It was short—two minutes, to be exact—but Bragg was still able to bask in the glory of his office’s hard-fought victory against Donald Trump’s family company. And he was able to tease his next move.
Bragg congratulated his team on successfully prosecuting two Trump companies and sending its top accountant to jail, noting how the win “closes this important chapter of our ongoing investigation into the former president and his business.”
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“We now move on to the next chapter,” he continued.
To many, it sounded like Bragg was finally ready to set his sights on former President Donald Trump—nearly a year after making the disastrous decision to not indict him for fear of losing in court, a move that demoralized the investigative team and caused its top two prosecutors to quit in protest.
But Bragg may finally have changed his mind.
The recent trial offered a preview of the damning evidence that ties Trump directly to the crime. First, there’s the memo Trump signed approving chief operating officer Matthew Calamari’s blatantly illegal request in 2012 to reduce his taxed salary by $72,000 to cover the cost of his untaxed high-end corporate apartment. Add to that the fact that Trump, in a separate New York legal fight in 2021, asserted under oath that he personally oversaw Calamari’s compensation.
Second, there are checks Trump signed to cover the expensive tuition at a private school for chief financial officer Allen Weisselberg’s grandkids. Add to that Weisselberg’s trial testimony, in which he remembered being in Trump’s office a decade ago when he promised to pay it back—a vow he fulfilled when he reimbursed the company by also lowering his taxed salary.
Third, there’s the star witness who was never used at the Trump corporate trial: Jennifer Weisselberg, the divorced mother of two who’s currently battling for custody of her kids—the ones whose school tuition Trump covered. Jennifer Weisselberg has repeatedly told prosecutors she was in the room with Trump himself when he discussed the executive compensation scheme that artificially lowered taxed salaries on the books.
Then again, the next chapter could be another criminal case entirely. This investigation started under the previous district attorney, Cy Vance Jr., as a look at Trump’s hush money payment to porn star Stormy Daniels—a transaction that was laundered through his company to hide what were clearly 2016 presidential campaign expenses to avert a public relations disaster.
“This case has tentacles,” said Duncan Levin, a former prosecutor at that very office who now represents Jennifer Weisselberg and has been in touch with investigators.
When asked by journalists, the Manhattan District Attorney’s Office wouldn’t clarify what exactly Bragg meant by “the next chapter.” But former prosecutors who spent decades in that office say they’ve seen this before, and the natural next step is to finally go after the boss himself.
“For people who want a certain outcome—to go after Trump—it gives hope. They’re going to be thorough. I’m doubtful he would have said ‘next chapter’ if they weren’t looking,” said Catherine A. Christian, who oversaw financial fraud investigations as an assistant district attorney there.
“It happens all the time with large, complex investigations,” she said, recalling how her team worked on major international narcotics cases in phases.
The best-known examples come from mob takedowns—a clichéd comparison at this point but still fitting, given how Trump spent decades running a tax cheating real estate company that fakes business records but keeps employees quiet by cultivating a culture of unquestionable loyalty for the man whose name is embossed on every building he owns.
“You start at the bottom and you work your way up,” said attorney John Moscow, who spent years at the Manhattan DA’s Office prosecuting complicated financial fraud investigations.
But Manhattan prosecutors going after the Trump Corporation and Trump Payroll Corporation ran into the same problem they encounter during mob takedowns—particularly the ones that experts say they face when targeting the Russian mafia: unbending loyalty.
During the recent criminal trial against the Trump companies, they were simply unable to flip employees against their boss.
The most embarrassing example came when prosecutors tried to prove the company knowingly faked business records by questioning company controller Jeffrey S. McConney on the witness stand, where he assumed the role of a clueless accountant. McConney testified that he was unable to identify the most basic tax rules or payroll functions.
By contrast, he thoughtfully answered every question posed by company defense lawyers. The disparity was so stark that at one point during the trial, Justice Juan Merchan voiced his concern that the state’s witness was actually going out of his way to protect his employer, which pays him nearly half a million dollars a year.
But as visibly frustrated as prosecutors were—nearly labeling McConney a hostile witness—they couldn’t simply turn the heat on him. That’s because they had built their criminal case against the Trump companies in part by having him testify before the grand jury that issued the indictment, a process that in New York oddly gives a suspect total immunity about anything they discuss during their testimony. McConney was safe the minute he became a witness, even if he had nothing useful to say at trial.
“It’s hard to fault a prosecutor for that. Sometimes you have to give immunity to an unsavory person to go after somebody who’s worse… for the higher good, for the bigger fish,” Christian said.
Meanwhile, Weisselberg didn’t flip either. Once he changed lawyers and hired former Manhattan prosecutor Nicholas Gravante, he scored a plea deal that let him vastly reduce his sentence at Rikers Island—and only admit to his own crimes at trial. His lawyer has repeatedly asserted that Weisselberg “won’t testify against anyone whose last name is Trump.”
So much of the case against Trump depends on flipping his lieutenants, said former Manhattan prosecutor Jeff Chabrowe.
“They didn’t flip, and they failed,” he said of Trump employees and the investigators. “They tried to do everything they could, and in the end, they got a truncated thing here where they went after the organization and Weisselberg. And there's this fine that’s pretty weak.”
Several former prosecutors expressed dissatisfaction over Bragg’s reluctance to indict Trump already, questioning why his team still hasn’t done it.
“I struggle to see why they charged Allen Weisselberg and not Trump—and not other people,” Levin said. “The only critical distinction is that one of them was president of the United States.”
One former prosecutor lamented how the current iteration of that office isn’t sticking to the aggressive culture it’s famous for. It was an ethos embodied in an office wisecrack—a sort of mantra, if you will—that prosecutors would say to push back against the dread that accompanied taking on cases that the DA’s office may lose: “Fuck ’em if they can’t take a joke.”
But former assistant district attorneys also leave open the possibility that Bragg’s “next chapter” has as much hope of coming to fruition as George R. R. Martin’s final installment of Game of Thrones.
“Bragg is probably giddy about how much good publicity he's gotten about this. He's being lauded as one of the first major victories against Trump, when in fact it's really just kind of a little watered-down version of what it was supposed to be,” Chabrowe said. “He drew first blood on Trump, and he’s going to quit while he’s ahead.”
“If he was going to go after Trump, he would have,” he added.
Whatever Bragg does, he’ll likely have to make a decision soon if he wants to remain relevant. Trump simultaneously faces indictments from separate, more advanced investigations that threaten to derail his 2024 campaign for president.
Fulton County District Attorney Fani Willis is probing the way Trump intimidated a Georgia elections official, and Department of Justice Special Counsel Jack Smith is investigating whether Trump broke the law by spreading the Big Lie and hoarding classified documents after leaving the White House. Whoever strikes first, wins.
“Bragg is competing with other, more resourceful prosecutors,” Chabrowe told The Daily Beast. “Obviously Trump has been incredibly successful at avoiding prosecutions thus far—criminally, civilly. I do think he’s going down. But Bragg, who’s already had a lot of negative publicity and does not have the most experienced people there… I don’t see them being the ones who’d eventually be successful in finally knocking him off.”
