Trump Likened to Mob Boss John Gotti in Ex-Prosecutor’s New Book

Donald J. Trump grew his business, fortune and fame “through a pattern of criminal activity,” according to a new book by a veteran prosecutor, who reveals that the Manhattan district attorney’s office once considered charging the former president with racketeering, a law often used against the Mafia.

The prosecutor, Mark F. Pomerantz, resigned in protest early last year after the newly elected district attorney, Alvin L. Bragg, decided not to seek an indictment of Mr. Trump at that time. By then, the inquiry was more narrowly focused on whether the former president had fraudulently inflated the value of his assets to secure loans.

But for months beforehand, Mr. Pomerantz had mapped out a wide-ranging possible case against the former president under the state racketeering law, according to the soon-to-be published book, “People vs. Donald Trump.” That broader approach was based on the theory that Mr. Trump had presided over a corrupt business empire for years, a previously unreported aspect of the long-running inquiry.

Mr. Pomerantz and his colleagues cast a wide net, examining a host of Trump enterprises — including Trump University, his for-profit real estate education venture, and his family charitable foundation.

“He demanded absolute loyalty and would go after anyone who crossed him. He seemed always to stay one step ahead of the law,” Mr. Pomerantz, a prominent litigator who has prosecuted and defended organized crime cases, writes of Mr. Trump. “In my career as a lawyer, I had encountered only one other person who touched all of these bases: John Gotti, the head of the Gambino organized crime family.”

A lawyer for Mr. Trump recently sent Mr. Pomerantz a letter threatening that, “If you publish such a book and continue making defamatory statements against my clients, my office will aggressively pursue all legal remedies.”

The book, a copy of which was obtained by The New York Times, is a chronicle of the complicated and circuitous investigation, which produced charges against Mr. Trump’s longtime chief financial officer and his family business, but has yet to yield formal accusations against the former president himself.

Mr. Pomerantz’s book arrives as the investigation is ramping up once again, with prosecutors impaneling a new grand jury to hear evidence about Mr. Trump’s role in paying hush money to a porn star, Stormy Daniels, during the 2016 presidential campaign. Mr. Bragg’s administration, which has raised ethical and legal concerns about Mr. Pomerantz’s revealing details of the inquiry, is also applying additional pressure on the former chief financial officer, Allen H. Weisselberg, seeking to secure his cooperation against the former president.

The developments represent a significant escalation of the investigation and suggest that Mr. Bragg is again nearing a decision about whether to charge Mr. Trump.

A year ago, in the early weeks of his tenure, Mr. Bragg balked at indicting Mr. Trump for a case centered on the potentially fraudulent inflation of his assets. Although Mr. Bragg’s predecessor, Cyrus R. Vance Jr., concluded that he had enough evidence to make that case, Mr. Bragg was concerned that there was insufficient proof that Mr. Trump intended to break the law, a necessary element of the case.

His decision to pull back just as the investigation was reaching a crescendo prompted the resignation of Mr. Pomerantz — and another senior prosecutor overseeing the investigation, Carey R. Dunne — and the final chapters of the book detail that mounting tension with Mr. Bragg.

Mr. Pomerantz blames Mr. Bragg for being too slow to get up to speed on the case after he was elected in November 2021. Mr. Bragg, he writes, also failed to forge a personal relationship with Mr. Pomerantz and Mr. Dunne. And the district attorney was distracted with other public relations headaches as he faced a fusillade of opposition to his unveiling of new policies aimed at limiting incarceration for certain defendants.

In a statement in response to questions about the book, Mr. Bragg defended his decision.

“After closely reviewing all the evidence from Mr. Pomerantz’s investigation, I came to the same conclusion as several senior prosecutors involved in the case, and also those I brought on: More work was needed,” he said.

He added: “Our skilled and professional legal team continues to follow the facts of this case wherever they may lead, without fear or favor. Mr. Pomerantz decided to quit a year ago and sign a book deal. I haven’t read the book, and won’t comment on any ongoing investigation because of the harm it could cause to the case.”

In the wake of Mr. Pomerantz’s departure, The New York Times published his resignation letter, which cast a harsh light on Mr. Bragg’s decision not to pursue an indictment of Mr. Trump. In the book, Mr. Pomerantz also cites a scathing email he sent Mr. Bragg, admonishing him for his perceived lack of engagement.

“Neither Carey nor I are rash, immature, starry-eyed young lawyers,” Mr. Pomerantz wrote in the email. “You need to respect our judgment, our decades of experience as prosecutors and defense lawyers, and the work that we have put into the case.”

Mr. Pomerantz’s book offers new details about the evidence he and other prosecutors had assembled, including information provided by a bank employee who had approved financing for Mr. Trump’s company.

Still, there was substantial disagreement in the district attorney’s office about the strength of the case, which Mr. Pomerantz acknowledges, and several prosecutors stepped away from it, rather than continue down the path that Mr. Pomerantz was pursuing. And some pundits have questioned whether the case could be successful in showing that Mr. Trump had knowledge of any fraud.

In the book, Mr. Pomerantz argues that the investigation “turned into the legal equivalent of a plane crash,” adding that the cause of this crash was “pilot error.” But despite disagreeing with Mr. Bragg’s decision, he disputed accusations from some Trump critics who theorized that Mr. Bragg was corrupt, writing that “suggestions that Alvin acted in bad faith were ridiculous.”

Asked to respond to Mr. Pomerantz’s “pilot error” line, Mr. Bragg said in his statement, “Mr. Pomerantz’s plane wasn’t ready for takeoff.”

The book has deepened the wound between the two prosecutors. Mr. Bragg’s office recently sent a letter to Mr. Pomerantz and his publisher, Simon & Schuster, saying that the author had been obligated to obtain permission from the office before publicizing certain information about the investigation, and that he had not done so.

“This office believes there is a meaningful risk that the publication will materially prejudice ongoing criminal investigations,” the letter said, adding that were Mr. Pomerantz to reveal grand jury material, he could be charged with a felony because such information is by law secret, and that profiting from his work as a public servant in New York City might also be illegal.

In response, Simon & Schuster said that it stood behind the book, and Mr. Pomerantz writes in the book that he did not “prejudice any investigation or prosecution of Donald Trump” or reveal grand jury information.

The office also says that Mr. Pomerantz was bound by a nondisclosure agreement he signed in late 2020 when he was consulting on the case. Mr. Pomerantz says that the agreement was not binding after he formally joined the office in early 2021.

The book’s description of conversations between Mr. Pomerantz and Mr. Bragg’s team could arguably complicate the investigation.In particular, Mr. Pomerantz detailed Mr. Bragg’s opposition to using Michael D. Cohen, a longtime fixer for Mr. Trump who turned on the former president, as a witness, an awkward disclosure now that Mr. Cohen may become one of Mr. Bragg’s star witnesses.

At one meeting in February of last year, as Mr. Pomerantz and Mr. Dunne were seeking to allay the new district attorney’s fears about the valuations case, Mr. Bragg commented that he “‘could not see a world’ in which we would indict Trump and call Michael Cohen as a prosecution witness,” Mr. Pomerantz writes.

A spokeswoman for the district attorney’s office said that four people who were present at the meeting disputed that recollection.

Some of Mr. Bragg’s aides also attacked Mr. Cohen’s credibility and penchant for media leaks. At a meeting, Mr. Pomerantz writes, one of Mr. Bragg’s senior prosecutors played a recording of a recent media appearance Mr. Cohen made in which he crowed about his importance as a witness in the case. The disclosures could provide ammunition to Mr. Trump’s lawyers as they attacked Mr. Cohen’s credibility.

The book’s narrative covers Mr. Pomerantz’s yearlong detachment to the district attorney’s office, where Mr. Vance lured him out of retirement to work exclusively on the Trump investigation. Mr. Pomerantz offered to work for free.

When he came on board, Mr. Pomerantz inherited what he saw as a “floundering” investigation. He soon drilled down on the hush money, exploring whether money laundering was involved.

He developed concerns, however, that such a case was too risky under New York law, leading him to focus on the potential racketeering case. New York State’s version of the federal racketeering statute, known as enterprise corruption, “was an ideal vehicle for prosecuting Donald Trump and the Trump Organization,” Mr. Pomerantz writes. Mr. Vance called the idea “bold” but other members of the team appeared unenthusiastic.

By Labor Day 2021, the racketeering theory became too ambitious to sustain. Mr. Vance planned to leave office at the end of the year, and wanted to make a decision about whether to charge Mr. Trump before he stepped down as district attorney.

As the investigators narrowed the focus to whether Mr. Trump inflated the value of his hotels, golf clubs and office buildings, Mr. Pomerantz relied on the New York attorney general’s office for help.

Mr. Pomerantz explains that the attorney general, Letitia James, and her investigators, had been “way ahead of” the district attorney’s office and that he became a “raving lunatic” about getting the two agencies to work together.

“The information we received from the attorney general’s office would become hugely important,” he writes.

When Mr. Bragg took over in early 2022, Mr. Pomerantz told him that the case was not a slam dunk, but that he was nonetheless confident they could secure a conviction of Mr. Trump, putting their chance of success at roughly 70 percent.

Ultimately, he writes, he ran into a “cautious and conservative culture” at the district attorney’s office and among the prosecutors working on the investigation.

Now that Mr. Bragg has returned to the hush money case, Mr. Pomerantz writes that indicting Mr. Trump for that alone “would be a very peculiar and unsatisfying end to this whole saga.”