Whoever wins the race to become the next Manhattan district attorney will take over one of the most contentious, highest-profile criminal investigations in the office’s history: the inquiry into former President Donald J. Trump and his business.
Two of the leading candidates in the Democratic primary field, Alvin Bragg and Tali Farhadian Weinstein, have had past contacts with Mr. Trump’s administration — dealings that could become an issue if one of them becomes district attorney.
Mr. Bragg, a former official with the New York attorney general’s office, reminds voters frequently that in his former job, he sued Mr. Trump’s administration “more than a hundred times.”
Ms. Farhadian Weinstein, who once served as general counsel to the Brooklyn district attorney, has been less vocal about Mr. Trump. She only occasionally notes her involvement in a successful lawsuit against the Trump administration. And she has not spoken publicly about once interviewing with Trump administration officials for a federal judgeship early in his term.
Mr. Bragg and Ms. Farhadian Weinstein are among eight Democratic candidates vying to replace Cyrus R. Vance Jr., the district attorney, who is not running for re-election. With the primary less than one month away, Mr. Trump continues to loom over the race.
Mr. Vance’s office recently convened a grand jury that will hear evidence about Mr. Trump and his company, according to a person with knowledge of the matter — a sign that the investigation could soon intensify.
Mr. Bragg and Ms. Farhadian Weinstein have raised more money than any of their opponents, and both say they have the prosecutorial experience to take over the office.
But each would also bring particular experiences to the Trump investigation that the former president, based on his past actions, seems likely to weaponize against them: Mr. Bragg’s history of legal conflict with Mr. Trump and Ms. Farhadian Weinstein’s previously undisclosed discussion of a judicial post with Trump administration lawyers.
Andrew Weissmann, a former senior prosecutor under Robert S. Mueller III, the special counsel who investigated Russian interference in the 2016 presidential election, said he expected Mr. Trump to target the next district attorney just as he had attacked Mr. Mueller, whom the former president had called a “true Never Trumper” and “totally conflicted.”
“No matter who gets elected, he’s going to do opposition research, and assuming an indictment’s brought or anything close to that, he’s going to do what he did with the special counsel,” Mr. Weissmann said.
The impaneling of a new grand jury, first reported by The Washington Post, follows years of investigation by Mr. Vance, who has focused on possible financial crimes at the Trump Organization, including tax and bank-related fraud.
Prosecutors were already using grand juries to issue subpoenas, obtain documents and hear some testimony, but the new grand jury is expected to hear from a range of witnesses in the coming months. There is no indication that the investigation has reached an advanced stage or that prosecutors have decided to seek charges against Mr. Trump or his company.
Mr. Trump’s advisers have said that he will try to impugn the motives of the prosecutors investigating him. After The Post’s report came out, Mr. Trump called the inquiry “purely political” and said that “our prosecutors are politicized.”
That is an attack that he might wield against Mr. Bragg, who has repeatedly brought up his many lawsuits against Mr. Trump and his administration, referring to a period in 2017 to 2018 when he served as a senior official under successive New York attorneys general, Eric Schneiderman and Barbara D. Underwood.
Mr. Bragg, at a Democratic candidate forum in December, cited that lawsuit as one reason he was qualified to oversee the district attorney’s Trump investigation.
“I have investigated Trump and his children and held them accountable for their misconduct with the Trump Foundation,” Mr. Bragg said. “I know how to follow the facts and hold people in power accountable.”
Mr. Bragg acknowledged that Mr. Trump could seek to make an issue of his history if he wins. Asked how he would contend with accusations of bias from the former president, Mr. Bragg said he had been attentive to what he had said publicly — and what he had not said.
“It is a fact that I have sued Trump more than a hundred times,” Mr. Bragg said. “I can’t change that fact, nor would I. That was important work. That’s separate from anything that the D.A.’s office may be looking at now.”
A spokeswoman for Ms. Farhadian Weinstein, Jennifer Blatus, accused Mr. Bragg of attacking Mr. Trump “for political advantage every chance he gets,” in contrast to what Ms. Blatus characterized as her candidate’s “judicious approach.”
In an emailed statement, Ms. Farhadian Weinstein explained her reluctance to speak about a potential attack on her by Mr. Trump.
“I have repeatedly declined requests to discuss a hypothetical argument that a current subject of an investigation in the Manhattan D.A.’s office might make — that’s the only proper approach for open matters the next D.A. will inherit,” she said.
She also criticized Mr. Bragg for hosting a fund-raiser with Daniel S. Goldman, a former House lawyer who worked on Mr. Trump’s first impeachment.
Ms. Farhadian Weinstein’s meeting with Trump administration lawyers over the judgeship occurred in 2017, early in the Trump administration.
A friend of Ms. Farhadian Weinstein, the Harvard Law School professor Noah Feldman, suggested her as a candidate for a district court judgeship to Avi Berkowitz, then a special assistant to Jared Kushner, Mr. Feldman said. He did so on his own initiative, he said. (Two years later, in 2019, Mr. Feldman testified against Mr. Trump at his first impeachment hearing.)
Ms. Farhadian Weinstein, who had previously applied for a judgeship during the administration of President Barack Obama, received a phone call from the Trump administration out of the blue, she told an associate. It is not unusual for lawyers with judicial aspirations to seek judgeships regardless of political party — Ms. Farhadian Weinstein has been registered as both an independent and a Democrat in recent years — and she took the meeting at the Eisenhower Executive Office Building on the White House grounds.
But the meeting, which included lawyers John Bash and Gregory G. Katsas from the White House Counsel’s Office, became heated during a disagreement over constitutional law, the associate said, and the conversation never went further.
A former administration official who was familiar with the meeting did not remember its being characterized as heated and called it a “perfunctory” interview set up to appease the former president’s son-in-law.
A person close to Mr. Kushner said that while Mr. Kushner would periodically pass along to the White House Counsel’s Office recommendations people would make for judges, he has no memory of Ms. Farhadian Weinstein being discussed. There is no evidence Mr. Trump personally knew of Ms. Farhadian Weinstein’s interest in a judgeship or of her trip to meet with the White House lawyers.
While Ms. Farhadian Weinstein’s interview for a judgeship in 2017 could become fodder for the former president’s political attacks should she become district attorney, legal experts said it raised no ethical concerns, nor would it require that she recuse herself from the office’s investigation into Mr. Trump and his organization.
Susan Lerner, the executive director of Common Cause New York, a good government advocacy group, said in an interview that while Ms. Farhadian Weinstein would not have been required to disclose the meeting publicly in the district attorney’s race, the information was “certainly relevant to the job she’s applying for.”
“It’s information that voters will want to consider, and it’s up to them to decide how this factors into their ultimate choice,” Ms. Lerner said.
William K. Rashbaum and Benjamin Protess contributed reporting and Susan Beachy contributed research.