The Manhattan district attorney’s office is prosecuting two criminal cases that come uncomfortably close to Mayor Eric Adams, bringing unwanted attention to the administration and raising questions about Mr. Adams’s relationships with the accused.

One involves Mr. Adam’s former buildings commissioner, who has been charged in a sealed indictment with corruption-related crimes, according to two people familiar with the investigation who asked for anonymity to discuss sealed charges.

In the other, six people — including a longtime friend of the mayor, Dwayne Montgomery — were charged with conspiring to illegally funnel money to Mr. Adams’s mayoral campaign in 2021.

The cases have subjected the mayor’s associates — and to a degree, Mr. Adams himself — to the scrutiny of the Manhattan district attorney, Alvin L. Bragg. While there is no suggestion that Mr. Adams is under criminal investigation, the cases are not the first to place the mayor, who touts his law-and-order credentials, in the awkward position of having to explain his conduct or that of his associates.

Since taking office in January 2022, the mayor also has been linked with a Brooklyn pastor known as the “bling bishop” who was charged with fraud and extortion and to twin brothers who share a criminal history involving money laundering.

In the most recent case, the sealed indictment against the mayor’s former buildings commissioner, Eric Ulrich, Mr. Adams has faced questions about his relationship with the former agency head.

Mr. Ulrich resigned in November 2022, days after investigators with the district attorney’s office seized his phone and he was questioned by prosecutors. He told them that months earlier, Mayor Adams had warned him that he was the focus of a criminal investigation, two of the people said. (Mr. Ulrich’s comments to prosecutors were first reported by The Daily News.)

Mr. Adams has denied that he gave any warning, which would not appear to violate state laws in any event. A spokesman for Mr. Adams said in a statement Thursday that the mayor had not received any requests from the Manhattan district attorney regarding either Mr. Ulrich or the straw donor case.

“The mayor hasn’t spoken to Mr. Ulrich or Mr. Montgomery about either of the respective investigations, either before or after they became public,” he said.

In recent weeks, a grand jury voted to charge Mr. Ulrich with having accepted a discounted apartment from a real estate developer who has had business before the city, the people said. Mr. Ulrich accepted at least some of the benefit while he was still in charge of the agency. The Brooklyn-based developer, Mark Caller, is also charged in the indictment, the people said.

The charges also touch on what prosecutors are expected to characterize as Mr. Ulrich’s ties to organized crime, the people said. The indictment is likely to be announced by Mr. Bragg in September.

A lawyer for Mr. Ulrich, Samuel M. Braverman, said last month that until he saw the charges in an indictment, he would not comment. On Thursday, he said he had nothing to add.

Mr. Caller’s lawyer, Benjamin Brafman, said he had not seen the indictment but that he expected it to include an allegation that Mr. Ulrich received a discounted apartment in one of Mr. Caller’s buildings.

“That is patently false,” Mr. Brafman said. “He paid market rate without any discount whatsoever,” Mr. Brafman said, adding that Mr. Ulrich had rented the apartment before becoming buildings commissioner.

Last month, Mr. Bragg announced the indictment of the six people who he said had recruited and reimbursed individual donors to Mr. Adams’s campaign in order to illegally obtain more money from the city. The lead defendant is Mr. Montgomery, a retired Police Department inspector, longtime friend of the mayor and a former colleague on the force. Prosecutors said that the defendants had sought to influence the administration.

According to court papers filed by the district attorney’s office, Mr. Montgomery and Rachel Atcheson, a close aide to Mr. Adams, set up a fund-raisers at which straw donors gave the campaign $250 apiece. Neither Ms. Atcheson nor Mr. Adams have been accused of wrongdoing.

New York City has a matching funds program designed to dilute the influence of big donors that rewards campaigns for donations of up to $250 from residents. For every personal donation of that amount to a mayoral campaign, the city gives a campaign $2,000.

The mayor, a retired police captain, campaigned as a tough-on-crime candidate who would restore order to New York City in the wake of the pandemic. In a Monday news conference, Mr. Adams said that he would not be distracted by the case against Mr. Ulrich.

“The D.A. has his job,” he said. “I have my job.”

Mr. Bragg, who like Mr. Adams was elected in 2021, has studiously avoided direct confrontation with the mayor, and the two men maintain a cordial relationship. But the district attorney, a former federal prosecutor who handled public corruption cases, has said he wants his office to pursue investigations into the powerful.

A spokeswoman for Mr. Bragg declined to comment on either of the cases.

Mr. Ulrich told prosecutors that Mr. Adams’s warning was delivered during a brief meeting in 2022, the people said. Beforehand, the mayor asked Mr. Ulrich to hand his phone to an associate, they said.

Then, as the two men talked, Mr. Adams warned Mr. Ulrich to “watch your back and watch your phones,” according to the people. Mr. Ulrich, they said, later told prosecutors that he understood the mayor to mean that he was a focus of a criminal investigation.

At the Monday news conference, Mr. Adams said that he had not even known that Mr. Ulrich was under criminal investigation.

Mr. Adams has shown few qualms about maintaining ties with people who have been accused of wrongdoing. He appointed Mr. Ulrich to head the buildings department despite a letter Mr. Ulrich had written four years earlier on behalf of a constituent with mob ties, and despite Mr. Ulrich’s acknowledged gambling and alcohol addictions.

The mayor also remains close with Johnny and Robert Petrosyants, twin brothers who pleaded guilty to financial crimes in 2014 and have continued to engage in a pattern of questionable business dealings, according to a New York Times investigation.

“I’m going to talk with people who have stumbled and fell,” Mr. Adams has said of the Petrosyants. “Because I’m perfectly imperfect, and this is a city made up of perfectly imperfect people.”

Supporters and members of the Adams administration are not Mr. Bragg’s only recent City Hall targets: His prosecutors are pursuing a third case, which focuses on the administration of Mr. Adam’s predecessor, Bill de Blasio.

The district attorney’s office is expected, in the coming weeks, to unveil charges against Howard Redmond, the head of Mr. de Blasio’s security detail. Mr. Redmond has been accused of blocking an investigation into the misuse of the detail by Mr. de Blasio, including bringing his security team on unauthorized city-financed trips related to his failed 2020 presidential bid.


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