Last June, the man credited with introducing President Donald Trump to his wife asked the administration for a favor.

Paolo Zampolli, a former modeling agent turned presidential special envoy, had learned that his Brazilian ex-girlfriend was in a Miami jail, arrested on charges of fraud at her workplace. They had been in a custody battle over their teenage son. Now he saw an opportunity.

He reached out to a top official at Immigration and Customs Enforcement, explaining that his ex was in the country illegally, according to records obtained by The New York Times and a person familiar with the communications. Could she be put in ICE detention? That could help him get his son back.

The official, David Venturella, promptly called the agency’s Miami office to ensure that ICE agents would pick up the woman from the jail before she was released on bail, according to the records and a person with knowledge of the conversation who requested anonymity to discuss it. During the call, Venturella noted that the case was important to someone close to the White House.

The woman, Amanda Ungaro, was placed in ICE custody and ultimately deported, an outcome that may well have happened regardless of Zampolli’s meddling. But the ICE official’s willingness to spring into action for a Trump ally — even one in a low-level, largely ceremonial role — reflects a recurring theme of the second Trump administration: The levers of the federal government can be pulled to settle a personal score.

Zampolli, 56, is known in Washington for flaunting his proximity to the Trumps. In this case, he used his clout to solicit help from an agency beset by allegations of unlawful overreach.

In an interview with the Times, Zampolli denied asking ICE to detain Ungaro or seeking any other favors. He said he merely asked Venturella to explain what was going on with her case.

The Department of Homeland Security, which oversees ICE, said in a statement that Ungaro was detained and deported because she was on a long-expired visa and had been charged with fraud. “Any suggestion that she was arrested and removed for political reasons or favors is FALSE,” the statement said.

As the president’s special representative for global partnerships, Zampolli is a minor character in Trump’s Washington. But the role keeps him within photo-op range of the Trump family, Cabinet secretaries and other prominent figures in and around the administration.

He throws parties at a sprawling D.C. town house where the walls are hung with pictures of him and the president, and an end table displays a copy of the first lady’s book, “Melania.”

His Instagram feed shows him trailing behind Melania Trump at the United Nations, standing beside the president’s chief of staff and posing with Trump’s son-in-law Jared Kushner. “I am honored to have been a friend of the President for more than 30 years, a friend of the First Lady for 29 years,” reads one caption. It ends: “Loyalty is king.”

Zampolli and Trump were fixtures of New York City nightlife in the 1990s and, as Zampolli told the Times a decade ago, shared a common interest: “We both like beautiful things.”

For years, the men have told the story of how, one night at the Kit Kat Club in 1998, Zampolli introduced Trump to Melania Knauss, a model he had recruited from Slovenia.

In the city’s modeling scene, Zampolli also intersected with Jeffrey Epstein, the financier who would later be accused of sexually abusing hundreds of girls and young women. The men once discussed buying a modeling agency together, and Zampolli’s name appears several times in the millions of Epstein documents recently released by the Justice Department.

In one 2011 email, Epstein warned an Emirati businessperson: “Be careful, zampoli is trouble. Lots.” He added, “He sells stories to the press.”

Zampolli told the Times in the recent interview that he did not have a close or warm relationship with Epstein, as shown by the fact that he appeared less frequently in the Epstein files than many other figures, including professors, monarchs and celebrities.

“At least I was included, because if you’re not on the list, you’re a loser, right?” he said.

Ungaro was a 17-year-old model when she arrived in New York for the first time in 2002, flying on Epstein’s plane from Paris with her French agent. She never saw Epstein again, she said in an interview. But later that year, she met Zampolli, then 32, at a Manhattan nightclub.

Zampolli wooed her as a client, she said, persuaded her to move to the United States and began a romantic relationship with her that would last two decades. Zampolli said this didn’t happen until Ungaro was 19.

They ascended into elite social circles as Zampolli forged connections to former President Bill Clinton, wealthy businessman Ron Burkle and other prominent figures.

But few of the relationships were as enduring as the one he had with the Trumps.

“I really miss to see both of you,” Zampolli wrote in a 2013 email to Melania Trump reviewed by the Times. “As you know Donald changed my life w/ u That night at dinner w/ Copperfild.” He was referring to an evening a decade earlier when, at a dinner with illusionist David Copperfield, Trump had offered Zampolli a job in real estate.

The two couples remained friends, as Zampolli and Ungaro both secured ambassadorships to the United Nations, representing Dominica and Grenada.

They would all sit together at New Year’s Eve parties at Mar-a-Lago, Trump’s Florida estate, and Melania Trump would send birthday wishes and presents to their son.

“OMG You are always the best!!!!!! Let’s meet Sooooon XOXO,” Zampolli replied to one of her messages in 2015.

At the tail end of Trump’s first term, Zampolli was appointed to the board of the Kennedy Center. He moved to Washington for a short time with Ungaro and their son.

But by 2023, she was fed up. Zampolli had made headlines for his boisterous parties filled with younger women, and for passing around explicit text messages between himself and a woman he claimed was a sex worker.

Ungaro left Zampolli, moved to Florida and married a doctor from Brazil. Their son went to boarding school and then lived with her, and the former couple fought over custody of him.

Then, last June, Ungaro and her husband were arrested.

The local police, prompted by anonymous tips, had been investigating the couple’s workplace: a medical spa where offerings included Botox and face lifts. Ungaro and her husband were charged with fraud, practicing medicine without a license and other crimes. They pleaded not guilty.

Ungaro’s husband held a green card and was quickly released from jail on bond. But she did not have the same legal status. For years, she told the Times, Zampolli had dangled the prospect of marriage — and the path to citizenship that comes with it — and then taken it back. She held a string of temporary visas, the last of which expired in 2019.

After her arrest, Zampolli began working his connections at ICE.

He sought help from Corey Lewandowski, then a top aide to the Homeland Security secretary, records show. He told the Times that Lewandowski did not respond to him. Lewandowski said he “never heard of that guy,” and the Homeland Security statement said he had “no involvement” in Ungaro’s case.

Zampolli had better luck with Venturella. His back-channeling noted his relationships with the president and first lady, according to the records obtained by the Times and a person familiar with his communications. And he conveyed his belief that Ungaro’s detention would help him gain custody of their son.

Zampolli told the Times that he was not asking Venturella for a favor. “I asked David what was going on because I did not know the process,” he said.

Zampolli said that while he considered the Trumps close friends and noted that they “were always there for me,” he did not recall whether he invoked their names or mentioned that Ungaro’s detainment would help him get his son.

A spokesperson for Melania Trump said in a statement that the first lady “has no knowledge of, nor involvement in, the personal affairs of Mr. Zampolli and Ms. Ungaro.” He also said she “has had no contact or engagement with” ICE.

After Venturella called the Miami office, Ungaro was placed in ICE custody. The local office kept Venturella updated on her status.

People familiar with the outreach said that, in all likelihood, it did not alter the trajectory of Ungaro’s case. She had already been flagged for detention.

But ICE officials have some discretion when deciding whom to detain, and the agency has specific guidance for cases that will affect minors. With detention centers in Florida and elsewhere stretched beyond capacity, some detainees have been released with ankle bracelets while their cases move through immigration court.

When the Times informed Ungaro that a senior ICE official had gotten involved in her case at the behest of Zampolli, she said she was appalled: “It’s devastating that they could have affected what happened to me.”

By September, she said, she had become convinced that if she remained at the detention center, she would lose custody of their son. So she asked the immigration judge to send her back to Brazil, which he did.

In November, the son asked to move to Brazil to live with Ungaro, and Zampolli agreed. But by the end of the year, the teenager decided to move back to the United States to live with his father. He remains there while his parents continue fighting in court.

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This article originally appeared in The New York Times.

By Megan Twohey, Shawn McCreesh and Hamed Aleaziz/Maurizio Fiorino
c. 2026 The New York Times Company