WASHINGTON — Three months before the 2016 election, a small group gathered at Trump Tower to meet with Donald Trump Jr., the president’s eldest son. One was an Israeli specialist in social media manipulation. Another was an emissary for two wealthy Arab princes. The third was a Republican donor with a controversial past in the Middle East as a private security contractor.
The meeting was convened primarily to offer help to the Trump team, and it forged relationships between the men and Trump insiders that would develop over the coming months — past the election and well into President Trump’s first year in office, according to several people with knowledge of their encounters.
Erik Prince, the private security contractor and the former head of Blackwater, arranged the meeting, which took place on Aug. 3, 2016. The emissary, George Nader, told Donald Trump Jr. that the princes who led Saudi Arabia and the United Arab Emirates were eager to help his father win election as president. The social media specialist, Joel Zamel, extolled his company’s ability to give an edge to a political campaign; by that time, the firm had already drawn up a multimillion-dollar proposal for a social media manipulation effort to help elect Mr. Trump.
The company, which employed several Israeli former intelligence officers, specialized in collecting information and shaping opinion through social media.
It is unclear whether such a proposal was executed, and the details of who commissioned it remain in dispute. But Donald Trump Jr. responded approvingly, according to a person with knowledge of the meeting, and after those initial offers of help, Mr. Nader was quickly embraced as a close ally by Trump campaign advisers — meeting frequently with Jared Kushner, Mr. Trump’s son-in-law, and Michael T. Flynn, who became the president’s first national security adviser. At the time, Mr. Nader was also promoting a secret plan to use private contractors to destabilize Iran, the regional nemesis of Saudi Arabia and the Emirates.
After Mr. Trump was elected, Mr. Nader paid Mr. Zamel a large sum of money, described by one associate as up to $2 million. There are conflicting accounts of the reason for the payment, but among other things, a company linked to Mr. Zamel provided Mr. Nader with an elaborate presentation about the significance of social media campaigning to Mr. Trump’s victory.
The meetings, which have not been reported previously, are the first indication that countries other than Russia may have offered assistance to the Trump campaign in the months before the presidential election. The interactions are a focus of the investigation by Robert S. Mueller III, the special counsel, who was originally tasked with examining possible Trump campaign coordination with Russia in the election.
Mr. Nader is cooperating with the inquiry, and investigators have questioned numerous witnesses in Washington, New York, Atlanta, Tel Aviv and elsewhere about what foreign help may have been pledged or accepted, and about whether any such assistance was coordinated with Russia, according to witnesses and others with knowledge of the interviews.
The interviews, some in recent weeks, are further evidence that special counsel’s investigation remains in an intense phase even as Mr. Trump’s lawyers are publicly calling for Mr. Mueller to bring it to a close.
It is illegal for foreign governments or individuals to be involved in American elections, and it is unclear what — if any — direct assistance Saudi Arabia and the Emirates may have provided. But two people familiar with the meetings said that Trump campaign officials did not appear bothered by the idea of cooperation with foreigners.
A lawyer for Donald Trump Jr., Alan Futerfas, said in a statement that “prior to the 2016 election, Donald Trump Jr. recalls a meeting with Erik Prince, George Nader and another individual who may be Joel Zamel. They pitched Mr. Trump Jr. on a social media platform or marketing strategy. He was not interested and that was the end of it.”
The August 2016 meeting has echoes of another Trump Tower meeting two months earlier, also under scrutiny by the special counsel, when Donald Trump Jr. and other top campaign aides met with a Russian lawyer after being promised damaging information about Hillary Clinton. No evidence has emerged suggesting that the August meeting was set up with a similar premise.
The revelations about the meetings come in the midst of new scrutiny about ties between Mr. Trump’s advisers and at least three wealthy Persian Gulf states. Besides his interest in Saudi Arabia and the Emirates, Mr. Mueller has also been asking witnesses about meetings between White House advisers and representatives of Qatar, Saudi Arabia’s bitter rival.
A lawyer for Mr. Zamel denied that his client had carried out any campaign on Mr. Trump’s behalf. “Neither Joel Zamel, nor any of his related entities, had any involvement whatsoever in the U.S. election campaign,” said the lawyer, Marc L. Mukasey.
“The D.O.J. clarified from Day 1 that Joel and his companies have never been a target of the investigation. My client provided full cooperation to the government to assist with their investigation,” he said.
Kathryn Ruemmler, a lawyer for Mr. Nader, said, “Mr. Nader has fully cooperated with the special counsel’s investigation and will continue to do so.” A senior official in Saudi Arabia said it had never employed Mr. Nader in any capacity or authorized him to speak for the crown prince.
Mr. Prince, through a spokesman, declined to comment. The White House did not respond to a request for comment.
Crown Prince Mohammed bin Zayed al-Nahyan of Abu Dhabi, the de facto ruler of the United Arab Emirates, and Crown Prince Mohammed bin Salman of Saudi Arabia, the king’s main adviser, had long opposed many of the Obama administration’s policies toward the Middle East. They resented President Barack Obama’s agreement with Iran over its nuclear program, his statements of support for the Arab Spring uprisings and his hands-off approach to the Syrian civil war.
News outlets linked to Saudi Arabia and the United Arab Emirates fiercely criticized Mrs. Clinton, Mr. Trump’s Democratic opponent, when she was secretary of state, and diplomats familiar with their thinking say both princes hoped for a president who would take a stronger hand in the region against both Iran and groups like the Muslim Brotherhood.
Mr. Nader had worked for years as a close adviser to Crown Prince Mohammed of Abu Dhabi, and Mr. Zamel had worked for the Emirati royal court as a consultant as well. When Mr. Trump locked up the Republican presidential nomination in early 2016, Mr. Nader began making inquiries on behalf of the Emirati prince about possible ways to directly support Mr. Trump, according to three people with whom Mr. Nader discussed his efforts.
Mr. Nader also visited Moscow at least twice during the presidential campaign as a confidential emissary from Crown Prince Mohammed of Abu Dhabi, according to people familiar with his travels. After the election, he worked with the crown prince to arrange a meeting in the Seychelles between Mr. Prince and a financier close to President Vladimir V. Putin of Russia.
Companies connected to Mr. Zamel also have ties to Russia. One of his firms had previously worked for oligarchs linked to Mr. Putin, including Oleg V. Deripaska and Dmitry Rybolovlev, who hired the firm for online campaigns against their business rivals.
Mr. Deripaska, an aluminum magnate, was once in business with the former Trump campaign chairman Paul Manafort, who has pleaded not guilty in the special counsel investigation to charges of financial crimes and failing to disclose the lobbying work he did on behalf of a former president of Ukraine, an ally of Mr. Putin. Mr. Rybolovlev once purchased a Florida mansion from Mr. Trump.
Mr. Nader’s visits to Russia and the work Mr. Zamel’s companies did for the Russians have both been a subject of interest to the special counsel’s investigators, according to people familiar with witness interviews.
Mr. Zamel and Mr. Nader were together at a Midtown Manhattan hotel at about 4 p.m. on the afternoon of Aug. 3 when Mr. Nader received a call from Mr. Prince summoning them to Trump Tower. When they arrived, Stephen Miller, a top campaign aide who is now a White House adviser, was in Donald Trump Jr.’s office as well, according to the people familiar with the meeting.
Mr. Prince is a longtime Republican donor and the brother of Betsy DeVos, the education secretary, and Mr. Prince and Mr. Nader had known each other since Mr. Nader had worked for Blackwater as a business agent in Iraq in the years after the American invasion. Mr. Prince has longstanding ties to the Emirates, and has frequently done business with Crown Prince Mohammed.
Mr. Prince opened the meeting by telling Donald Trump Jr. that “we are working hard for your father,” in reference to his family and other donors, according to a person familiar with the meeting. He then introduced Mr. Nader as an old friend with deep ties to Arab leaders.
Mr. Nader repeatedly referred to the Saudi and Emirati princes as “my friends,” according to one person with knowledge of the conversation. To underscore the point, he would open his mobile phone to show off pictures of him posing with them, some of which The New York Times obtained.
Mr. Nader explained to Donald Trump Jr. that the two princes saw the elder Mr. Trump as a strong leader who would fill the power vacuum that they believed Mr. Obama had left in the Middle East, and Mr. Nader went on to say that he and his friends would be glad to support Mr. Trump as much as they could, according to the person with knowledge of the conversation.
Mr. Zamel, for his part, laid out the capabilities of his online media company, although it is unclear whether he referred to the proposals his company had already prepared. One person familiar with the meeting said that Mr. Nader invited Donald Trump Jr. to meet with a Saudi prince — an invitation the younger Mr. Trump declined. After about half an hour, everyone exchanged business cards.
“There was a brief meeting, nothing concrete was offered or pitched to anyone and nothing came of it,” said Mr. Mukasey, the lawyer for Mr. Zamel.
By then, a company connected to Mr. Zamel had been working on a proposal for a covert multimillion-dollar online manipulation campaign to help elect Mr. Trump, according to three people involved and a fourth briefed on the effort. The plan involved using thousands of fake social media accounts to promote Mr. Trump’s candidacy on platforms like Facebook.
There were concerns inside the company, Psy-Group, about the plan’s legality, according to one person familiar with the effort. The company, whose motto is “shape reality,” consulted an American law firm, and was told that it would be illegal if any non-Americans were involved in the effort.
Mr. Zamel, the founder of Psy-Group and one of its owners, has been questioned about the August 2016 meeting by investigators for the special counsel, and at least two F.B.I. agents working on the inquiry have traveled to Israel to interview employees of the company who worked on the proposal. According to one person, the special counsel’s team has worked with the Israeli police to seize the computers of one of Mr. Zamel’s companies, which is currently in liquidation.
In the hectic final weeks of the campaign and during the presidential transition, several of Mr. Trump’s advisers drew Mr. Nader close. He met often with Mr. Kushner, Mr. Flynn and Stephen K. Bannon, who took over as campaign chairman after Mr. Manafort resigned amid revelations about his work in Ukraine.
In December 2016, Mr. Nader turned again to an internet company linked to Mr. Zamel — WhiteKnight, based in the Philippines — to purchase a presentation demonstrating the impact of social media campaigns on Mr. Trump’s electoral victory. Asked about the purchase, a representative of WhiteKnight said: “WhiteKnight delivers premium research and high-end business development services for prestigious clients around the world. WhiteKnight does not talk about any of its clients.”
After the inauguration, both Mr. Zamel and Mr. Nader visited the White House, meeting with Mr. Kushner and Mr. Bannon.
At that time, Mr. Nader was promoting a plan to use private contractors to carry out economic sabotage against Iran that, he hoped, might coerce it to permanently abandon its nuclear program. The plan included efforts to deter Western companies from investing in Iran, and operations to sow mistrust among Iranian officials. He advocated the project, which he estimated would cost about $300 million, to American, Emirati and Saudi officials.
Last spring, Mr. Nader traveled to Riyadh for meetings with senior Saudi military and intelligence officials to pitch his Iran sabotage plan. He was convinced, according to several people familiar with his plan, that economic warfare was the key to the overthrow of the government in Tehran. One person briefed on Mr. Nader’s activities said he tried to persuade Mr. Kushner to endorse the plan to Crown Prince Mohammed in person on a trip to Riyadh, although it was unclear whether the message was delivered.
Asked about Mr. Nader’s plans to attack Iran, the senior Saudi official said Mr. Nader had a habit of pitching proposals that went nowhere.
Mr. Nader was also in discussions with Mr. Prince, the former head of Blackwater, about a plan to get the Saudis to pay $2 billion to set up a private army to combat Iranian proxy forces in Yemen.
Since entering the White House, Mr. Trump has allied himself closely with Saudi Arabia and the Emirates. His first overseas trip was to Riyadh. He strongly backed Saudi and Emirati efforts to isolate their neighbor Qatar, another American ally, even over apparent disagreement from the State and Defense Departments.
This month, Mr. Trump also withdrew from an Obama administration nuclear deal with Iran that both Saudi Arabia and the United Arab Emirates had campaigned against for years, delivering them their biggest victory yet from his administration.
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