As Steve Witkoff, President Trump’s envoy to the Middle East, conducted delicate cease-fire negotiations between Israel and Hamas this year, his son Alex was on another mission. He was quietly soliciting billions of dollars from some of the same governments whose representatives were involved in peace talks with his father.

Alex Witkoff pitched Qatar, a mediator in the Gaza talks and a key U.S. ally in the Middle East, on a planned investment fund focused on commercial real estate projects in the United States, according to a spokeswoman for Qatar’s sovereign wealth fund.

He later wooed prospective investors by telling them that he had already secured pledges of billions of dollars from government-affiliated funds in Qatar, the United Arab Emirates and Kuwait, according to people familiar with his pitches who were not authorized to speak publicly.

The real estate fund had the potential to yield hundreds of millions of dollars of revenue for the Witkoff Group, which Steve Witkoff founded in 1997. He remains a partial owner of the company, after selling a portion of his stake this year.

The contemplated investment fund, as well as Alex Witkoff’s fund-raising outreach to Gulf nations, represents another startling example of the Witkoff family apparently trying to profit off its patriarch’s proximity to the president. Steve Witkoff and his other son, Zach, already face accusations of pushing ethical boundaries through their cryptocurrency venture with the Trump family, which also has been doing deals in the Middle East.

The New York Times reviewed documents about the fund prepared by the Witkoff Group and spoke with people familiar with the pitch to investors. Alex Witkoff was fielding questions about the fund from potential investors as recently as a month ago. But shortly after The Times asked about the fund, Anna LaPorte, a Witkoff Group spokeswoman, said the plans, which she described as “preliminary,” had been shelved. “They are not moving forward with that fund,” she said.

The spokeswoman for the Qatar Investment Authority, Melanie Dunn, confirmed that Alex Witkoff had pitched the sovereign wealth fund but said that after internal discussions it had decided not to buy in.

The news that the Witkoffs recently sought money from the Qataris is the latest example of the family’s entanglements in the region where Steve Witkoff now represents the United States. And while some of the Witkoffs’ financial ties to the Middle East have been public, a Times investigation found that the business relationship with Qatar is more extensive than previously known.

As recently as May, the Witkoff Group received $100 million from a financial trust that is run by the private-equity firm Apollo Global Management and partly owned by Qatar.

The Witkoffs’ relationship with Qatar traces back to the first Trump administration, when the government of the tiny, oil-rich country began using investments to curry favor with people close to Mr. Trump — including Steve Witkoff, The Times found. By the time Mr. Trump was back in the White House, the relationship had evolved, and the Witkoff Group saw Qatar as a go-to source of funding.

“This is another bogus smear from the failing New York Times against Steve Witkoff,” said a White House spokeswoman, Anna Kelly, without citing any factual inaccuracies in the detailed questions that The Times sent seeking comment for this article. She said Mr. Witkoff was “finalizing” the process of divesting from his company.

David Warrington, the White House counsel, said in a separate statement that Mr. Witkoff “takes seriously his compliance with the government ethics rules.”

‘Loyalty Above All Else’

Qatar has used its $557 billion sovereign wealth fund, one of the world’s biggest, to amass global influence, investing in think tanks, universities and lobbying groups. In the United States, one of the focal points has been real estate investments. Since 2014, Qatar has poured more than $4 billion into the Manhattan market alone, buying the Plaza Hotel, the St. Regis and a stake in the Empire State Building, among other properties.

In 2017, Qatar’s campaign for influence nearly came undone. Several Gulf neighbors imposed a blockade, citing the country’s ties to Iran, Hamas and the Muslim Brotherhood. To get it lifted, Qatar sought help from the United States — an uphill battle, because Israel, an important U.S. ally, was deeply suspicious of Qatar. That June, Mr. Trump himself suggested that Qatar was financing “radical ideology” in the Middle East.

Qatar devised a strategy to bolster its American relationships, especially with the Jewish community and people who had Mr. Trump’s ear.

The Qatari Embassy hired Stonington Strategies, a lobbying firm jointly run by Nicolas Muzin, a Republican political strategist, and Joey Allaham, a restaurateur who had built connections with politicians through his kosher restaurants. Their mission: find prominent American Jews willing to vouch for Qatar with federal officials.

Stonington — which would receive nearly $4 million in fees from Qatar in 2017, according to the firm’s federal lobbying disclosures — quickly zeroed in on Steve Witkoff, thanks in part to his friendship with Mr. Trump. The two men, who both started their careers in New York real estate, have been close since the 1980s.

In the fall of 2017, Mr. Allaham, whose Prime Grill restaurant in Midtown Manhattan was a popular venue for power lunches among New York’s observant Jews, prepared a memo for his Qatari bosses.

The memo, which The Times reviewed, described Steve Witkoff as a “confidant” and “unofficial adviser” to Mr. Trump and noted that “the president counts loyalty above all else.” Mr. Allaham added that because Mr. Witkoff is Jewish, a relationship with him would “provide credibility to others in the greater Jewish community.”

The memo suggested that the Qataris invest in Witkoff Group projects. “Real estate has long been an entree to a higher profile and domestic engagement for foreign investors,” Mr. Allaham wrote.

Ali Al-Ansari, a spokesman for the Qatari government, denied trying to cultivate a relationship with Steve Witkoff in order to gain favor with Mr. Trump and noted that Qatar and the United States have long had close ties. “Qatar’s investment decisions are kept entirely separate from diplomacy,” Mr. Al-Ansari added.

Oval Office Access

The timing of the Qatari outreach was ideal. In 2017, Steve Witkoff was facing financial trouble.

His company had recently borrowed $267 million to buy the Park Lane Hotel with other investors, including Jho Low, a Malaysian financier. Federal prosecutors later alleged that Mr. Low had used stolen Malaysian state funds to acquire his 85 percent stake, and the Justice Department moved to seize his interest in the property. In October 2017, with the federal case clouding the hotel’s future, Mr. Witkoff tried to sell the property for $1 billion. No bidders came close.

But the Witkoff Group was on the hook for repaying the loan — a daunting prospect since the odds of selling the hotel at a profit appeared dim.

“We knew he needed the money,” Mr. Allaham said in an interview. He contacted a real estate lawyer whom they both knew and arranged for a sit-down. “It was an easy meeting to get.”

In late 2017 in a suite at the St. Regis, Steve Witkoff and Alex, who was being groomed to take over the family business, met with an entourage of Qataris led by Sheikh Mohammed bin Hamad al-Thani, brother of the emir.

The men discussed the Park Lane and Mr. Trump. Steve Witkoff “described the president and described his long relationship with him,” recalled Mr. Allaham, who also attended the meeting. He said Mr. Witkoff made it clear that he had direct access to Mr. Trump. “We needed access to his friends,” Mr. Allaham said.

Mr. Allaham would quit his work with the Qataris less than a year later, after an acrimonious dispute, and he is now openly critical of the government. (Ms. Kelly, the White House spokeswoman, sought to discredit him by noting that he has donated to Democrats and that his restaurant business faces tax liens.) But for months, he was a central player in Qatar’s influence-building efforts.

In early 2018, Mr. Allaham sat in on another meeting, this one at the Qatar Investment Authority’s Manhattan headquarters. He said Mr. al-Thani proposed investing in real estate projects owned by Mr. Trump’s friends as a way to win favor with the administration. They discussed investing in projects via Apollo, the private-equity firm. The Qatari Investment Authority was the third-largest shareholder in Apollo’s publicly traded real estate financing trust.

Major real estate deals can take years to come together, and Qatar’s first known investment with the Witkoff Group didn’t take place until 2022, after Mr. Trump had left office but while he was eyeing a political comeback. That year, the Apollo trust partnered with the Witkoff Group in developing The Brook, a luxury Brooklyn rental building that opened its doors this summer.

Another deal soon followed. Steve Witkoff was still looking to get out of his investment in the Park Lane Hotel, which had become an albatross. In 2019, he and the building’s co-owner — Abu Dhabi’s sovereign wealth fund, Mubadala — had borrowed hundreds of millions of dollars more to upgrade the building. That brought their total debt on the Park Lane to $615 million. In 2023, the year before those loans came due, the Qatar Investment Authority agreed to buy the Park Lane for $623 million. (Apollo lent Qatar much of the money for the acquisition.) That allowed Mr. Witkoff to escape financially unscathed.

Ms. Dunn, the spokeswoman for the Qatar Investment Authority, said the fund had dealt with Mubadala, not the Witkoffs, when it negotiated the deal.

Early in 2024, the prime minister of Qatar, Sheikh Mohammed bin Abdulrahman Al-Thani flew to Florida to attend Alex Witkoff’s wedding at the Breakers Palm Beach Resort.

Shortly after Mr. Trump was re-elected president, the prime minister sat down with Steve Witkoff in a much more somber setting. He served as lead negotiator for Qatar as Mr. Witkoff and other diplomats gathered in Doha and Paris to discuss a potential cease-fire between Israel and Hamas in Gaza.

In May, while those negotiations were ongoing, the Witkoff Group — run by Alex Witkoff since his father became Middle East envoy — accepted another $100 million from the same Qatar-backed Apollo trust, this time for the Belgrove, a Palm Beach property.

There is no evidence that Qatar’s business relationship with the Witkoff family has affected Steve Witkoff’s diplomatic negotiations. In response to questions from The Times, Ms. Dunn said the Qatar Investment Authority “was not invested in the Brook or Belgrove” but did not answer questions about the investments being made via the Apollo trust.

Joanna Rose, a spokeswoman for Apollo, said investors like Qatar in the company’s real estate trust “have no role in directing or choosing the investments” the trust makes. She noted that investments in Witkoff properties represented a small percentage of the trust’s overall deals.

‘Good, Decent People’

By this spring, Alex Witkoff was in sales mode. He approached Qatar and other major investors, asking them to put money into his planned multibillion-dollar fund. In meetings and in a fund-raising document reviewed by The Times, Alex Witkoff said the so-called Special Situations Real Estate Credit Fund would focus on investments in the Sun Belt and other regions with a shortage of affordable housing.

The fund-raising document said the Witkoff Group hoped to raise $4 billion. Under standard industry fee structures, the manager of a $4 billion real estate fund would likely collect fees of about $80 million annually, or roughly $400 million over the fund’s anticipated five-year life — in addition to a cut of any profits.

The extent of Alex Witkoff’s discussions with various Gulf investors is unclear. A spokesman for the U.A.E. declined to comment, and Kuwaiti representatives didn’t respond to requests for comment. Ms. Dunn said Alex Witkoff had initially approached the Qatar Investment Authority in 2024 and “we communicated our decision not to proceed several months ago.”

As recently as August, however, Alex Witkoff told prospective investors that he had lined up funding pledges from the three countries, according to the people familiar with those pitches.

Some of the same Middle Eastern governments previously did deals with people connected to the Trump administration. In 2022, for example, Qatar and the U.A.E. each invested about $200 million in a firm run by Jared Kushner, Mr. Trump’s son-in-law. (Saudi Arabia kicked in another $2 billion.) But those investments came after Mr. Kushner no longer had a government job.

Ms. LaPorte, the Witkoff Group spokeswoman, said in a statement that the company had decided not to pursue the investment fund solely for economic reasons, including doubts about its prospects for profitability.

She added that Steve Witkoff “has had no involvement in our company since 2024, and so despite the dishonest innuendo, the suggestion that any sort of ‘conflict of interest’ exists is categorically false.”

Since Mr. Trump’s re-election, Zach Witkoff has used cryptocurrency conferences in Dubai and Abu Dhabi as venues to raise billions of dollars from government-linked investors in the United Arab Emirates and elsewhere for World Liberty Financial, the Trump-Witkoff cryptocurrency company.

Yet it is the Qataris with whom Steve Witkoff appears especially close. When Israel agreed to a cease-fire in Gaza early this year, the Qataris, who were central to mediating the negotiations, credited him. Along with Mr. Trump, Mr. Witkoff got the deal “across the line,” said Majed al-Ansari, an adviser to the Qatari prime minister.

In an interview with Tucker Carlson in March, Steve Witkoff said the Qataris were “good, decent people,” whose sole goal was to serve as a peacemaker in the Middle East. “There’s no doubt that they’re an ally of the United States.”

Jesse Drucker, Mike McIntire, Maureen Farrell and Rebecca R. Ruiz contributed reporting. Julie Tate contributed research.