Trump’s Media Company Is Investigated Over Financing Deal

One day in April, a group of men gathered on a videoconference call to discuss a deal to bankroll former President Donald J. Trump’s planned media company.

Among the participants, according to two people familiar with the call, were Mr. Trump’s representatives and the chief executive and a future board member of Digital World Acquisition, a so-called blank-check company that would announce the deal with Mr. Trump six months later.

At the time, Patrick Orlando, Digital World’s chief executive, was also running several other blank-check companies, and it’s unclear which one he was representing on the videoconference.

Yet the month after the video call, which has not been previously reported, Digital World said in securities filings that it had not identified or begun talking with any potential merger targets.

Blank-check companies like Digital World, also called special purpose acquisition companies, or SPACs, sell their shares to investors first and then go looking for a business to merge with. They aren’t supposed to have a deal lined up before selling shares.

On Monday, Digital World said regulators were investigating. The Securities and Exchange Commission has requested information about the deal, including the identities of some investors and “certain documents and communications” between the SPAC and Mr. Trump’s company, Trump Media & Technology Group.

“The investigation does not mean that the S.E.C. has concluded that anyone violated the law,” Digital World said in its filing.

Also on Monday, Trump Media announced that Representative Devin Nunes, Republican of California, was retiring from Congress to become chief executive of the company.

If regulators find that Digital World’s filings included false or misleading statements, they could take action against the company or its backers — potentially complicating the planned merger. Hundreds of millions of dollars are at stake for Mr. Trump’s company: Last week, Trump Media announced that unidentified investors had agreed to plow $1 billion into the company — on top of the nearly $300 million that Digital World raised in its September initial public offering.

The New York Times reported in October that Trump Media’s discussion of a deal with an executive of Digital World may have skirted securities laws because the SPAC did not disclose those talks in its filings. The April videoconference is a further indication that may have happened.

“The S.E.C. requires disclosure of deals that may be in the works so everyone is working with the same information,” said Tyler Gellasch, a former S.E.C. lawyer who is a fellow at Duke University School of Law.

In addition to Mr. Orlando, the chief executive of Digital World, the video call included Andy Litinsky and Wes Moss, two former contestants on “The Apprentice” who had pitched the Trump social media venture to the former president shortly after he left office in January.

Lori Heyer-Bednar, the chief legal officer for Trump Media, said the videoconference was “strictly discussions between” Trump Media and Benessere Capital Acquisition, another SPAC that Mr. Orlando ran. “Any reference to the contrary is false and defamatory,” Ms. Heyer-Bednar said. She added that more information about how the deal had come together would be included in a future securities filing.

Another participant on the videoconference was Rodrigo Veloso, who in July was named one of Digital World’s independent board members. Mr. Veloso, the founder of a company that made O.N.E. coconut water and a friend of Mr. Orlando’s, participated on the call as an adviser to Mr. Orlando, according to a person familiar with the matter.

In a brief interview, Mr. Veloso said he had “no recollection” of the April meeting.

As it looks into the Trump SPAC, the Securities and Exchange Commission will most likely encounter ARC Group, a Shanghai financier that the agency has reprimanded in the past. In 2017, the S.E.C. stopped ARC’s executives from listing shares of three companies, citing “material misstatements” in their securities filings and a lack of cooperation from the executives.

ARC is also a main backer of Digital World and a key architect of the SPAC deal with Trump Media. (There is no indication that the S.E.C. is investigating ARC for its role in the Trump deal.) Founded six years ago by Abraham Cinta, who was raised in Mexico but lived in Shanghai, ARC has tried its hand at several businesses. It initially tried to start a Spanish wine and olive oil import business in Asia, then pivoted to helping Chinese companies list their shares on American stock exchanges.

More recently, when Wall Street became infatuated with SPACs — a kind of company that had been around for decades but rarely grabbed headlines — ARC shifted its focus again, building a business providing them with seed money and advice.

But in its efforts to project an image of success, the firm at times cut corners. Some ARC executives complained to leaders about the firm’s sloppiness with paperwork and its penchant for exaggerating its size, including by overstating its number of global locations, two people with knowledge of the complaints said.

ARC also exaggerated its Wall Street credentials. The company said on its website that it had a strategic partnership with Morgan Stanley. A Morgan Stanley spokeswoman said that there was no such partnership and that the company had asked ARC to remove its name from its website.

An ARC marketing brochure reviewed by The Times listed other “strategic partners,” including JPMorgan Chase, Goldman Sachs Group, the law firm Skadden Arps, and the accounting firms PwC and KPMG. Representatives of those companies all said they had no relationship with ARC.

ARC had tapped Mr. Orlando to be the chief executive of several of its SPACs, including Benessere, which raised $100 million in a stock offering early this year. As recently as March, ARC had been trying to broker a merger between Benessere and Trump Media.

That month, a small investment bank, Kingswood Capital Markets, which has frequently teamed up with ARC, made a presentation to Benessere’s board members. Marked “strictly private and confidential,” the presentation, reviewed by The Times, listed about a half-dozen possible acquisition targets. One was Trump Media. Kingswood, now called EF Hutton, estimated that Trump Media was worth $1.5 billion and that within a few years it could generate $2.3 billion in annual revenue.

Sergio Camarero, a managing partner at ARC, told Benessere officials that Trump Media was their preferred target. Some Benessere officials, however, balked because they didn’t want to have anything to do with Mr. Trump, two people familiar with the discussions said.

Mr. Camarero did not respond to requests for comment.

ARC quickly turned to Digital World, its other SPAC, as a potential vehicle to merge with the Trump company. ARC had recently installed Mr. Orlando as Digital World’s chief executive, after its previous C.E.O. failed to raise enough money to get it off the ground, a person with direct knowledge of the situation said.

The videoconference call involving ARC, Mr. Orlando, Mr. Veloso and members of the Trump team took place in early April. At the time, Digital World had not yet filed with the S.E.C. to sell its shares to the public. It did so seven weeks later, on May 26.

“We have not selected any specific business combination target and we have not, nor has anyone on our behalf, initiated any substantive discussions, directly or indirectly, with any business combination target,” Digital World said in its initial filing.

The disclosure was important. Because regulators allow blank-check companies to sell their shares to the public with minimal financial disclosures, the companies are not allowed to have merger partners in mind before their I.P.O.s. The thinking is that they otherwise would serve as a backdoor channel for companies to go public while escaping rigorous public scrutiny.

By the summer, Digital World’s public offering was taking shape. The company said in July that it hoped to raise nearly $350 million from investors. Around then, The Times previously reported, a Trump Media executive told people that the company was in an “exclusive agreement” to merge with an unidentified SPAC.

Digital World went public on Sept. 8, raising $293 million. Later that month, Trump Media signed a letter of intent with Digital World. On Oct. 20, Mr. Orlando and Mr. Veloso, the board member who took part in the April video call, went to Mar-a-Lago for the official announcement of the deal.

Shares of Digital World surged to $94, from $10, immediately after the merger announcement, although the stock has since given up more than half of those gains. Digital World also disclosed on Monday that the Financial Industry Regulatory Authority had requested information about trading activity before the announcement of the merger.

Days after the merger was unveiled, Mr. Cinta, the ARC chief executive, agreed to participate in an online discussion about the deal, titled “The Deal That Shook Wall Street.”

But in recent weeks, ARC has taken steps to lower its profile. The firm removed a 2020 presentation that listed Mr. Orlando as a “senior adviser” to ARC.

Mr. Cinta’s planned online discussion was also shelved. The sponsor of the event, Voice of ASEAN TV, said in a posting on LinkedIn that it was being canceled “owing to legal and confidentiality issues arising from Securities and Exchange Commission regulations.” It is now tentatively set to occur on Christmas Eve.

Reporting was contributed by Alexandra Stevenson, Cao Li, Lauren Hirsch and Carlotta Gall. Kitty Bennett contributed research.