An obscure financial entity with connections to a Caribbean-island bank that bills itself as a top payment service for adult entertainment sites would gain a sizable stake in former president Donald Trump’s media company if its merger deal proceeds, according to internal documents a company whistleblower has shared with federal investigators and the Washington Post.
Yet the role ES Family Trust would assume in Trump Media and Technology Group has never been officially disclosed to the Securities and Exchange Commission or to shareholders in Digital World Acquisition, the special purpose acquisition company, or SPAC, that has proposed merging with Trump’s company.
The companies also have not disclosed to shareholders or the SEC that Trump Media paid a $240,000 finder’s fee for helping to arrange the $8 million loan deal with ES Family Trust — or that the recipient of that fee was an outside brokerage associated with Patrick Orlando, then Digital World’s CEO.
Where ES Family Trust obtained the money, and who is behind the trust, remain publicly unknown, omissions that unnerved some of Trump Media’s top executives when they first learned of the loan in late 2021, according to Will Wilkerson, a whistleblower who at the time was the company’s executive vice president of operations.
Republican members of Congress and Trump supporters have complained for months that the SEC’s year-long delay in approving the merger has been fueled by anti-Trump bias and a “woke political agenda.” Trump Media’s primary business is the social media site Truth Social.
But the financial tangle offers a possible explanation for why the SEC has yet to approve the deal, said Michael Ohlrogge, a New York University law professor who studies SPACs. He called the deal unusual and rife with questionable decisions and potential conflicts of interest.
“This is definitely something that could cause problems,” he said. “At a minimum, if the SEC knew about this loan, it would insist that it be disclosed to [Digital World] shareholders. … And the company didn’t even do that.”
Representatives for Trump Media and Digital World did not respond to requests for comment for this story.
In a statement last month, a Trump Media spokeswoman said a Post report then on the company was based on “discredited hit pieces, defamatory allegations and false statistics” but did not dispute any specific claims. Digital World’s interim chief, Eric Swider, who assumed the role in March, said in emails last month that the Post report included “inaccuracies” but did not say what they were.
Messages sent to ES Family Trust’s only known trustee and an associated email account yielded no response. A person who answered a phone number listed for the bank that transmitted the loan, Paxum Bank, said the company declined to comment. Representatives for the bank’s owner, Anton Postolnikov, did not respond to requests for comment.
A spokesman for Trump’s 2024 campaign declined to comment.
A lifeline appears
Digital World has faced a troubled path since pledging to merge with Trump Media in October 2021, an announcement that sparked a massive trading frenzy. Almost immediately, the company faced suspicions that Digital World had held merger talks with Trump Media before going public, a possible violation of SEC rules.
Digital World told investors last month that it was cooperating with investigators from the SEC, Justice Department and Financial Industry Regulatory Authority (Finra) but did not provide details on what was being examined. The federal agencies and Finra, an industry group, declined to provide more detail.
The ongoing investigation has halted Digital World’s ability to merge with Trump Media and unlock more than $1 billion in investor funds. Digital World’s board fired Orlando as chairman and chief executive in March, saying in an SEC filing that the company was facing “unprecedented headwinds” and that his “departure enables the Board to appoint new leadership, which it believes will restore confidence to the shareholders.” Orlando did not respond to requests for comment.
In a separate SEC filing last month, the company said that, by the end of last year, it had just $989 in cash on hand and more than $17 million in debts. Most SPACs don’t rack up anything close to this level of debt, Ohlrogge said, because “the normal costs of running a SPAC, finding a target and negotiating with that target are not very expensive.”
In late 2021, the frozen merger was also raising concerns inside Trump Media over its ability to pay the bills, Wilkerson recalled. Then, he said, Orlando revealed he had made a breakthrough: a loan deal worth up to $8 million from an entity called ES Family Trust.
In a convertible promissory note dated Dec. 23, 2021, Trump Media was offered the money in exchange for agreeing to “automatically” convert the loan principal into “shares of Company Stock” once the merger with Digital World occurred, according to a copy of the document reviewed by the Post. The document does not say precisely how much stock ES Family Trust would receive. Trump estimated last month that the company, of which he owns 90 percent, is worth between $5 million and $25 million.
The document included blanks for signatures from Wilkerson’s fellow co-founders at Trump Media, Wes Moss and Andy Litinsky, as well as Angel Pacheco, the trust’s only named trustee.
Moss signed it, according to a copy reviewed by the Post, but Litinsky declined after expressing concerns that the company hadn’t undertaken enough due diligence on where the money had come from, Wilkerson said. Litinsky and Moss did not respond to requests for comment. Both men were on the company’s board at the time but left last year amid a company shake-up.
Pacheco also did not sign the document, a copy shows, and Wilkerson’s attorneys have not found a more updated document in a trove of 150,000 records they’ve shared with investigators. The money was sent anyway.
A wire transfer document dated that same day shows that $2 million was sent to Trump Media by Paxum Bank, whose main office is on the small Caribbean island of Dominica. A separate wire transfer document, dated Feb. 17, 2022, shows Trump Media being paid another $6 million by ES Family Trust.
No names, addresses or details are listed for ES Family Trust except for Pacheco’s name. Pacheco’s LinkedIn account says he has been a director at Paxum Bank Limited since 2019 and has “international payment expertise.” Pacheco did not respond to requests for comment.
In January 2022, Trump Media agreed to pay a cash referral fee — equal to 3 percent of the $8 million loans, or $240,000 — to a Houston-based brokerage firm called Entoro Securities, according to a referral fee agreement and an Entoro invoice provided by Wilkerson.
The referral fee agreement names “Anton Postolnikov and affiliated entities” as “Introduced Parties” who participated in the deal. Orlando is a registered broker at Entoro, according to a database run by Finra, and Orlando’s LinkedIn profile says he has been a managing director there since 2020.
Unease over the money
Questions around the sudden influx of cash fueled unease inside the company for months, Wilkerson said, but the executives ultimately decided against giving it back, deeming it too critical to keeping the business afloat.
It’s unclear how closely anyone inside Trump Media looked into ES Family Trust or Paxum at the time of the loans.
An attorney working with Trump Media, John Haley, sent a brief email about the first $2 million in December 2021 to Donald Trump Jr., before the former president’s son joined the company’s board, saying there was “no guaranty that these will get signed and funded, but we remain hopeful,” according to a copy of the correspondence shared by Wilkerson.
Trump Jr. responded, “Thanks John much appreciated. d,” the email shows. Trump Jr. and Haley did not respond to requests for comment.
A month after the second payment, Trump Media executives still knew little about the origin of the money. On March 8, 2022, the company’s chief financial officer, Phillip Juhan, sent an email to the then-chief legal officer of another Orlando-run firm, Benessere Investment Group, seeking contact information for anyone at ES Family Trust.
The information, Juhan wrote, was needed by the company’s outside auditors, BF Borgers, which required a confirmation statement from all noteholders who had lent Trump Media money. Trump Media had only Pacheco’s name, Juhan wrote.
The response from the Benessere executive, Alexander Monje, was a single sentence: “Hey Philip, it is [email protected],” with no other names or addresses attached, according to a copy of the exchange shared by Wilkerson. Proton Mail is an encrypted email service based in Switzerland.
Juhan, Monje and BF Borgers did not respond to requests for comment. Emails sent to the Proton Mail address yielded no response.
Digital World did not tell investors about the $8 million in loans or Entoro’s referral fee in its filings submitted to the SEC, a review of public documents shows. Ohlrogge said the SEC could insist the loans should have been disclosed to investors, given that the concerns over its origins and Orlando’s finder’s fee could affect the value of the shares.
“The right way for him to have done this is to say: ‘I know this transaction looks potentially bad and may be enriching me at the expense of [Digital World] shareholders, but I really think it’s ultimately in their best interest,'” Ohlrogge said. “That’s the right way to do it. And he didn’t do anything of the sort.”
‘#1 trusted … for the adult industry’
The Post has been unable to find any registration documents for ES Family Trust. ES Family Trust has made no public statement.
Postolnikov, whose name appeared on the referral-fee document, is an owner of Paxum Bank and employs Pacheco, ES Family Trust’s named trustee. Postolnikov said in a 2018 federal court filing that he is “the principal of Paxum Bank,” and a company statement in March called him its “primary owner.”
Paxum itself remains a mystery. The company has promoted itself online as a way for video streamers of adult content to coordinate financial transactions across international borders and, in 2021, Paxum’s then-chief executive, Andrei Octav Moise, told BCAMS Magazine, a trade publication for the business of live webcam models, that the bank was “proud and happy to be considered the #1 trusted payment service for the adult industry!”
On Thursday, Moise insisted that he wasn’t familiar with Paxum’s activities or the Trump Media transaction and said he “never had any job or [ownership] or any control” in the bank. On Friday, the adult-industry trade publications AVN and Xbiz reported that Moise had decided to push for a sale of Paxum and would be “retiring” from the industry. He was quoted as saying, “It has been both a privilege and a pleasure to lead the development of Paxum into one of the premier global payment platforms.”
Before Paxum, Postolnikov worked as an entrepreneur in Russia, running a now-defunct online car-rental company in St. Petersburg, according to PitchBook, a corporate database. In 2016, he bought Dek-Co, a London-based payments firm, according to his online profile. In British business filings last year, Dek-Co said he is “the shareholder” of Paxum and Dek-Co’s chief executive and “ultimate controlling party.”
It’s unclear when Postolnikov moved to the United States. In the past two years, he has invested millions of dollars in luxury real estate on Fisher Island, a private enclave off the coast of Miami Beach that Bloomberg in 2020 named “America’s richest Zip code.” Miami-Dade property records show that a company he owns bought two waterfront condos: one for $6 million in April 2021 and another for $7 million in December 2021.
Postolnikov, in March 2021, also gave $30,000 to the reelection campaign of Florida Gov. Ron DeSantis (R), according to a contribution list published last year by the political committee Friends of Ron DeSantis.
DeSantis representatives did not respond to an email asking whether DeSantis and Postolnikov had a personal or business relationship. The governor filed a notice this week that he is no longer associated with the committee, a standard move due to his expected shift toward a presidential primary campaign in which he would compete against Trump.
Postolnikov is the nephew of Alexander Smirnov, a former deputy justice minister in the Russian government, according to a 2016 report by Delovoy Peterburg, a Russian business newspaper. Smirnov became general director of the state-controlled maritime company Rosmorport in 2021, according to published reports.
Postolnikov and his aunt, Smirnov’s wife, Elena Smirnova, previously worked together at Russia’s United Bureau of Credit History, according to Delovoy Peterburg. There is no evidence that Smirnov or Smirnova are involved in the Trump Media deal.
The Guardian reported in March that federal prosecutors in New York have been investigating whether the Trump Media loans violated money-laundering statutes, which mandate that companies and investment advisers take steps to learn basic information about their lenders and clients.
After the Guardian’s report, an online news outlet in Dominica called Nature Isle News published a response attributed to an unnamed firm representing Paxum and Postolnikov. That response said Postolnikov was a U.S. citizen and had for two years “been the subject of false media smears that have originated in Russia, all to blackmail Anton into paying bitcoin to remove the stories from the internet.”
The statement denied that Paxum and Postolnikov are “in any manner involved in ‘money laundering’ or loaning out Russian funds” and said that Paxum’s compliance department ensures all transactions adhere to money-laundering rules.
Trump Media’s chief executive, the former Republican congressman Devin Nunes, said in a lawsuit after the Guardian report that “the entire story is fabricated” and that neither he nor the company’s leaders had been involved in the transaction. Nunes did not respond to requests for comment.
Carlisle Jno Baptiste, the Nature Isle News’ managing editor, said a Paxum lawyer sent him the response after he asked the company for comment on the Guardian’s report. Baptiste said Paxum has an office in the center of Roseau, the island’s capital, but that it had rarely been a topic of local conversation before the money-laundering claims arose.
“There’s a lot of talk about that now,” he said.
‘Basically my life savings’
Company-SPAC mergers are traditionally quick and straightforward affairs, according to a 2020 presentation by lawyers at the firm Morgan Lewis. A SPAC submits a merger registration document called an S-4; the SEC reviews it and asks further questions, often within 30 days; the company sends in answers in an amended filing, the SEC responds within 14 days, and the whole process generally wraps up within a matter of months.
Digital World’s S-4, however, has been in limbo since May 16, 2022, SEC records show. The most recent correspondence from the SEC to Digital World, in August, was a terse boilerplate letter in which an agency official said, “We remind you that the company and its management are responsible for the accuracy and adequacy of their disclosures,” public SEC records show.
That delay has become the focus of Trump Media CEO Nunes and other Trump allies, who argue that biased regulators at the SEC have delayed the merger in hopes of suffocating Trump’s company and fueling a political witch hunt.
“The SEC and [SEC Chair Gary] Gensler have been holding this up. The guy clearly has a grudge against us, against Trump,” Nunes said last month on the right-wing news channel Newsmax. “This is a major scandal that’s brewing at the SEC: their willingness to play politics and discriminate against people who like our little company, our start-up company … [and] are being wiped out.”
At a House Financial Services Committee hearing last month, Gensler told Republicans who were grilling him about the delay that SEC officials were working to make sure all merger filings “are accurate and in compliance with the law.”
But Republicans weren’t calmed. The SEC is “focused on a woke political agenda rather than focused on their job,” Rep. Bryan Steil (R-Wis.), chair of the House Administration Committee, which oversees House management matters and U.S. Capitol security, said in a recent interview with John Solomon of the conservative media outlet Just the News.
Rep. Dan Meuser (R-Pa.) wrote last week in the Washington Examiner, another conservative outlet, that the delay was hurting “blue-collar people,” including “the millions of conservative investors who have put their hard-earned money into this project.”
Neither Steil nor Meuser responded to a request for comment from the Post.
Tom Sas, the 40-year-old founder of a cloud-computing start-up in Chicago who says he twice voted for Trump for president, counts himself among the injured.
In October 2021, when Digital World’s merger announcement sparked a stock-market frenzy, Sas bought nearly 1,200 shares at $70. Then, while listening to investing YouTubers predict that the stock could go to $300, he said, he felt a deep fear of missing out, saying, “FOMO hit me hard.”
He entered a market order to buy thousands more shares, expecting he would get them at $90, but the stock’s volatility led to a halt in trading. When the stock came back online, he said, his order was unexpectedly filled at the stock’s all-time high, $175 a share, draining his entire account.
All in all, he spent more than $516,000 in cash on Digital World shares, according to investment account documentation he provided. “This was basically my life savings,” he said, adding that he doesn’t own any property and drives a 2011 Ford Fiesta. Digital World shares now trade for about $13.
Sas said he was initially excited about the prospect of Truth Social being a “true, non-biased news outlet” and that he hopes “the people running Trump Media, if they see some things not going right, they get in there and fix it.”
He echoed other supporters of Digital World and Trump in blaming a “biased” SEC for stalling the merger. “I’m left holding the bag now, hoping something goes through and it doesn’t collapse,” he said.
The Washington Post’s Magda Jean-Louis contributed to this report.
