AI Financial Stock Sinks 93% After Trump Family’s $500M Crypto Payday

AI Financial Corp is selling its only profitable business for as little as $15 million, less than a year after a $1.5 billion crypto bet gutted its stock. That bet involved World Liberty Financial, the crypto venture co-founded by Eric Trump and Donald Trump Jr., and it left the shell company’s shares down 93% while the Trump family collected roughly $500 million.

Five Senate Democrats renewed calls on Friday for hearings into the president’s crypto income, hours after new financial disclosures showed his family’s crypto ventures generated close to $1.4 billion in a single year. The company at the center of the original deal, once called Alt5 Sigma, is now fighting to stay listed on the Nasdaq.

A $1.5 Billion Bet Leaves AI Financial Down 93%

The deal closed in August 2025. Alt5 Sigma Corporation, then a small fintech company, agreed to close a $1.5 billion registered offering and private placement built around World Liberty Financial’s token, WLFI. Half the money came in as WLFI tokens, priced at 20 cents each by World Liberty Financial itself, before the token ever traded on a public exchange. Alt5 raised the other half by selling stock to institutional investors, then used that cash to buy still more tokens.

The result was a treasury of 7.28 billion WLFI tokens, once worth more than $1.3 billion. Zach Witkoff, World Liberty Financial’s co-founder and chief executive, became Alt5’s board chairman. Eric Trump was lined up for a board seat before Nasdaq pushed back, and he ended up as a non-voting observer instead.

Shares closed at $8.97 on Aug. 8, 2025, the last trading day before the deal was announced. By early June 2026, the stock, renamed AI Financial Corp and trading under the ticker AIFC, had fallen to around 65 cents, a 93% drop. The WLFI tokens themselves were down roughly 70% from what the company paid for them, according to CoinGecko’s tracker, which shows the position now carrying an unrealized loss of more than $900 million against the original $1.31 billion cost basis.

Now It Is Selling Its Best Business for $15 Million

AI Financial’s fintech subsidiary, Alt5 Sigma Canada, is the part of the company that actually makes money processing crypto payments. On July 7, the Tokyo-based trading firm Perpetuals.com filed paperwork saying it had signed a non-binding term sheet to buy that unit for up to $15 million, according to the Wall Street Journal’s reporting on the talks.

Perpetuals.com builds AI-driven trading products and prediction markets, and the acquisition would reportedly fit that roadmap. Nothing is final. The term sheet is non-binding, and any deal still needs pricing, due diligence and board sign-off on both sides.

What stands out is the scale. A company that raised $1.5 billion to buy crypto tokens eleven months ago is now negotiating to give up its one working, revenue-generating business for a fraction of one percent of that original raise.

Who Actually Walked Away With the Money

Ordinary shareholders who bought AI Financial stock on the open market got hammered. World Liberty Financial and its affiliates did not take the same risk. The deal was structured to give WLFI’s own leadership control of the board and financial protections that retail buyers never had.

• Board control – Zach Witkoff took the chairman’s seat while Zak Folkman, another World Liberty Financial co-founder, joined as a board observer with access to internal documents.
• Warrants and shares – World Liberty Financial received 1 million common shares plus prefunded warrants for 99 million more shares and warrants for another 20 million shares, exercisable between $7.50 and $9.75 apiece, a stake now worth roughly 46% of the company’s fully diluted equity.
• A related-party loan – In January 2026, AI Financial borrowed $15 million from World Liberty Financial itself through a secured, non-recourse loan, then used part of the proceeds trying to prop up its own falling share price. The effort failed.
• Price-setting power – World Liberty Financial set the 20-cent token price used in the deal before WLFI ever traded publicly, meaning outside shareholders had no market reference point to judge whether the price was fair.

Company filings also show AI Financial has burned through leadership. It is now on its third chief executive and third outside auditor since the deal closed, after suspending former CEO Peter Tassiopoulos and cycling through auditors so quickly that one hire lasted barely over two weeks before being dismissed. Eric Trump’s name was quietly removed from the company’s leadership page in late April, and he wrote on social platform X in May that he has “zero leadership or decision-making role in the company.”

Senate Democrats Want Hearings, Again

The pressure escalated again on Friday. Senators Elizabeth Warren of Massachusetts, Richard Blumenthal, Gary Peters, Dick Durbin and Ron Wyden sent a letter demanding hearings into President Trump’s crypto holdings, pointing to a new financial disclosure showing more than $580 million in crypto-related income last year, including about $515 million from WLFI token sales. Trump also reported $635 million in royalties tied to his memecoin business, for total crypto-linked income the senators put near $1.4 billion for the year. Oton Technology has previously covered how that $1.4 billion disclosure broke down line by line.

Their letter also flagged a reported 49% stake in World Liberty Financial held by a group linked to Sheikh Tahnoon bin Zayed Al Nahyan, the United Arab Emirates’ national security adviser, questioning whether foreign money is buying access to U.S. policy. Republicans control the committees that would need to schedule any hearing, and they have not done so in response to this or earlier Democratic requests.

Trump defended the ventures in a CNBC interview at the White House last week, saying there was nothing illegal about them. “I tell my kids, stay away from as much as you can stay away from, but they also have a life,” he said, adding that Eric Trump oversees his assets and outside firms manage his investments. The White House has said Trump’s assets sit in a trust managed by his children and that no conflicts exist.

None of this is new pressure exactly, it is compounding pressure. A nonpartisan watchdog, the Democracy Defenders Fund, sent the Securities and Exchange Commission a letter in April arguing the regulator needed to open an investigation into AI Financial “without delay.” It never received a response.

The question now is: What happened to all that money?

Virginia Canter, the Democracy Defenders Fund’s chief anti-corruption counsel, posed that question in an interview about the deal. Matthew Platkin, New Jersey’s former attorney general, reviewed the Alt5 episode separately and reached a similar conclusion, saying the company had “all the indicators that normally raise significant concerns among regulators.”

What We Know

• World Liberty Financial disclosures show the Trump family was entitled to roughly $500 million from the 2025 token transaction.
• Five Senate Democrats formally asked for hearings on July 10, citing the new $1.4 billion income disclosure.
• The Democracy Defenders Fund’s April letter to the SEC asking for a probe went unanswered.
• The White House maintains Trump’s assets are held in a trust with no conflicts of interest.

What’s Unconfirmed

• Whether the SEC has opened any actual investigation into AI Financial or World Liberty Financial.
• Whether AI Financial avoided Nasdaq delisting after its share-price compliance window closed.
• The precise final size of the Trump family’s take, since estimates have grown from an initial $412.5 million figure reported in August 2025 to roughly $500 million more recently.

Trump’s Other Crypto Bets Followed the Same Script

AI Financial is not an isolated case. Other Trump-linked crypto assets have lost significant value since launch, including a bitcoin mining stock and the president’s own memecoin, which has been steadily losing value since its debut. A financial analysis of the pattern put it plainly.

In each of these ventures, the Trumps licensed the family name, promoted the projects publicly, and collected revenue as investors piled in; when prices collapsed, the family stayed profitable while the investors absorbed the losses.

World Liberty Financial itself has drawn scrutiny well beyond the AI Financial deal. Crypto figure Justin Sun, an early WLFI investor, sued the company in April alleging it froze tokens worth up to $1 billion after he declined to invest further in its stablecoin project. World Liberty Financial has also faced questions from lawmakers over token sales to entities with alleged ties to North Korea and Russia, and over a 49% stake reportedly sold to UAE-linked investors months before the Trump administration approved advanced chip exports to the UAE.

Is AI Financial About to Get Delisted?

AI Financial’s Nasdaq listing depends on its stock price, and as of early June the company had a narrow window to fix it. Nasdaq told the company it had 15 trading days to lift its share price out of penny-stock territory or face delisting proceedings, a deadline that has since run its course without a confirmed public resolution.

The stock’s arc captures how far the company has fallen. Shares once closed as high as $10.26 in mid-2025, months before WLFI ever entered the picture, according to Macrotrends’ historical pricing data. The table below tracks the slide since the deal itself was announced.

Company filings in June said the going-concern risk had been “substantially mitigated” and that it had enough liquidity for the next 12 months. That statement addressed cash flow, not the separate Nasdaq price requirement, and the two problems remain distinct. The Perpetuals.com talks over Alt5 Sigma Canada are still non-binding, with due diligence ongoing on both sides.

Frequently Asked Questions

What Is AI Financial Corp, and Why Was It Called Alt5 Sigma?

AI Financial Corp is the same public company that traded as Alt5 Sigma until an April 2026 rebrand and ticker change to AIFC. Before settling into crypto payments in 2024, the shell company had passed through a recycling business and a biotech division; it still owns a spinoff called Alyea Therapeutics, which holds an FDA Orphan Drug Designation for a pain treatment called JAN123.

How Much Did the Trump Family Actually Make From the Deal?

World Liberty Financial disclosures point to roughly $500 million, though an August 2025 New Yorker analysis had estimated the figure at $412.5 million before more proceeds came in. Public disclosures also show that 75% of WLFI token sale proceeds route to DT Marks DEFI LLC, an entity controlled by the Trump family.

Can AI Financial Sell Its WLFI Tokens To Raise Cash?

No, not yet. The 7.28 billion tokens remain locked under the original purchase agreements. About 3.2 billion of them can be pledged as loan collateral, which is how the company arranged its $15 million related-party loan from World Liberty Financial in January 2026.

Is the SEC Investigating World Liberty Financial or AI Financial?

There is no confirmed investigation as of this writing. The Securities and Exchange Commission has declined to comment on whether it has looked at AI Financial specifically, and it never responded to the Democracy Defenders Fund’s April letter requesting a probe.

What Happens if Nasdaq Delists AI Financial’s Stock?

A delisting would push shares onto over-the-counter markets, where trading volume typically thins out and many institutional funds are barred from holding the stock. Companies facing this outcome often attempt a reverse stock split to lift the per-share price back above Nasdaq’s minimum before a final delisting notice takes effect.

Disclaimer: This article is for informational purposes only and does not constitute investment, legal or financial advice. Cryptocurrency and penny-stock investments carry substantial risk, including total loss of principal. Consult a licensed financial professional before making investment decisions. Figures cited are accurate as of the July 10, 2026 publication date and are drawn from company filings and the news reports linked above.