Trump family’s crypto gains stay largely unaffected by bear markets after two years of rug pulls

It is June 2029, the crypto market is in full-blown winter, yet the Trump family’s crypto money looks far safer than Bitcoin and the stocks tied to one of their biggest crypto-related deals.

Eric Trump and Donald Trump Jr. helped launch a public-market crypto play in August, but less than 10 months later, the company that bought the tokens is warning investors it may not survive, while the Trump family remains tied to roughly $500 million from the sale.

Eric and Don went to the Nasdaq stock exchange in New York to celebrate the partnership with Alt5 Sigma, a small public company that later became AI Financial Corp. (NASDAQ: AIFC), promising to give stock investors a way to bet on a cryptocurrency backed by the Trump family.

But then, Alt5 closed at $8.97 on August 8, right before the deal was announced, and by press time, AIFC had fallen to $0.66, a 93% loss, according to Yahoo Finance data.

AI Financial warns investors while Trump token-sale proceeds stay protected

AI Financial has now told investors it may not be able to keep operating for much longer. The company’s share price has dropped more than 90%, and the name change from Alt5 Sigma to AI Financial has not pulled buyers back in.

If AIFC cannot keep its stock price above penny-stock levels within the next 15 trading days, it could face delisting from Nasdaq, which is operated by Nasdaq Inc. (NASDAQ: NDAQ).

The August deal gave the Trump family’s crypto company, World Liberty Financial, a huge payday. Alt5 bought $1.5 billion worth of WLFI tokens from World Liberty, which Eric, Donald Jr., and others co-founded in 2024.

World Liberty’s own disclosures said Trump and unnamed members of his family were entitled to about $500 million from that token sale after fees and expenses.

The setup was even better for the Trump family because World Liberty’s token documents gave them 75% of the proceeds from token sales. That detail appeared in a 2024 token-offering document and also in small print on World Liberty’s website.

The Trump family also had indirect exposure to AI Financial through World Liberty’s stake in the company. SEC filings said World Liberty received 1 million AI Financial shares, 99 million prefunded warrants, and 20 million additional warrants split across different batches. Those warrants can be exercised between $7.50 and $9.75 per share.

Democracy Defenders Fund, a nonpartisan group that has criticized ethics issues around the Trump administration, pushed the Securities and Exchange Commission to investigate. Its lawyers sent an April letter asking the SEC to “commence an independent investigation into ALTS without delay.” The group said it got no response.

Virginia Canter, the group’s chief anti-corruption counsel, put the question bluntly in an interview: “The question now is: What happened to all that money?”

AIFC loses value as audits, management changes, and WLFI prices add pressure

AI Financial’s problems did not stop at the chart. After the World Liberty deal, the company disclosed that a Rwandan court had found an employee of its Canadian subsidiary guilty of offenses that included money laundering. AI Financial said that the case was under appeal.

Then came the leadership mess. In October, Alt5 said it had suspended its CEO. The acting replacement was removed in November. A third CEO then took over and is still running the company. The company reported those changes in SEC filings without giving more details.

The paperwork problems arrived soon after. In November, Alt5 told investors that Nasdaq had warned it about a possible delisting because it failed to file its quarterly report on time. That same month, its outside auditor resigned.

The company hired another auditor, then said in December it needed a third one after finding out the second auditor’s license had expired. Alt5 later filed the missing report and said that the Nasdaq warning had been resolved.

AI Financial also had an old regulatory issue from before its crypto era. In 2024, when the company was called JanOne and was still in its biotech phase, the SEC settled a fraud allegation with the business. The company paid a $250,000 fine and did not admit wrongdoing.

The crypto side has also been ugly. AI Financial’s main holding is its pile of WLFI tokens. After fees and expenses, the $1.5 billion deal gave the company 7.3 billion WLFI tokens at $0.20 each. By June 8, Coinbase Global Inc. (NASDAQ: COIN) showed WLFI trading around $0.057, down 72%.

That left AI Financial’s WLFI stash worth about $412 million. Its whole market cap, though, was only $89 million, based on FactSet data. That gap suggests traders see AIFC as riskier than simply holding the token directly.

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