The Trump family's flagship crypto venture, World Liberty Financial (WLFI), has come under intense scrutiny over a $750 million transaction after The Wall Street Journal revealed that Trump-backed entities sit on both sides of the deal. WLFI took over the Nasdaq-listed payments firm Alt5 Sigma, which subsequently raised $750 million from outside investors and used the funds to purchase WLFI's newly created cryptocurrency directly.
The structure could deliver the Trump family an estimated $500 million, as an entity they control retains up to three-quarters of revenues from WLFI token sales. Such circular transactions, where the same party effectively acts as both buyer and seller, are relatively common in crypto markets but rare in traditional finance and typically raise red flags. Howard Fischer, former senior trial counsel at the SEC, told the WSJ that this represents strange and uncharted territory in the securities world, while Corey Frayer, a former SEC official who oversaw crypto policy, warned the deal brings the worst practices of the crypto ecosystem into regulated public markets. Public filings show President Donald Trump personally holds two-thirds of WLFI tokens, with the family's total stake valued at over $6 billion on paper. Alt5 Sigma paid 20 cents per WLFI token, a 50% premium to the price in a recent private sale. Among the backers in the $750 million raise were Steve Cohen's Point72 Asset Management and Hong Kong-based Soul Ventures. Alt5 Sigma, whose predecessor JanOne settled SEC fraud allegations by paying a fine without admitting or denying charges, is pursuing a treasury strategy modelled after MicroStrategy's Bitcoin purchases, but is buying tokens directly from WLFI, a related party that also controls supply.
The WLFI token began trading on 1 September 2025, and crypto has now overtaken real estate as the Trump family's dominant business interest, while the White House rejected criticism through press secretary Karoline Leavitt's statement that neither the president nor his family have ever engaged or will ever engage in conflicts of interest.
Sources:
- https://www.wsj.com/finance/currencies/trump-family-crypto-investments-90e48c87
- https://timesofindia.indiatimes.com/business/international-business/donald-trumps-750-million-crypto-deal-sparks-scrutiny-family-firm-sells-to-itself-cashes-in-big-why-watchdogs-see-red-flags/articleshow/123616920.cms
- https://www.mitrade.com/insights/news/cryptocurrencies/trump-familys-750-million-crypto-deal
