Trump Media & Technology Group (TMTG), the media company linked to former U.S. President Donald Trump, is making headlines in the world of crypto finance. TMTG has announced plans to purchase over $2.5 billion worth of Bitcoin, positioning itself as one of the largest potential corporate holders of the digital asset. The decision comes just weeks after U.S. regulators closed an investigation into DRW Investments, one of the major players behind the funding.
Chicago-based DRW Investments has taken the lead in this unprecedented move, pouring $100 million into the Trump-linked media group in exchange for 4 million shares. Founded by seasoned trader Don Wilson, DRW has been active in crypto markets for over a decade and treats Bitcoin as a long-term corporate asset. This investment reflects DRW’s continued belief in Bitcoin’s strategic role on corporate balance sheets and marks a significant endorsement of TMTG’s crypto ambitions.
— Jake M. Grumbach (@JakeMGrumbach) June 14, 2025News update from the swamp:
"An American financier invested $100 million in the Trump family’s flagship bitcoin project just nine weeks after a probe into his crypto business was dropped by the Trump administration." pic.twitter.com/ibiLp38CNC
The story gained further traction when Jane Street, a prominent Wall Street trading firm, acquired a $375 million stake in TMTG, making it the single largest investor so far. According to reports, more institutional investors are preparing to follow suit, helping the media company reach its ambitious $2.5 billion fundraising goal. If fully realized, TMTG would acquire roughly 140,000 BTC at current market prices, placing it among the world’s largest Bitcoin-holding corporations.
At the time of writing, Bitcoin is trading at $10,992 with a 24-hour trading volume of $ 48.57B, and a market cap of $ 2.09T. The BTC price increased 0.16% in the last 24 hours.
On Friday, June 13, the U.S. Securities and Exchange Commission (SEC) approved TMTG’s registration statement, allowing the firm to issue 56 million new shares and 29 million in convertible notes. This green light officially authorizes TMTG to begin its capital raise while placing the company under ongoing SEC regulatory oversight. The timing of this approval is critical, aligning closely with TMTG’s active push into crypto finance.
Meanwhile, DRW is also challenging the current U.S. regulatory structure. In a public statement, the firm suggested that agencies such as the SEC and the Commodity Futures Trading Commission (CFTC) are no longer aligned with the pace of global financial innovation. The call for reform reflects a growing frustration within the crypto sector about outdated regulatory frameworks.
Notably, DRW’s crypto subsidiary Cumberland previously acquired 70,000 BTC during a U.S. government auction of Silk Road assets, now valued at around $7.7 billion. This track record adds weight to DRW’s position and underlines its influence within the digital asset market.
TMTG’s massive Bitcoin bet mirrors moves made by companies like MicroStrategy but with added political and media dimensions. If successful, the acquisition could turn TMTG into a major force in the digital asset space, blurring the lines between media, politics, and crypto finance. As institutional interest in Bitcoin grows, Trump Media’s high-stakes gamble could be a defining moment in the evolving relationship between Wall Street and digital currency.
