US President Donald Trump’s media group is making a big splash in crypto finance. A Chicago trading firm put up $100 million to buy 4 million shares in Trump Media & Technology Group. That move comes just nine weeks after US regulators closed a probe into the same firm. Based on reports, the deal is tied to TMTG’s plan to buy over $2.5 billion worth of Bitcoin. Related Reading: Crypto Bloodbath: Over $1 Billion Liquidated As Iran-Israel Tensions Erupt Big Bet On Trump Coin According to the filing, DRW Investments treats Bitcoin like any other corporate asset. The company – founded and controlled by trading mogul Don Wilson – said it has been active in crypto for more than a decade. It sees value in holding Bitcoin on its balance sheets. Buying into TMTG was, in its view, a straightforward way to back that idea. News 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 — Jake M. Grumbach (@JakeMGrumbach) June 14, 2025 Institutional Backers Rally Jane Street leads the pack with a $375 million stake in the Trump Group. That makes it the largest backer so far. Other investors are also lining up. Based on reports, TMTG’s goal is to raise $2.5 billion and use much of that cash to buy Bitcoin. If all goes to plan, the firm could hold over 140,000 BTC at current prices. Regulatory Milestone Achieved On Friday, June 13, the SEC declared TMTG’s registration statement for its Bitcoin Treasury offering effective. That covers 56 million new shares of equity and 29 million in convertible notes. Clearing this step means the company can sell shares and raise the cash it needs. It also subjects TMTG to ongoing SEC reporting and oversight. Voice Of The Crypto Industry Meanwhile, a DRW spokesperson called for a fresh look at the SEC and CFTC. The firm argued that the current regulators don’t match the pace of global market changes. Over the years, DRW’s crypto arm, Cumberland, bought 70,000 BTC in a US government auction of Silk Road assets. That stash is worth about $7.7 billion today. Related Reading: Bitcoin To $1 Million? Michael Saylor Laughs Off Crypto Winter Fears Featured image from Digital Watch Observatory, chart from TradingView
