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Donald Trump’s MSTR Trade Raises Eyebrows as Strategy Shares Rally 83%

Published 24 September 2026
Giuseppe Ciccomascolo
Authors

Key Takeaways

  • President Donald Trump’s investment accounts bought Strategy shares twice in late July, including a $50,001-$100,000 purchase on July 27.
  • MSTR has climbed about 83% since the smaller July 24 purchase, while the larger July 27 trade is up roughly 70% based on closing prices.
  • The Trump Organization says independent financial institutions manage the accounts and that Trump and his family do not select, direct, or approve individual investments.

President Donald Trump’s investment accounts bought shares of Bitcoin giant Strategy near their summer lows, weeks before MSTR staged a rally of more than 80%.

A federal ethics filing published Sept. 22 reveals two purchases of Strategy (formerly MicroStrategy) in late July. The timing has attracted attention because the company is the world’s largest corporate Bitcoin holder and its shares have surged alongside Bitcoin’s recent recovery.

The filing does not establish that Trump personally chose the trades. The Trump Organization has said outside financial institutions manage the accounts without Trump, his family or the organization directing individual investment decisions.

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Trump Accounts Sold MSTR, Then Bought Back Near the Bottom

The trading pattern started with sales.

Trump’s accounts sold between $16,002 and $65,000 worth of Strategy shares between June 23 and June 24. Two days later, MSTR touched $81.81, its lowest intraday level of the summer.

Another sale worth between $1,001 and $15,000 followed on July 8.

The accounts then reversed course.

On July 24, they purchased between $1,001 and $15,000 of MSTR. A considerably larger purchase worth $50,001 to $100,000 followed on July 27, according to the disclosure.

Strategy closed at $91.67 on July 24. By Sept. 22, it had reached $167.33, representing an approximately 83% increase, according to calculations highlighted by political trading tracker Quiver Quantitative. The July 27 purchase, made when MSTR closed at $98.65, has gained roughly 70% on the same basis.

The disclosures provide transaction ranges rather than exact amounts, share counts, or execution prices. They also do not reveal whether the accounts still hold the shares.

Bitcoin Rally Sends Strategy Higher

The MSTR rally coincided with a sharp turnaround in Bitcoin.

Bitcoin climbed above $86,000 this week, helping lift crypto-linked stocks. Strategy jumped another 9.5% on Sept. 21 as Bitcoin broke higher.

Strategy has also returned to accumulating Bitcoin.

The company bought 4,603 BTC for $369.7 million between Aug. 24 and Aug. 30, at an average price of $80,318 per BTC. That brought its holdings to 845,050 BTC at the end of August.

Its holdings have since risen further. Strategy held 846,000 BTC as of Sept. 21, acquired for approximately $63.8 billion at an average cost of $75,416 per Bitcoin.

That enormous Bitcoin position means movements in BTC can have an outsized impact on MSTR.

Trades Add to Existing Scrutiny

The Strategy purchases arrive amid broader scrutiny of trading activity reported through Trump’s investment accounts.

Sen. Elizabeth Warren and Rep. Robert Garcia raised conflict-of-interest concerns in an August letter concerning Trump’s disclosed securities transactions and their proximity to government actions involving some of the companies. Those concerns are allegations by the lawmakers, not evidence that the Strategy trades involved non-public information or improper conduct.

The Trump Organization disputes the premise that Trump controls the transactions. It says the assets are held in discretionary accounts managed by third-party financial institutions.

For MSTR specifically, the disclosure reveals a striking timing: the accounts bought Strategy near its summer lows, ahead of an 83% rally.

It does not establish who selected the trades, why they were made, or whether the accounts continue to hold the position.

Disclaimer: The information provided in this article is for informational purposes only. It is not intended to be, nor should it be construed as, financial advice. We do not make any warranties regarding the completeness, reliability, or accuracy of this information. All investments involve risk, and past performance does not guarantee future results. We recommend consulting a financial advisor before making any investment decisions.
Giuseppe Ciccomascolo

Giuseppe Ciccomascolo began his career as an investigative journalist in Italy, where he contributed to both local and national newspapers, focusing on various financial sectors.

Upon relocating to London, he worked as an analyst for Fitch's CapitalStructure and later as a Senior Reporter for Alliance News. In 2017, Giuseppe transitioned to covering cryptocurrency-related news, producing documentaries and articles on Bitcoin and other emerging digital currencies. He also played a pivotal role in establishing the academy for a cryptocurrency exchange website. Crypto remained his primary area of interest throughout his tenure as a writer for ThirdFloor.

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