Monday, September 15, 2025

MicroStrategy, Michael Saylor Sued by Washington DC Over Tax Fraud

MicroStrategy (NASDAQ: MSTR) founder and former executive chairman Michael Saylor was slapped with a lawsuit by Washington DC., over allegedly failing to pay taxes on hundreds of millions of dollars in earnings while he resided in the region for over a decade.

According to a tweet by Attorney General Karl A. Racine, the District of Columbia is suing the former billionaire over failing to abide by the state’s tax laws. According to a copy of the complaint seen by CoinDesk, Saylor made it appear as if he resided in Florida and Virginia by purchasing property and registering as a voter in those states, meanwhile still living in a Washington penthouse for at least 183 days per year, which is the minimum number of days required to be considered a statutory resident.

Further, the lawsuit also alleges that MicroStrategy— under Saylor’s instruction, reported to the IRS that his residence was in Florida. “Concerned about MicroStrategy’s involvement in Defendant Saylor’s fraudulent scheme to avoid District taxes, in or about 2014, MicroStrategy’s then-Chief Financial Officer undertook a count of the number of days that Defendant Saylor spent in Florida as compared to the District and found that because Saylor spent the majority of each year in the District, MicroStrategy could not justify misreporting Saylor’s residency to federal tax official,” read the complaint.

Racine’s office accuses Saylor of failing to pay over $25 million in taxes, and is demanding that the MicroStrategy founder is held liable for back taxes, treble damages, and civil penalties. The latest lawsuit comes at an unfortunate time for Saylor, who recently lost his billionaire status and subsequently stepped down from the CEO position after the company’s $1 billion purchase of bitcoin back in 2020 did not fare well during the recent crypto crash.

Information for this briefing was found via Twitter. The author has no securities or affiliations related to this organization. Not a recommendation to buy or sell. Always do additional research and consult a professional before purchasing a security. The author holds no licenses.

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