MicroStrategy and Michael Saylor Settle Tax Evasion Lawsuit in $40 Million Deal

Tax law.
  • Bitcoin lover and founder of MicroStrategy, Michael Saylor, has settled with the District of Columbia (DC) in a whopping US$40m deal.
  • The State accused Saylor of avoiding taxes by misrepresenting his residential status.
  • His company, MicroStrategy, was also embroiled in the scheme by signing off on documents with his allegedly falsified residence.
  • Despite the hefty settlement, Saylor claims he is still innocent and only paid up to avoid the toll of a lawsuit on his family and friends.

Name a better combo – rich people and not paying taxes.  

There’s a reason that clearly American companies are often registered in nations like Seychelles, Ireland and the Cayman Islands thanks to their extremely liberal tax laws. However, this time, a supposed case of mistaken residential status is behind a US$40m (AU$60m) tax settlement with a US Court. 

Related: Michael Saylor Revises View on Ether, Predicts ETF Will Accelerate Crypto Adoption

Saylor Maintains Innocence, Settlement to “Avoid Burden”

Michael Saylor is revered among the crypto industry as being THE Bitcoin maximalist to end all maximalists. The founder of MicroStrategy (who stepped down as CEO in 2022) pushed his company to become by far the largest institutional holder of BTC in the world


There is no greater adoration in the universe than the one Saylor holds for Bitcoin.

But, according to the District of Columbia, the esteemed businessman hasn’t been on his best behaviour. The attorney general alleged that Michael Saylor owed the State up to US$25m (AU$37m) in unpaid taxes dating back to 2005.  

Specifically, Saylor was accused of misleading the tax office by claiming to be a resident of Florida (a state with much lower income tax rates) instead of DC. His company, MicroStrategy, became embroiled in the debacle after being accused of helping Saylor cover up his true residential status.

Michael Saylor and his company, MicroStrategy, defrauded the district and all of its residents for years…Indeed, Saylor openly bragged about his tax-evasion scheme, encouraging his friends to follow his example and contending that anyone who paid taxes to the district was stupid.

DC attorney general, Brian Schwalb

Saylor maintained that he’d been living in Florida since 2012 and that he’d done nothing wrong. However, he eventually yielded and settled with the District of Columbia to the tune of US $40m (AU $60m).

Despite most people assuming settlement = guilty, Saylor was quick to publicly denounce such associations. 

I continue to dispute the allegation that I was ever a resident of the District of Columbia. I have agreed to settle this matter to avoid the continued burdens of the litigation on my friends, family and myself.

Michael Saylor

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Ben Knight

Ben Knight

Ben Knight is a writer and editor from Melbourne with a passion for all things music and finance. He enjoys turning complex topics – especially the technical details of cryptocurrency – into digestible bites that anybody can understand. He acquired his Master’s in Writing, Editing and Publishing from RMIT in 2019 and has run his own creative writing business ever since.

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