MicroStrategy’s Michael Saylor Settles Income Tax Fraud Case

Michael Saylor did not pay any income taxes to Washington despite living there from 2005 through 2020, the attorney general for the District of Columbia said.

Historic Settlement

The attorney general for the District of Columbia reached a $40 million settlement with Michael Saylor and the software company he founded, MicroStrategy, in what the attorney general’s office said was the largest income tax fraud recovery in Washington history. The settlement, which was announced on Monday, stems from lawsuits filed in 2021 and 2022 accusing Mr. Saylor of evading more than $25 million in income taxes in Washington.

Mr. Saylor enlisted MicroStrategy’s help to file fraudulent forms from 2005 through 2020 that claimed he lived in either Virginia or Florida, states with significantly lower income tax rates, the attorney general’s office said; he did not pay income taxes to the district during that period. MicroStrategy and Mr. Saylor deny any wrongdoing. They agreed to the $40 million settlement, which included interest and penalties, to avoid the expense and time of legal action, according to the settlement.

Denial and Agreement

Mr. Saylor, who is the executive chairman of MicroStrategy, stepped down as chief executive in 2022. As part of a separate agreement between Mr. Saylor and MicroStrategy, he has agreed to pay the full settlement amount, MicroStrategy said in a regulatory filing Monday.

“Michael Saylor and his company, MicroStrategy, defrauded the district and all of its residents for years,” Brian L. Schwalb, the attorney general, said in a statement. “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.”

“As I stated at the time this case began, in 2012 I moved to Florida and made Miami Beach my home. Florida remains my home today, and I continue to dispute the allegation that I was ever a resident of the District of Columbia,” Mr. Saylor said in a statement. “I have agreed to settle this matter to avoid the continued burdens of the litigation on friends, family and myself.”

The lawsuit said that in 2012, “Mr. Saylor embarked on a scheme to fraudulently misrepresent himself to be a resident of Florida,” which has no personal income tax, and bought a house in Miami Beach, obtained a Florida driver’s license and registered to vote in the state.

tax evasion
Michael Saylor reportedly avoided paying income taxes through strategic use of legal tax shelters and by residing in Florida, which has no state income tax. While these actions exploit legal loopholes, they are not considered tax evasion, which involves illegal activities to avoid taxes.

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