The lawsuit, which Racine filed Aug. 22 in D.C. Superior Court, alleges that Saylor has for years fraudulently claimed to be a resident of lower-tax jurisdictions despite living in a 7,000-square-foot penthouse on the Georgetown waterfront. The complaint further alleges that MicroStrategy, despite knowing Saylor was a D.C. resident, conspired in the scheme “instead of accurately reporting his address to local and federal tax authorities and correctly withholding District taxes.” Both Saylor and MicroStrategy issued statements on Wednesday, denying the allegations in the suit.
The complaint alleges that Saylor purchased the Georgetown property in 2005 before buying two adjoining penthouse units, combining them into a single residence Saylor calls “Trigate,” and also purchased a penthouse unit in Adams Morgan. Beginning in 2012, according to the complaint, Saylor purchased a home in Miami Beach, obtained a Florida driver’s license and registered to vote there despite living primarily in D.C. The suit alleges he did not pay income taxes in D.C. at any point between 2005 and 2021, despite social media posts over the years that indicate he lived in D.C. and considered it home.
“Since at least 2012, Saylor has bragged to his confidants about his successful plan to create the illusion of residing in Florida in order to evade the District’s personal income taxes,” the complaint reads. The lawsuit alleges that MicroStrategy abetted in the fraud through an agreement to list Saylor’s residence on federal tax forms as his house in Florida, despite knowing he lived in D.C., “actively assisting Saylor to avoid his obligation to pay taxes owed to the District.” (Florida has no state individual income tax).
Saylor said in his statement that he bought the Miami Beach home a decade ago after moving from Virginia.
“Although MicroStrategy is based in Virginia, Florida is where I live, vote, and have reported for jury duty, and it is at the center of my personal and family life,” he wrote. “I respectfully disagree with the position of the District of Columbia, and look forward to a fair resolution in the courts.”
Saylor founded MicroStrategy in 1998 and served as its CEO until earlier this month when the publicly traded company announced that he would take on a new role as its executive chairman. In an Aug. 2 news release announcing the leadership change, MicroStrategy said that Saylor would also remain chairman of its board of directors.
MicroStrategy in its own statement denied the allegations and vowed to “defend aggressively against this overreach.”
“The case is a personal tax matter involving Mr. Saylor,” the statement said. “The Company was not responsible for his day-to-day affairs and did not oversee his individual tax responsibilities. Nor did the Company conspire with Mr. Saylor in the discharge of his personal tax responsibilities.”
Racine’s office said the lawsuit was brought under the city’s recently expanded False Claims Act, which the D.C. Council last year amended to include tax-related issues, and incentivizes whistleblowers to identify tax fraud. Racine said the law also enables the court to levy a punishment up to three times the amount of taxes evaded, and that between the unpaid income taxes and other penalties his office is seeking to recover from Saylor and MicroStrategy, damages in the case could amount to more than $100 million.
The lawsuit builds on a similar complaint filed against Saylor by whistleblowers in D.C. Superior Court last year, which was unsealed Wednesday. Racine’s office said it independently investigated the tax fraud allegations and intervened in the whistleblower complaint, filing its own lawsuit against Saylor and MicroStrategy.