Michael Saylor flies from Miami to the Bahamas, but the story is in the District

Michael Saylor flew from Miami International to San Andros Airport in the Bahamas on May 28, a 23-minute leg in his Bombardier Global Express N3877 that deposits him about 160 miles from Miami Beach.

The same week, Saylor is due to appear in the D.C. Court of Appeals for oral argument in the District’s long-running tax-evasion case against him, per a docket entry from the D.C. Office of Tax and Revenue. The District alleges Saylor owes more than $75 million in unpaid income taxes from 2005 to 2020, using FAA flight records of N3877 as evidence he was physically present in Washington more than he claimed. Saylor’s lawyers have argued his primary residence is Miami, though the D.C. Attorney General has pointed to his Georgetown penthouse as his true home base.

The Bahamas trip is an outlier in Saylor’s recent pattern: over the past two weeks his Global Express has shuttled almost exclusively between Miami, the Washington area, and New York. A short getaway to San Andros—with no known conference or business meeting on the public calendar—reads more like a pause before a courtroom fight than a boardroom move.