Michael Saylor lands at Dulles the same week a DC tax trial looms

Michael Saylor flew from KGAI in Gaithersburg, Maryland, to KIAD at Washington Dulles International Airport on June 1, 2026 — a 10-minute hop in the Bombardier Global Express that barely cleared 4,000 feet. The flight, logged at 280 knots and arriving at 1:14 PM local, marks another short Northeast leg for the Strategy Inc. executive chairman.

The brevity of the trip may be more logistical than strategic, but the wider context is a legal one. Saylor faces a lawsuit from the District of Columbia Attorney General, filed in August 2022, alleging he evaded more than $25 million in DC income taxes between 2005 and 2020 by claiming Florida residency while living in a Georgetown penthouse. FAA flight records of N3877, the same aircraft used today, have been cited as evidence of his physical presence in the district, per court filings. The case has potential liability exceeding $75 million.

The flight pattern in recent days shows a familiar rhythm: Miami Beach to the Bahamas and back, then a dash to the DC area. Saylor maintains Villa Vecchia in Miami Beach as his primary residence, but the DC Attorney General argues he actually resides at 'Trigate' in Georgetown. Whether this June 1 hop was a return home or a prelude to the next hearing, the N3877 flight log remains a key Exhibit A.