Michael Saylor flies from Fort Lauderdale to Washington the week of a tax fraud settlement deadline

Michael Saylor flew from Fort Lauderdale to Washington, D.C., on May 22, 2026, aboard the Bombardier Global Express N3877, a 1-hour 47-minute hop that landed near Dulles just before dawn. The flight arrives the same week a $40 million settlement payment is due to the District of Columbia in the tax fraud case brought by Attorney General Brian Schwalb, per the D.C. Office of the Attorney General [oag.dc.gov](https://oag.dc.gov/release/attorney-general-schwalb-secures-40-million). The settlement, announced in June 2024, resolved allegations that Saylor pretended to live in Florida while actually residing in a Georgetown penthouse, evading more than $25 million in income taxes from 2005 through 2020.

Saylor’s return to the Washington area is notable given the case’s reliance on FAA flight records of N3877 as evidence of his physical presence in the District. The aircraft, registered to an LLC at Strategy Inc. headquarters, was cited in the complaint as an “almost perfect representation” of Saylor’s travel to and from D.C. [wtop.com](https://wtop.com/dc/2022/08/dc-ag-sues-local-billionaire-over-taxes/). The settlement requires Saylor and MicroStrategy to pay $40 million, the largest income tax recovery in District history, though they admitted no liability.

This trip follows a pattern of frequent shuttling between Florida and the D.C. area. In the past week alone, N3877 flew from Washington to New York, then to Fort Lauderdale, before returning to Dulles. Saylor’s primary residence remains Villa Vecchia in Miami Beach, but the Georgetown penthouse at Trigate remains a recurring destination, as documented by both flight logs and social media posts.