Michael Saylor flies to Miami after a crypto regulation summit in Morocco

Michael Saylor flew from Hickory Tree Farms Airport in Middleburg, Virginia, to Miami International Airport late Thursday night, arriving just before 1 a.m. on May 28. The two-hour-and-fifteen-minute hop aboard N3877—the 2008 Bombardier Global Express registered to his company—is a familiar route for the crypto billionaire, whose DC-to-Miami pattern has drawn scrutiny from the District of Columbia Attorney General in a long-running tax evasion suit.

The same week Saylor touched down in Miami, the U.S. Securities and Exchange Commission announced a new wave of crypto-related enforcement actions, per a Reuters report published May 27. The SEC has spent years tangling with Saylor’s firm, Strategy Inc., over its Bitcoin treasury disclosure practices. Saylor, who holds the world’s largest public-company Bitcoin hoard, has made no secret of his belief that U.S. regulation lags behind innovation—a stance he reiterated at a blockchain conference in Marrakech earlier this month, where his aircraft was tracked on a round-trip to Morocco from May 15 to May 22.

That Morocco excursion ended with his jet landing in Washington on May 22, then immediately repositioning to New York, then back to Miami the same day—a familiar shuttle between his alleged primary residence in Georgetown and his claimed homestead in Miami Beach. The latest flight settles him back at KMIA, where his Bombardier sits within easy reach of both Villa Vecchia and the crypto media cycle.