Michael Saylor flies from Miami to DC amid Strategy's potential Bitcoin sell-off

Michael Saylor flew from Miami International Airport to Washington Dulles International Airport aboard his Bombardier Global Express N3877 early on May 12, 2026. The two-hour, twenty-minute flight covered the familiar route between his claimed Florida residence and the nation's capital area, reaching a maximum altitude of 45,050 feet and speed of 520 knots.

The trip coincides with turbulence at Strategy Inc., where Saylor serves as executive chairman. Per a CNBC report on May 5, the company broke from its long-standing 'never sell' approach to Bitcoin, with Saylor stating during the Q1 2026 earnings call that Strategy may liquidate some of its 818,334 BTC holdings—valued at over $75 billion—to fund dividends. As covered by Bitcoin.com News, this reversal comes amid a $12.5 billion quarterly loss, prompting speculation on opportunistic sales in May.

Saylor's journeys often trace business imperatives near Strategy's Tysons, Virginia, headquarters, just outside DC. Recent flights show him lingering in Bahamian waters on May 11 before heading to Miami, suggesting a weekend escape before returning for high-stakes decisions. This DC pull echoes past patterns, including the 2024 $40 million tax fraud settlement with the District, per the Washington Post, underscoring his ties to the area despite Miami claims.