Michael Saylor lands in Miami after a Teterboro trip, the same week Strategy accelerates its Bitcoin buying spree

Michael Saylor flew from Teterboro, New Jersey, to Miami on the night of May 21, arriving just after 10:40 p.m. local time. The two-and-a-half-hour hop in N3877, a 2008 Bombardier Global Express, came after a midday flight into Teterboro from the Washington, D.C., area — a short shuttle that fits a long pattern of movement between corporate bases and personal addresses.

Saylor lands back in Miami the same week Strategy Inc., the company he co-founded and chairs, disclosed it had purchased 34,164 Bitcoin in a single week — a 2026 record, per Protos. That buying pace, if sustained, would see Strategy hold more Bitcoin than the pseudonymous creator Satoshi Nakamoto by September. The company now holds 815,061 BTC, bought at an average of $75,527 per coin, and is funding the purchases through a mix of common stock and a new preferred offering, STRC, which the company markets aggressively as a high-yield alternative.

Saylor has claimed Florida as his primary residence since purchasing Villa Vecchia in Miami Beach in 2012, though the D.C. Attorney General’s Office has alleged in a lawsuit that Saylor actually lives in a Georgetown penthouse and owes more than $25 million in evaded income taxes — a case that cites flight records of N3877 as evidence of his physical presence in the District. The flight from Teterboro, rather than from Washington, keeps the tail’s recent geography ambiguous: the jet had just returned from Marrakech, Morocco, days earlier.