Michael Saylor lands in Teterboro the week Strategy mulls first-ever Bitcoin sale

Michael Saylor flew from Washington Dulles to Teterboro, New Jersey on the evening of May 21, 2026, a 57-minute hop aboard N3877, his Bombardier Global Express. The flight lands in the New York metro area the same week his firm, Strategy Inc., is navigating the fallout from a bombshell earnings call where Saylor and CEO Phong Le admitted the company would consider selling Bitcoin for the first time since adopting its corporate Bitcoin model in August 2020, per a detailed report from [tokenist.com](https://tokenist.com/saylor-strategy-bitcoin-treasury-rebalance/). The shift, framed as “active capital recycling,” marks a structural departure from the absolute no-sell stance that defined Strategy’s digital-asset treasury model and has drawn intense scrutiny from the crypto and investment communities.

The New York area is the natural venue for the investor meetings and credit-market conversations that such a strategic pivot demands. Strategy holds roughly 815,000 BTC purchased at a blended cost near $75,500 per coin, and its balance sheet carries $4.1 billion in convertible notes due in 2027–2028 — a debt load that, as [protos.com](https://protos.com/strategy-could-own-more-bitcoin-than-satoshi-by-september/) notes, is the mechanism forcing the rethink. A junk-level credit rating from S&P Global Ratings in October 2025 had already flagged the risk of forced liquidations; the May 5 earnings call confirmed that selling BTC for USD or to service debt is now on the table.

The Teterboro arrival follows a pattern of frequent DC–Miami–DC shuttling; earlier this week Saylor flew from Morocco back to Dulles on May 20, then to Miami on May 15. The New York trip suggests a deliberate push to sell the revised strategy to institutional investors and credit desks before any actual sale hits the market. Saylor has publicly insisted he intends to “buy more Bitcoin than you sell,” as [u.today](https://u.today/buy-more-bitcoin-than-you-sell-michael-saylor-makes-u-turn-amid-22-day-dry-spell) reported, but the dry spell in purchases — 22 days and counting — has the market watching closely.