D.C.’s bitcoin king: Yachts, penthouses, a python — and tax dodging?

Michael Saylor lived large while allegedly paying no D.C. income tax. Here’s how whistleblowers unraveled what could be one of the largest tax scams in city history.

By Justin Jouvenal

November 14, 2022 at 7:00 a.m. EST

Michael Saylor, chairman of MicroStrategy, speaks during the Bitcoin 2022 conference in Miami on April 7. (Eva Marie Uzcategui/Bloomberg)

12 min

Michael Saylor amassed a multibillion-dollar fortune, splurging to combine three Georgetown penthouses into a palatial 7,000-square-foot residence, snapping up a 154-foot yacht dubbed Mr. Terrible and throwing lavish soirees including one where he was draped with an albino python.

All the while, the tech titan did not pay income tax in the District for years and bragged about it to friends, anonymous whistleblowers allege. They said he told people they were “fools” if they did not buy a home in Florida as he did and claim to live there. The state has no income tax.