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MicroStrategy, Michael Saylor Reach $40M Settlement in Tax Evasion Case

In June 2024, news surfaced that MicroStrategy’s CEO, Michael Saylor, reached a $40 million settlement with the attorney general for the District of Columbia, ending a lawsuit accusing him of evading income tax. 

The settlement, reportedly the largest income tax fraud recovery in the district, resolved allegations that Saylor had not paid income taxes in DC for over a decade. 

The lawsuit claimed that Saylor’s company, MicroStrategy, aided in evading more than $25 million in DC income tax. This legal ordeal led Saylor to step down as CEO in August 2022 but remain as executive chairman and chairman of the board of directors. 

Despite the controversy, Saylor continued to promote MicroStrategy as a pro-Bitcoin company, making significant Bitcoin purchases, including 12,000 BTC in March 2024 through an $800 million convertible note offering. 

MicroStrategy’s Bitcoin holdings, totaling 214,400 bitcoins as of May 1, 2024, were acquired at an average purchase price of $35,000 per BTC, amounting to around $7.5 billion. Saylor’s journey to becoming a major Bitcoin advocate began in 2020 when he invested $175 million to acquire 17,732 BTC. Prior to this, Saylor had expressed skepticism about Bitcoin’s future, suggesting in 2013 that without a credible sponsor, Bitcoin could face regulatory challenges leading to its demise.

June 2024, Cryptoniteuae

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Vaibhavv Ali
Vaibhavv Ali

Vaibhavv Ali is the founder and editor of Cryptonite (cryptonite.ae), an independent digital-asset news and analysis publication with a UAE focus. He covers virtual-asset regulation — VARA, ADGM and the UAE Central Bank — alongside real-world-asset tokenization, stablecoins and agentic AI in finance. Every Cryptonite article is human-edited and its sources are linked. He is also a celebrated speaker and host.

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