Jeanine Montgomery, who serves as Vice President and Chief Accounting Officer at Strategy Inc (NASDAQ:MSTR), disposed of 470 shares of the company’s Class A Common Stock on March 24, 2026, netting approximately $65,016. According to the Form 4 filed with the Securities and Exchange Commission, the sales were carried out across multiple transactions at prices between $137.73 and $139.453 per share.
The filing states the share sales were connected to Montgomery’s need to meet tax obligations that arose when previously granted equity awards vested. The regulatory disclosure also records that on March 23, 2026, Montgomery acquired 1,560 shares of Class A Common Stock upon the exercise of restricted stock units.
Strategy Inc’s stock is trading at $139.12 at the time of writing, a level that follows a difficult stretch for the $48.21 billion company. Over the prior 12 months the shares have fallen 58%, a decline noted in market data included in the original filing and related commentary.
Separately, Strategy Inc has been active in augmenting its Bitcoin position. Between March 9 and the most recent Sunday referenced in company disclosures, the firm purchased nearly $1.6 billion worth of Bitcoin, its largest single acquisition since January. That tranche comprised 22,337 Bitcoin and was financed with $400 million in proceeds from common stock sales and $1.2 billion from sales of Stretch perpetual preferred shares.
In addition to that acquisition, Strategy Inc bought another $76.5 million of Bitcoin between March 16 and March 22, funding this purchase with proceeds from at-the-market sales of its Class A common stock. Company disclosures present these purchases as part of an ongoing effort to expand the firm’s Bitcoin portfolio.
Market participants and sell-side analysts have been active on the name. Bernstein SocGen Group maintained an Outperform rating and left a $450.00 price target, citing a constructive view on Bitcoin’s prospects. Texas Capital Securities initiated coverage with a Buy rating and a $200.00 target, noting Strategy Inc’s positioning in digital asset treasury management. Similarly, B. Riley began coverage with a Buy rating and a $175.00 price target, highlighting the scale of the company’s Bitcoin holdings, which were reported at approximately 721,000 Bitcoin.
Context and implications
The transaction by Montgomery is recorded as a tax-driven sale tied to routine vesting events rather than an unsolicited divestiture. The timing coincides with extensive corporate activity around digital-asset accumulation and renewed analyst attention. The filings disclose both the small-scale insider transactions and the substantially larger corporate purchases of Bitcoin.
While the insider sale involves a modest number of shares relative to the company’s market capitalization, the broader company actions - sizable Bitcoin purchases funded through equity and preferred share issuances - remain material to Strategy Inc’s balance sheet allocation and investor narrative.