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Trump calls buybacks “fake” as MicroStrategy’s share‑issuance‑for‑Bitcoin strategy faces a thinning premium, with BTC near $64,360 and MSTR market value around
MicroStrategy’s shares have slid more than 50% over the past year, pulling its market value toward $40 billion, while Bitcoin trades near $64,360 – a level that leaves the company’s Bitcoin holdings close to its average purchase price, eroding the premium that once justified its dilution‑driven model [2].
| At a glance | |
|---|---|
| Bitcoin price | $64,360 |
| MSTR stock decline | >50% YTD |
| Bitcoin holdings | >845,000 BTC (≈4% of supply) |
| Catalyst | Trump’s criticism of buybacks & MicroStrategy’s dilution model |
President Donald Trump reiterated that stock buybacks are a “fake” way to boost share prices, targeting defense contractors with an executive order that bars underperforming firms from repurchasing shares or paying dividends until production improves. The remarks have already rattled defense stocks and revive a broader debate over whether companies should shrink share counts through buybacks or dilute equity to fund growth initiatives such as a corporate Bitcoin treasury [1].
MicroStrategy (now “Strategy”) has taken the opposite route, issuing new common and preferred shares and using the proceeds to buy Bitcoin. This approach has amassed more than 845,000 BTC—the largest public‑company holding—and the Bitcoin now represents over four percent of all BTC in circulation. The firm also repurchased convertible notes at a discount and leaned on preferred‑stock issuances to avoid senior debt, keeping its balance sheet flexible [1][2].
The model hinges on a “flywheel”: issuing stock above the value of its Bitcoin, buying more BTC, and raising Bitcoin‑per‑share (BPS). When Bitcoin’s price was well above the company’s average cost, the premium over net asset value (NAV) supported a higher market cap. With Bitcoin now near $64,360, the premium has thinned, meaning new share sales add little incremental value and the dilution that once propelled gains now offers weaker support, especially amid recent Bitcoin sell‑off pressure [2].
MSTR’s market cap has slipped toward $40 billion, reflecting the loss of the premium that previously justified its high‑growth valuation. The stock fell 3% in after‑hours trading following the latest earnings release, where the company disclosed a $12.5 billion net loss for Q1, driven by the Bitcoin price slump. While the firm maintains a $2.25 billion U.S. dollar reserve to meet dividend and debt obligations, its future valuation will depend on whether Bitcoin climbs back above its cost basis and revives the BPS premium [4].
The clash between Trump’s buyback criticism and MicroStrategy’s Bitcoin‑funded dilution highlights a fundamental question for investors: does a company create real value by expanding its asset base, or merely shift its share price through financial engineering? The answer will hinge on Bitcoin’s price trajectory and the durability of the premium that underpins MicroStrategy’s valuation.
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AI-assisted synthesis by the TrendWatcher Editorial Desk · sourced from 4 outlets · Jun 23, 2026 · How we report
The company made its first Bitcoin purchase in August 2020, investing $250 million as a treasury reserve asset.
As of November 17 2025, MicroStrategy reported owning over 650,000 Bitcoins, worth approximately $59.69 billion.
Michael Saylor, as executive chairman, has driven the Bitcoin acquisition strategy and compared it to a Bitcoin spot leveraged ETF.
The company sold 704 Bitcoins on December 22 2022 for about $11.8 million, marking its first Bitcoin sale.
In 2025, MicroStrategy launched four credit instruments worth $4 billion, described as high‑yield perpetual securities linked to its Bitcoin treasury.