Strategy shares resumed their decline this week after failing to hold gains made earlier in May. The stock traded near $150 as investors assessed Bitcoin weakness, recent treasury activity, and concerns surrounding the company’s preferred-share obligations.
Market attention also increased after on-chain data showed a transfer of Bitcoin from Strategy-controlled wallets to Coinbase Prime.
The MSTR stock chart is forming a classic head-and-shoulder pattern, which could eventually trigger a sharp drop even further. This could potentially lead to a bearish reversal ahead, as per the below chart.
MSTR stock head-and-shoulder | Source: CoinForge
According to the analyst, the stock has already tested the pattern’s neckline once and could make another attempt to break below the key support level. A confirmed breakdown could increase the risk of a sharper decline in Strategy share price.
The analyst noted that the outlook for Strategy stock remains closely tied to the performance of Bitcoin. Market participants are now watching whether Bitcoin can maintain its strength. Any further weakness in the BTC price could add pressure to Strategy (MSTR) stock price and influence the outcome of the developing chart pattern.
If BTC falls further, Michael Saylor could be forced to sell part of his holdings, as per market experts. Many believe that it could potentially lead to a death spiral affecting the MSTR stock price.
Speculation around a potential Bitcoin sale by Strategy has intensified after blockchain tracking data showed the company transferred 411.48 BTC. On-chain data shows that the company has moved over $30 million worth of BTC to Coinbase Prime.
Strategy Moves Bitcoins | Source: Arkham Intelligence
The transfer has fueled market discussion over whether Strategy could reduce its Bitcoin holdings, despite the company’s long standing commitment to its Bitcoin treasury strategy. Meanwhile, prediction market platform Polymarket currently shows an 84% probability that Strategy will sell Bitcoin before December 31, 2026.
Neither Michael Saylor, nor Strategy, has given any official reason behind moving these Bitcoins. During an interview earlier this month, Saylor said that if Strategy ever needs to sell a small portion of its Bitcoin holdings, the purpose would be to realize capital gains and fund dividend payments related to its STRC preferred stock.
Arca CIO Jeff Dorma criticized the financial position of Strategy, arguing that the company’s capital structure has become increasingly strained. Dorman estimated that Strategy’s roughly $15 billion in preferred stock obligations carry approximately $1.5 billion in annual dividend commitments.
According to Dorman, the company previously raised around $2 billion through stock sales to reduce near term default concerns. However, he claimed that Strategy later used a portion of that cash to repurchase its 2029 convertible bonds rather than preserving funds for future dividend payments.
He thus warned MSTR shareholders, as well as holders of its preferred stock, and investors exposed to Bitcoin could face increasing pressure. If BTC falls further, Dorman thinks that the group can face significant losses over the coming months.
On the other hand Bitcoin critic Peter Schiff challenged claims that Strategy secured a favorable deal through its convertible bond repurchase program. Schiff argued that the company effectively prepaid a zero interest loan two years before maturity at close to its present value.
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