Michael Saylor Faces Backlash Over $27M Private Jet Buy

4th December – Michael Saylor is under renewed criticism as Strategy revealed a $27 million deposit for a new corporate jet. The disclosure, made in a recent SEC filing, has sparked debate about the company’s spending priorities. Many investors are questioning whether this move aligns with Strategy’s Bitcoin-first identity, especially given the sharp downturn in both Bitcoin and the company’s stock price.

Shareholders Push Back on Spending During Volatility

According to Strategy’s Form 10-Q, filed on December 3, the company made a $27 million deposit toward a new private aircraft during the nine months ending September 30, 2025. This spending comes during a turbulent period for Strategy’s stock, which has fallen more than 40% year-to-date and nearly 30% in November alone.

Critics argue that the company should have focused its resources on Bitcoin accumulation, not executive comforts. Strategy had just raised $1.478 billion in late November by selling over 8.2 million new shares. Most of that money was allocated to a $1.44 billion cash reserve for debt interest and preferred dividends. Still, the jet deposit, funded from general corporate funds, struck many as poorly timed.

Several analysts noted that the funds used for the jet could have purchased roughly 300 to 350 Bitcoin at current prices.

Strategy’s Valuation Continues to Slide

As of December 4, Strategy’s stock price hovered around $171, down from a July high of $300. The company now trades at a discount to its Bitcoin holdings. Its modified net asset value (mNAV) has dropped to just 0.87x, signaling that the market values the company below the value of its Bitcoin reserves.

Key metrics as of early December:

• Bitcoin holdings: 650,000 BTC
• Total spent on BTC: $48.4 billion
• Unrealized gains: Around $7.6 billion
• Average BTC cost: $74,436
• Debt leverage: 1.11x

Meanwhile, the company has faced increasing scrutiny for shareholder dilution. Many investors believe the once-reliable strategy of issuing stock to buy Bitcoin has begun to falter. The recent creation of a USD Reserve marked a shift in how Strategy deploys raised capital.

Src: Arkham

Community Divided Over Jet Purchase

Supporters argue that the jet is a minor expense relative to the company’s overall balance sheet. They also stress that Strategy operates globally and has legitimate needs for executive travel. In this view, the $27 million represents only a fraction, about 0.14% of its total Bitcoin spending for the year.

However, others believe the optics are damaging. With market sentiment fragile and Strategy’s stock declining, any move perceived as non-essential draws intense scrutiny. Critics see the jet deposit as out of sync with Strategy’s core messaging and its retail investor base.

Additionally, the upcoming MSCI review could further impact Strategy’s standing. A potential removal from indices in January 2026 may trigger up to $8.8 billion in passive outflows, according to JPMorgan. Saylor has acknowledged the issue and is reportedly in discussions with MSCI, though he has attempted to downplay the possible effects.

Saylor Stands Firm Despite Concerns

In a December 3 interview with Reuters, Saylor reaffirmed his position. He described Strategy as “volatile by design,” given its high Bitcoin leverage. He also noted that a 30 to 40 percent decline in Bitcoin could lead to even steeper drops in Strategy’s stock. While he has consistently stated that the company will not sell Bitcoin, new filings now allow for BTC sales if mNAV falls below 1x – a notable shift from previous pledges.

Saylor’s recent social media activity has hinted at possible strategic shifts. His post, “What if we start adding green dots?” suggests a focus on building cash reserves for future Bitcoin buys.

Overall, the situation reflects growing tensions between Strategy’s operational decisions and its identity as a Bitcoin proxy. Investors will likely continue monitoring how the company balances executive spending with its crypto-first mission.