MicroStrategy’s latest Bitcoin buy has quickly come under scrutiny. Just one day after the firm disclosed a major purchase, Bitcoin fell sharply.

On December 14, MicroStrategy announced it had acquired 10,645 BTC for roughly $980.3 million, paying an average price of $92,098 per coin. At the time, Bitcoin was trading near local highs.

A Poorly Timed Buy, At Least in the Short Term

The timing was unfortunate. Only a day after Strategy’s reported purchase, Bitcoin had dropped toward the $85,000 range, briefly trading even lower. At the time of writing BTC remains below $80,000.

Bitcoin’s decline came amid a broader macro-driven sell-off, fueled by Bank of Japan rate-hike fears, leverage liquidations, and market-maker de-risking. MicroStrategy’s purchase landed just ahead of that cascade.

As Bitcoin slid, MicroStrategy shares fell sharply. Over the past five trading days, the stock dropped more than 25%, significantly underperforming Bitcoin itself.

While shares saw a modest rebound today, they remain far below levels seen before the purchase announcement.

MSTR Stock Prices Over The Past Week. Source: Google Finance

The Numbers Behind the Concern

As of now, MicroStrategy holds 671,268 BTC, acquired for approximately $50.33 billion at an average price of $74,972 per coin.

On a long-term basis, the firm remains deeply in profit.

However, short-term optics matter. With Bitcoin near $85,000, the latest tranche is already underwater on paper.

MicroStrategy’s mNAV currently sits around 1.11, meaning the stock trades only about 11% above the value of its Bitcoin holdings. That premium has compressed rapidly as Bitcoin fell and equity investors reassessed risk.

MicroStrategy mNAV. Source: Saylor Tracker

Why the Market Reacted So Harshly

Investors are not questioning MicroStrategy’s Bitcoin thesis. They are questioning timing and risk management.

The macro risks that triggered Bitcoin’s drop were well telegraphed. Markets had been warning about the Bank of Japan’s potential rate hike and the threat to the yen carry trade for weeks.

Bitcoin has historically sold off aggressively around BOJ tightening cycles. This time was no different.

Critics argue MicroStrategy failed to wait for macro clarity. The firm appeared to buy aggressively near resistance, just as global liquidity conditions tightened.

Was It Actually a Mistake?

That depends on the timeframe.

From a trading perspective, the purchase looks poorly timed. Bitcoin fell immediately, and the stock suffered amplified losses due to leverage, sentiment, and shrinking NAV premium.

From a strategy perspective, MicroStrategy has never aimed to time bottoms. The company continues to frame its purchases around long-term accumulation, not short-term price optimization.

CEO Michael Saylor has repeatedly argued that owning more Bitcoin matters more than entry precision.

The real risk is not the purchase itself. It is what happens next.

If Bitcoin stabilizes and macro pressure eases, MicroStrategy’s latest buy will fade into its long-term cost basis. If Bitcoin drops further, however, the decision will remain a focal point for critics.

MicroStrategy may not have made the worst Bitcoin purchase of 2025. But it may have made the most uncomfortable one.