Did MicroStrategy make the worst bitcoin purchase in 2025?

MicroStrategy's latest bitcoin transaction has quickly attracted attention. Just one day after the company disclosed this large purchase, the price of bitcoin plummeted.

On December 14, MicroStrategy announced it had acquired 10,645 bitcoins for approximately $980.3 million, with an average purchase price of $92,098 per bitcoin. At that time, bitcoin was trading near its local high.

At least in the short term, this was an ill-timed purchase.

The timing was truly unfortunate. Just one day later, according to reports, after the Strategy acquisition, the price of bitcoin dropped to around $85,000, even briefly falling below that range. At the time of writing, bitcoin remains below $80,000.

The drop in bitcoin occurred amid a broader macroeconomically driven sell-off, which was triggered by... concerns over a Bank of Japan rate hike, leveraged liquidations, and market makers de-risking. MicroStrategy's acquisition happened just before this series of events unfolded.

As bitcoin's price fell, MicroStrategy's stock price also plunged. Over the past five trading days, the stock has dropped more than 25%, significantly underperforming bitcoin itself.

Although the stock rebounded slightly today, it remains well below its level prior to the acquisition announcement.

The Data Behind the Concerns

As of now, MicroStrategy holds 671,268 BTC at a total cost of approximately $5.033 billions, with an average price of $74,972 per coin.

In the long run, the company will still remain profitable.

However, short-term market performance is crucial. With bitcoin's price near $85,000, the latest batch of bitcoins is already worth less than their purchase price on paper.

MicroStrategy's mNAV is currently about 1.11, meaning the stock is trading at only about an 11% premium over the value of its bitcoin holdings. As bitcoin's price has fallen and stock investors reassess risk, this premium has quickly narrowed.

Why Did the Market React So Strongly?

Investors are not questioning MicroStrategy's bitcoin investment thesis, but rather its timing and risk management.

The macro risks that triggered bitcoin's drop had already been signaled. The market had previously warned that the Bank of Japan might raise rates, posing a threat to yen carry trades for several weeks.

Historically, bitcoin has suffered significant sell-offs during Bank of Japan monetary tightening cycles. This time was no exception.

Critics argue that MicroStrategy failed to wait for macroeconomic clarity. The company appeared to buy aggressively near resistance levels just as global liquidity was tightening.

Was This Really a Mistake?

That depends on the timing.

From a trading perspective, this was a poorly timed purchase. Bitcoin fell immediately, and due to leverage, market sentiment, and the narrowing of the NAV premium, the stock suffered even greater losses.

From a strategic perspective, MicroStrategy has never tried to time the bottom. The company has always adhered to a strategy of long-term accumulation rather than short-term price optimization.

CEO Michael Saylor has repeatedly argued that owning more bitcoin is more important than entry precision.

The real risk does not lie in the purchase itself, but in what happens afterward.

If bitcoin's price stabilizes and macroeconomic pressures ease, MicroStrategy's latest purchase will gradually blend into its long-term cost basis. However, if bitcoin's price falls further, this 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.