Chad Smith
Strategy (MSTR) shares hit their lowest price in more than two years on Wednesday, dropping below $100 as Bitcoin slid to a two week low and investor concern over the $52 billion Bitcoin accumulator deepened.
At a Glance
- MSTR fell as low as $97.30 on Wednesday, a drop of nearly 5.5% on the day.
- The stock is down about 20% over the past week and more than 38% over the past month.
- Bitcoin slipped to around $60,935, its lowest level in two weeks, and is now more than 50% below its all-time high.
- Strategy's preferred shares (STRC) dropped to $84.35, down 3.4% on the day, after hitting a low of $82.53 the previous week.
- The last time MSTR traded under $100 was March 1, 2024, when Bitcoin was in a similar price range.
A Two Year Low for MSTR
Strategy shares touched $97.30 roughly 30 minutes after Wednesday's opening bell before settling around $98.05, according to Yahoo Finance data. That puts the stock beneath a threshold it hasn't breached since March 1, 2024, a date that is notable for another reason: Bitcoin was trading in the $61,000 to $62,000 range back then too.
The parallel underscores just how far both assets have retreated. Strategy shares peaked above $400 in early 2025, riding the wave of optimism that followed President Donald Trump's crypto-friendly policy signals. Bitcoin itself set an all-time high above $126,000 last October. Both have since given back enormous ground.
Bitcoin Under Pressure
The $60,935 Bitcoin price represents a decline of more than 50% from that record peak. The slide has been driven by a combination of forces: investors pulling money out of Bitcoin ETFs, renewed interest in AI stocks offering higher near term return potential, and a more hawkish tone from the Federal Reserve.
Bitcoin struggled to regain its footing after breaking below $70,000 around the start of June. That weakness coincided with a disclosure that complicated Strategy's public image considerably.
The First Bitcoin Sale in Three Years
Strategy revealed in early June that it had sold some of its Bitcoin holdings for the first time since 2022. The move cracked the "buy and never sell" philosophy that co-founder and executive chairman Michael Saylor has championed publicly for years. Whether that sale was a tactical necessity or a sign of things to come, it rattled investors who had priced in a permanent accumulation strategy.
As the largest corporate Bitcoin holder and the originator of the crypto treasury model that other companies adopted last year, Strategy's actions carry weight in both directions. Its buying helped lift Bitcoin during bull runs; its selling, or even the hint of it, weighs on sentiment when conditions are already fragile.
Preferred Shares Add Another Layer of Risk
Strategy's STRC preferred shares, designed to trade near $100, have become a fresh source of anxiety. These shares have funded billions of dollars in Bitcoin purchases this year, but growing fears that Strategy may need to sell BTC to cover dividend obligations have hammered the instrument.
STRC dropped to a low of $82.53 last week and was trading at $84.35 on Wednesday, down 3.4% on the day. A preferred share trading nearly 16% below its intended par level signals real unease about the company's financial flexibility.
Frequently Asked Questions
Why did MSTR stock fall below $100?
MSTR dropped below $100 on Wednesday as Bitcoin fell to a two week low near $60,935 and investors grew more concerned about Strategy's finances, including fears it may need to sell Bitcoin to fund preferred share dividends. The stock is also down more than 38% over the past month as broader crypto sentiment has weakened.
When did MSTR last trade under $100?
According to Yahoo Finance historical data, the last time Strategy shares closed below $100 was March 1, 2024. Coincidentally, Bitcoin was trading at a similar price then, roughly $61,000 to $62,000.
What is STRC and why does it matter?
STRC is a class of Strategy preferred shares issued to raise capital for Bitcoin purchases. It is designed to trade near $100, but has fallen well below that level amid concern that Strategy could be forced to liquidate Bitcoin holdings to meet its dividend commitments to STRC holders.
Has Strategy ever sold Bitcoin before?
Strategy disclosed its first Bitcoin sale since 2022 in early June 2025, breaking a long-standing policy of accumulating and never selling. Michael Saylor, the company's executive chairman, had built Strategy's brand around that no-sell commitment.
Where Things Stand
Strategy's situation reflects how quickly crypto cycle sentiment can reverse. Shares that topped $400 just months ago are now trading below $100, preferred shares meant to be stable are down sharply, and Bitcoin's own correction from its record high has erased more than half its peak value. The company's next moves, whether more buying, more selling, or a shift in capital strategy, will be watched closely by anyone with exposure to the Bitcoin treasury model.
