Key Takeaways
- Peter Schiff attacked Strategy’s STRC buybacks as the company disclosed another $188.3 million in repurchases.
- Tonight’s MSCI review could remove Strategy from stock indexes, potentially weakening demand for MSTR shares.
- An older JPMorgan estimate put possible MSCI-related selling at $2.8 billion; removal would not automatically force Bitcoin sales.
Michael Saylor’s Strategy is currently facing pressure from gold advocate Peter Schiff, who questions the cost of supporting its preferred stock, as well as a looming decision on whether to remove its common shares from major stock indexes.
The Bitcoin critic called Strategy’s STRC preferred stock “dead” as the company disclosed another $188.3 million in repurchases, more than twice its latest Bitcoin purchase.
Separately, Saylor’s Strategy faces possible removal tonight from MSCI’s Global Investable Market Indexes under new rules covering companies that primarily hold investments.
If Strategy is excluded from the index, could demand for the shares funding its Bitcoin strategy weaken just as it spends heavily supporting another financing product?
Schiff Attacks Strategy’s STRC Buybacks
In a Nov. 9 X post, Schiff accused Saylor of keeping STRC afloat through repurchases.
“Michael, STRC is dead. You have been keeping it alive on artificial life support with your buybacks,” he wrote.
Schiff argued that further Bitcoin losses would increase selling pressure on STRC and questioned whether its income payments adequately compensated investors for the risk.
Schiff added that “as Bitcoin crashes,” the selling pressure on STRC will continue to grow.
“A 12% yield won’t be nearly enough to offset the risk,” he added.
Saylor’s Strategy Spends More Supporting STRC Than Buying Bitcoin
Strategy’s Nov. 9 filing shows it raised $283.8 million from selling MSTR common shares during Nov. 2–8.
It directed $188.3 million toward STRC repurchases, $81.9 million toward Bitcoin and $13.6 million toward USD Cash.
Around 66% of those proceeds went to buybacks, compared with 29% for Bitcoin.
The purchase added 1,036 BTC, bringing its holdings to 850,364 BTC.
This allocation links Schiff’s criticism to tonight’s index decision.
Strategy is selling common shares both to accumulate Bitcoin and to repurchase preferred shares; a possible reduction in demand for MSTR could make that balancing act harder.
Why Tonight’s Stock Index Decision Matters
MSCI runs stock indexes that investment funds follow. If Strategy is removed, funds tracking those indexes would generally need to sell its shares.
The provider plans to publish its November review shortly after 10 p.m. London time on Nov. 11.
Under rules adopted Oct. 15, companies that mainly hold investments could lose their place.
MSCI checks their assets and finances, with existing members generally needing to fail its tests for two consecutive annual reporting periods before removal.
Could Removal Trigger $2.8 Billion in Selling?
JPMorgan previously estimated that exclusion from MSCI indexes could generate approximately $2.8 billion in outflows from Strategy shares, according to its November 2025 research.
The practical risk is that index-linked selling pressures MSTR and makes future fundraising less attractive.
At a lower share price, Strategy would need to issue more shares to raise the same amount of money.
However, in its Oct. 29 results, CEO Phong Le offered a more positive assessment:
“Strategy demonstrated its commitment to returning STRC to health.” strategy.com
As of Oct. 25, the company reported $2.04 billion in cumulative STRC repurchases and $5.07 billion in USD Assets, describing around 3.4 years of dividend and interest coverage.
The same release disclosed around $431.8 million in Bitcoin sales in 2026 to fund part of its preferred dividends and STRC buybacks.
Its newer filing reported a $4.77 billion USD Reserve and $146.2 million in separate USD Cash as of Nov. 8.
Saylor Previously Faced Backlash Over ‘Never Sell’ Message
Schiff’s latest criticism follows an earlier dispute over whether Saylor’s public messaging about Bitcoin aligned with Strategy’s corporate actions.
After Strategy sold 1,638 BTC between July 27 and Aug. 2, Saylor sought to distinguish his personal holdings from the company’s treasury.
“When I say ‘Never Sell Your Bitcoin,’ I speak as one saver to another. I have never sold mine. Not one satoshi,” he wrote on X.
Saylor said Strategy needed flexibility to manage its finances.
“Strategy is a public company, not my wallet. Since 2020, it has disclosed it may buy or sell BTC to manage capital. Our shared conviction in Bitcoin remains unchanged.”
Although the transaction represented around 0.2% of its previous Bitcoin holdings, it drew scrutiny because Saylor had become closely associated with an uncompromising buy-and-hold message.
Schiff Challenges the Distinction Between Saylor and Strategy
At the time, Schiff rejected Saylor’s explanation, accusing him of allowing investors to believe the company would never sell Bitcoin.
“Yes, but you knew the impression you were creating, and you never bothered to clarify it,” Schiff wrote.
Other critics circulated an older clip in which Saylor described Strategy as being “in the business of buying Bitcoin” and said:
“We’ve said we would not be selling any Bitcoin. Ever.”
Supporters defended the distinction between an individual investor’s convictions and a public company’s financing needs. Bitcoin Archive wrote:
“We know. Every Bitcoiner with two functioning brain cells understands this.”
The information provided in this article is for informational purposes only. It is not intended to be, nor should it be construed as, financial advice. We do not make any warranties regarding the completeness, reliability, or accuracy of this information. All investments involve risk, and past performance does not guarantee future results. We recommend consulting a financial advisor before making any investment decisions.
Kurt Robson is a London-based reporter at CCN, specialising in the fast-moving worlds of crypto and emerging technology. He began his career covering local news in Cornwall after graduating from Falmouth University with First Class Honours in Journalism. There, he cut his teeth on everything from council meetings to missing swans.
He quickly rose through the ranks to become a frontline journalist at several of the UK’s leading national newspapers. Over the years, he has interviewed musicians and celebrities, reported from courtrooms and crime scenes, and secured multiple front-page exclusives.
Following the upheaval of the COVID-19 pandemic, Kurt shifted his focus to technology journalism—just ahead of the AI boom. With a natural curiosity and a trained eye for emerging trends, he has found a new rhythm in reporting on innovation.
At CCN, Kurt's work focuses on the cutting edge of crypto, blockchain, AI, and the evolving digital world. Drawing on his background in people-first reporting and his deep interest in disruptive tech, Kurt delivers stories that are insightful, entertaining, and human-centric.
