Strategy sinks as bitcoin plunges — the announcement it’s buying more bitcoin is not helping matters

Monday morning, Michael Saylor’s Strategy — the largest corporate bitcoin holder — was down a whopping 9% at market open, and is down more than 11% as of 11:55 a.m. ET as bitcoin struggles as well. The company is down about 15% year to date. The overall crypto market is taking a beating after Friday’s Crypto Summit disappointed investors. CoinMarketCap’s “fear and greed” index is at 17, reflecting “extreme fear.”

This morning, Strategy announced it would issue up to $21 billion of “perpetual strike preferred stock” to buy more bitcoin and “for working capital,” according to a press release.

Strategy has long been on a bitcoin buying spree, now holding 499,096 bitcoin. This places the company way ahead of the second-largest bitcoin holder, Mara Holdings, which holds 45,659 bitcoin in its reserve.

More Crypto

See all Crypto

Yaël Bizouati-Kennedy

12/10/25

Bitcoin rebounds but FOMC will set tone for Santa rally

Sage D. Young12/9/25

New bitcoin AfterDark ETF will be bitcoin at night, Treasurys by day

Tidal Trust II submitted form N-1A with the SEC to register a bitcoin ETF designed to systemically capture the cryptocurrency’s overnight return profile, a time window that delivered a significant portion of bitcoin’s upside last year.

The Nicholas Bitcoin and Treasuries AfterDark ETF provides long bitcoin exposure during US overnight hours, from the closing bell until the following morning’s market open, when the fund intends to unwind its positions, according to a document filed with the SEC on Tuesday.

To gain that exposure, the ETF may use a number of methods, including bitcoin futures contracts, US-listed ETFs, or exchange-traded options on such bitcoin underlying funds. When the market is open and daytime trading is active, the fund’s portfolio will consist of US Treasury securities and other cash equivalents.

In 2024, most of bitcoin’s gains occurred after-hours, senior Bloomberg ETF analyst Eric Balchunas reported:

We looked at this last year and found most of the gains are in fact after hours. Doesn't mean the ETFs aren't having impact. Some of this is positioning bc of the ETFs etc or derivatives based on flows etc etc. But yeah, bitcoin After Dark ETF could put up better reutrns, we'll… pic.twitter.com/BTpV51cQfl
— Eric Balchunas (@EricBalchunas) December 9, 2025

The AfterDark ETF filing comes as bitcoin crossed $94,000 on Tuesday, rising 4.5% in the last 24 hours. Even though spot bitcoin ETFs saw nearly $60.5 million in outflows on Monday, the investment vehicles have a cumulative net inflow of $57.6 billion, per SoSoValue.

Yaël Bizouati-Kennedy

12/8/25

Bitcoin will “snapback or chop ahead of the Fed” decision

Traders on prediction markets are divided, giving an equal chance that bitcoin drops below $80,000 or rises above $100,000 this year.

Yaël Bizouati-Kennedy

12/2/25

Legendary short seller James Chanos on the problem with Strategy’s business model

The noise has grown louder about Strategy being in trouble, but most experts think Strategy can weather the current bitcoin downturn, though one critic predicts this is “the beginning of the end.”

Bitcoin Conference Draws Cryptocurrency Fans To Miami

Sage D. Young

12/1/25

Ethereum spot ETFs post highest monthly outflow of $1.4 billion in November, breaking seven-month streak

Meanwhile, ethereum developers are preparing for the activation of Fusaka, the next network upgrade.

Latest Stories

Sherwood Media, LLC produces fresh and unique perspectives on topical financial news and is a fully owned subsidiary of Robinhood Markets, Inc., and any views expressed here do not necessarily reflect the views of any other Robinhood affiliate, including Robinhood Markets, Inc., Robinhood Financial LLC, Robinhood Securities, LLC, Robinhood Crypto, LLC, or Robinhood Money, LLC.