🥛 Will Saylor have to sell his BTC? 😬

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Here’s what we’ve got for you today:

✍️ Will Saylor have to sell his BTC?
🎙️ The Milk Road Show: Bitcoin Sentiment Is the Worst Ever - But James Lavish Sees $500,000 by 2029.
🍪 1M+ Gram wallets activated in 48 hours.

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Prices as of 2:00 p.m. ET. Powered by CoinGecko.

MSCI JUST KICKED SAYLOR OUT 🚪

Last night, Michael Saylor's Strategy (aka: the biggest corporate holder of bitcoin) got some bad news that it spent a year fighting to stop from being delivered.

MSCI, the company behind a handful of stock indexes that trillions of dollars in index funds copy, is removing Strategy from the MSCI USA Index, which also boots it from the bigger MSCI World and ACWI (its all-country index).

In MSCI's view, Strategy looks more like a fund that holds Bitcoin than a company that runs a business.

Ok… where’s the fire?

Funds that track an MSCI index have to own whatever's in it, so this removal cancels out a whole lot of automatic buy pressure for Strategy stock.

Companies tracking MSCI’s indexes now have until Nov. 30 to sell their MSTR shares.

Silver lining: Strategy says those funds hold ~13M shares (about 3.1% of its stock), which is less than a single day of MSTR trading volume.

This fight has been dragging on for a while now…

MSCI first floated booting crypto treasury companies in October 2025, backed off in January, then came back last month with a broader test for "non-operating" companies.

Strategy failed it, after calling the rules "discriminatory, arbitrary, and misguided" in a letter to MSCI.

In that time, the stock has been sliding, though it looks to be correlated to BTC’s price more than anything.

Since MSCI's first proposal, MSTR is down ~62% while bitcoin is down ~39%. 👇

Source: Digrin, StatMuse, MarketBeat

Last night's news knocked off another chunk, with MSTR closing Wednesday at $122.35 and trading ~6% lower this morning (~$115).

Bitcoin barely flinched, slipping from $74.8K to ~$73.3K overnight (with Nvidia's after-hours drop landing at the same time).

Thankfully, getting booted doesn't force Strategy to sell a single Bitcoin…

But it does hit the machine Strategy uses to buy them.

THE NEXT BIG TRADE IS COMING

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MSCI JUST KICKED SAYLOR OUT (P2) 🚪

Strategy buys Bitcoin by selling new MSTR shares and preferred stock (shares that pay a fixed dividend).

That machine runs best when MSTR trades at a big premium to the Bitcoin behind it, because each new share sold raises enough cash to add Bitcoin per share for everyone else.

The premium gets measured with mNAV (Strategy's total value, counting its debt and preferred stock, divided by the value of its Bitcoin).

And that premium has mostly disappeared: 👇

Source: Strategy, CoinDesk, The Block

In November 2024, investors paid $3.40 for every $1 of Strategy's Bitcoin.

Today they pay ~$1.08, and in June it dipped below $1 for the first time.

Near 1x, selling new shares barely adds any Bitcoin per share (and below 1x, it shrinks it).

Last week, Strategy raised $283.8M selling MSTR shares and put just $81.9M of it into Bitcoin.

Now add the index exit on top:

Those ~13M shares were worth ~$1.57B at Tuesday's close.
JPMorgan estimated MSCI's exit alone could drive up to $2.8B of selling.
That jumps to $8.8B if other index providers copy MSCI.

BloFin Research thinks losing that index demand could shrink the premium further and slow Strategy's Bitcoin buying.

But before you panic about BTC:

The sale has a known date and a rough size, so traders can get ahead of it, and Markus Thielen (founder of 10x Research) thinks most of it is reflected in MSTR's price by now.

Strategy also isn't the buyer moving Bitcoin anymore.

It bought 1,036 BTC last week, while investors pulled roughly 4x that much out of U.S. Bitcoin ETFs on Wednesday alone.

The worst case is a premium stuck below 1x with no other funding, and CEO Phong Le said last December that Strategy would consider selling Bitcoin if that were to happen.

We're not there yet, but it's the scenario to keep an eye on.

Here's what we're watching next:

Strategy's buy update on Monday (does the buying keep going?).
The Nov. 30 close, when the index funds have to sell.
Whether FTSE Russell or S&P copy MSCI (the $8.8B scenario).

Keep your eyes peeled!

P.S. John (our crypto analyst) has his BTC buy zone at $71-72K, only ~$1-2K below where it trades now.

Try Milk Road PRO for $1 for 7 days to see the moment he makes his move.

THE REAL MELTING ICE CUBE

Bitcoin is stuck in the low $70Ks, inflation is back near 4%, and the Fed looks set to hike again in December.

James Lavish, co-managing partner of the Bitcoin Opportunity Fund and author of The Informationist, joined John to explain why none of it changes the endgame.

Here's what we covered: