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THE BRIEFING
GM. This is The Crossover.
The man who has bought more Bitcoin than anyone alive is now the one everyone watches for a sell button.
BITCOIN · Desk

Strategy's Bitcoin machine is starting to creak.

Michael Saylor built the most famous Bitcoin bet on Wall Street. This week it began to creak.

His company, Strategy, is one giant tank of Bitcoin. It runs on three parts that prop each other up: the Bitcoin it holds, its own shares (ticker MSTR), and a row of preferred shares. There are four of those (STRK, STRF, STRD and STRC), and STRC alone pays an 11.5% cash dividend.

All three gave way at once.

MSTR fell below $100 for the first time since March 2024. STRC dropped to about $80, well under the $100 it's meant to be worth. Bitcoin itself slipped below $60,000.

Here's how it works. When MSTR is high, Strategy sells a few shares and buys more Bitcoin, and the high price makes that cheap.

When MSTR is low, the same move turns dear. To raise the same cash it must print far more stock, dragging the shares lower still.

And the dividend bill keeps growing. It has swollen from about $300 million a year in January to $1.2 billion now. The cash to cover it has shrunk from seven years of room to roughly fourteen months. CryptoQuant reckons Strategy needs around $2.8 billion to build the cushion back.

That leaves one real way out. Sell Bitcoin. And that's the trap.

Strategy already sold a tiny 32 coins on 1 June to cover a dividend payment. Against its 840,000-plus hoard, it was nothing.

But the market saw it, and MSTR is down about 38% since. The whole promise was that this pile never gets touched.

Not everyone's worried. Analyst Fred Krueger notes Strategy still sits on roughly $32 billion in spare cash, and nobody's forcing it to sell. True enough, today.

But the steadiest big buyer Bitcoin has is now the name everyone watches for a sell button. If Saylor ever has to press it, the weight comes down on all of us.

MACRO · Desk

One number on Friday decides everything.

At half past eight on Friday morning, the US government puts out its inflation report for May. It's the gauge the Fed watches most, called PCE. One number, and the whole market is waiting on it.

The guess isn't pretty. Core prices are tipped to run at 3.4% over the past year, the hottest since 2023.

The new Fed chair, Kevin Warsh, has already said he's in no rush to cut. Traders now put the odds of a rate rise in September near 68%, up from 29% a week ago. High rates keep the dollar strong, and a strong dollar has kept a lid on Bitcoin all month.

One thing pulls the other way. Oil has fallen back to pre-conflict levels, which should cool prices later.

A hot number on Friday locks the ceiling in place. A cool one is the first real opening crypto has had in months.

STABLECOINS · Desk

Crypto's rails went global this week.

While the price drifted, the plumbing went global. Ripple's dollar stablecoin RLUSD opened in Japan, waved through by the local regulator. It's the first time the token has set up shop in a big market outside the US and Europe.

A few days before, Coinbase won a single licence in Luxembourg that lets it work across all 27 European Union countries at once, and its boss hinted more buyouts are coming.

Add in American regulators clearing crypto-style perpetual futures for US exchanges, and Wall Street firms putting real shares onto blockchains, and the pattern is hard to miss. The people laying crypto's pipes are speeding up, not slowing down, even as the tokens sag.

If you're holding through the grey, that's the part worth holding onto. The tokens sag on the screen in front of you. The pipes underneath them keep getting laid, week after week.

🎲   The Odds
Will Bitcoin dip to $40,000 by year-end?30%
  
+2 PTS  ·  Three in ten now bet Bitcoin slides the whole way to $40,000 by year-end, up a couple of points this week. With the funds selling and the big corporate buyers gone quiet, a drop that deep no longer looks daft to the crowd.
Will Solana dip to $50 by year-end?60%
  
FLAT  ·  Six in ten bet Solana drops to $50 before the year is out. A gloomy call for a chain that keeps signing real payment deals. The money is betting that use and price can keep pulling opposite ways.
Will Dogecoin climb back to $0.48 by year-end?8%
  
FLAT  ·  Fewer than one in ten think Dogecoin climbs back to $0.48 this year. The first meme coin of them all is priced as a long shot now, a sign the hot air has mostly leaked out.
👁   What to Watch
01Whether Trump signs the CBDC ban. Congress has sent the President a bill that bars the US government from making its own digital dollar (a 'central bank digital currency') until 2030. Crypto counts that a win, since it leaves the field to private stablecoins. His signature turns it into law. Watch for any veto or hold-up.
02Kalshi's court fight with Illinois. Kalshi, a federally regulated venue where people bet on real-world events, is taking Illinois to court over a new state law that tries to rein it in. It's the first shot in a state-by-state fight over whether prediction markets count as gambling. The ruling will shape where they're allowed to run.
03The CLARITY Act's Senate vote. CLARITY is the big bill that would finally set out who regulates what in US crypto, the clear rules the industry has wanted for years. Word is it's one sticking point away from a vote on the Senate floor. Pass it and it's the clearest win crypto gets all year. Stall it and everyone's back in limbo.
📟   The Tape
Bitcoin is hovering just under $60,000. Still about half off its October peak near $126,000, and under the rough $78,000 it now costs to mine a single coin. About one miner in five is now losing money on each one.
The past year of US Bitcoin ETF flows just turned negative. First time since 2023. Look back a full year and the buying that built this rally has flipped to selling. CryptoQuant's chief says demand from both spot and futures has 'weakened significantly.'
Gold slipped below $4,000 for the first time in 2026. The other big bet against inflation cooled off as the dollar firmed. Money is leaving the safe corner and the risky corner at once.
Another crypto bridge got drained of $2.28 million. The money was drained out through an old, retired Aztec contract. That's the second bridge scare in a fortnight. The building boom keeps a graveyard running beside it.
Fear & Greed: 12 — Extreme Fear, down 5. A few green days never lifted the mood. A reading this low has more often sat near bottoms than tops, though it can stay fearful for a long while.
Saylor built a machine that was never meant to sell, and Friday’s inflation number will help settle whether it has to.
— TC
This is The Crossover. We tell you what’s moving and why; what you do about it is yours alone to decide. We can read a balance sheet well enough. Guessing Saylor’s next move is well above our pay grade.
This is not financial advice. The Crossover is for information and education only, never a recommendation to buy or sell. Crypto is risky and you can lose money. Do your own research and take professional advice before you act.

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