The Wolf Of All Streets - Bitcoin CRASHES Below $58K As Saylor's MSTR Hits A 28-Month Low

Episode Date: June 26, 2026

Bitcoin just hit its lowest level since October 2024 — dipping as low as $58,000 with US spot Bitcoin ETFs seeing RECORD investor flight. The bear catalysts are stacking faster than any point this cycle: Saylor's Strategy just hit a 2-year low (-46% in 30 days), STRC briefly cratered to $74 (designed for $100), the company has only ~10 months of dividend coverage left with $1.2B in annual obligations, and Rosen Law Firm just launched a class action probe — with Saylor responding only that "volatility tests every capital structure." Add Binance LEAVING the EU after failing MiCA (France, Italy, Poland, Spain), the Nasdaq losing $1 TRILLION in 27 minutes today with no headline trigger, BitGo laying off 15% of staff, and the CLARITY Act at real risk of slipping to fall. But the bull signals are quietly stacking: US households are sitting on $3.2 TRILLION in cash (record high), Tom Lee's BitMine just joined the Russell 1000, SBI is acquiring Japan's largest crypto exchange, and Kalshi is targeting a $40 BILLION valuation. We break down whether this October 2024 echo marks the cycle bottom or the next leg lower. Learn more about your ad choices. Visit megaphone.fm/adchoices

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free of charge. BetMGM operates pursuant to an operating agreement with Eye Gaming, Ontario. Bitcoin crashes below 5,000. 58,000 American dollars as Sailor's micro-strategy under major pressure hitting a 28-month low. Bears are euphoric. I'm going to show you how bearish people actually are by taking a quick look at the prediction markets on higher prices for this year. And Sailor haters have also been whipped into a euphoric frenzy. I get the sentiment, but there are also some facts worth discussing. It's Friday, which means we're just going to riff, guys. Let's go.

Good morning, everybody. Welcome to Friday on the Hellscape. That is the crypto and Bitcoin market. Bitcoin, you know, back to prices from years ago. It's like you got really excited about buying the Bitcoin highs in the last cycle and you're actually down if you've been holding now for years. All coins look like they're absolutely dead. There's LeCroy awkwardly in the volcano. Oh, if they don't literally like, oh, it's moved.

First of all, the smoke's moving. Did you make the smoke move? Or is that my eyes? You made it move. And it's moving in. I think it's sucking into the volcano. But if I was going to do a, if I was going to do a LeCroyad, I would have a LeCroy Volcano.

Sweet. Okay. What was I talking about? All right. I don't remember, to be honest. So we're going to start again. I'm very easily distracted. It's Friday and the ADD hits different.

So, you know, we're going to go ahead and just start kind of with the Bitcoin chart and price and show you why bears are an exploding volcano of excitement. I did the wrong one. Look at that. There is. Take a look at the chart. This is the weekly Bitcoin chart. Many rightfully pointing out that we are trading at the lowest point since October 24.

Not much bounce to the ounce right now. And trading currently below the 200 M.A. we will see what happens by the end of the week, which is Sunday, right? Not very long. We got about 24 times 2 plus 12, 60 hours until the week closes and we see if we get this closed. Now, we've only had this really happen a few times in history, most notably FTX, right? You can zoom back on the weekly chart here. Every other time we've touched this red line, that's the 200 M.A.

We've basically bounced. We closed slightly below it once in a previous cycle, but we're immediately back above. FTX it broke below on the first try, though, a little different. And traded below basically for nine months and kind of broke below a little bit here. Starting to look likely that we might lose the 200 M.A., which is giving bears

a little more excitement about prices going much lower. Now, if you're a person like me who actually likes buying Bitcoin, it doesn't really bother me. I'm going to be really super honest. We kind of joke in our studio all the time that we'd love to buy Bitcoin at like $50,000, $45,000.

I don't know. But the problem is that there are some systemic and sentiment risks to prices going lower, and we have to be intellectually honest about that. But I took a look. So as you guys know, like we partnered with Kalshi a while ago. I did that video, which was really cool on their perpetual swap product, which I think is great with extremely low leverage. So now I've been, you know, I can actually trade on Kalshi

and I can't on polymarketers. I've been taking a look at their markets. How high will Bitcoin get this year? Only 15% of people here thinking above 99. So we have six months left. Like anyone who's been here knows Bitcoin can double or half in price literally, immediately. I mean, March 12th, 2020, the COVID scare, Bitcoin price cut in half and bounced all the way back in 12 hours, basically. It went from, you know, just above six to 30.

I called a 45% drydown and bounce right back all in a matter of 12 hours. So, you know, above 110, 18, above 1209%. Now we're starting to get into the crackheads. 8.3. I made above 199,000. 4% of you out there. I don't know. I would take the other side of that one in theory, but like there were people who also bet like a million dollars to make 30,000 on Spain beating Cape Verde and lost a million So that that 4% sure thing in prediction markets, never a short thing. But I found this one really interesting.

Actually, like you, Bitcoin price at the end of 2026. 19K or below. I mean 20K or below. Wow. 4.5. Interesting. So listen, these are spread out in $5,000 buckets. But you can see that the big interest right now is basically anywhere from

69 down to, let's call it, 45, right? Even 75 down. Above that, there's not a single bet, really, above 70, that is even more than 4% than anybody would take that bucket. And you start to get up into the hundreds, and it's like 3%, 2%, 2%, 2.8%. So I would say that consensus very clearly, when you look at these markets, is that there's basically no chance we get back above 75 to end the year. Six months, five months, six months away. Math. Six months away.

Somebody said, has Scott defended STRC yet today? No, I'm going to get there. Don't worry about it. The funny thing is, should we do Sailor now? Yeah, we'll do Sailor now. Let me see if I have any sailor images I can show you. because this, so here's my problem.

I have a problem. Okay. It's buying Bitcoin, no matter what price it is. But I have another problem. And it's that I'm being viewed as like Michael Saler Homer at this point. And I do, you know, I am friendly with him. And I deeply and genuinely appreciate how much buying he's done for Bitcoin and what he's built over the years. And I think we obviously wouldn't be anywhere.

near where we are without him. There's a flip side to that, which is that there's people who are so far down the bearish rabbit hole of him that there are irrational arguments. And my issue is when I see irrational or factually incorrect arguments on social media, some like instinct in me jumps in where I have to correct it. And there's so many bad, unfactual takes on strategy and sailor right now that I keep jumping in to clarify them and it looks like I'm massively defending him. I'll be honest, I don't own, like, I had bought some micro strategy, I think at 150 or something. It went up to 170 and it dropped, it hit my stop. I'm out. I do own STRC. I bought some at 100. I bought some in the low 90s. I will buy some more here. But it's a very small fraction of my position

that I view literally as the dividend and I don't see the dividend going away. In fact, I see it going up. So as long as they continue to pay the dividend, the price of it is really irrelevant. Right. So listen, I don't think that STRC going down is good. It's obviously a bad signal of confidence in the market, but I think that there's a lot of reasons that confidence is down that are false. Right. So that's kind of the problem here. It's funny.

There's an article here on Yahoo Finance, which they always put my face on. They just run the Daily Wolf in all the Yahoo Finance articles. I didn't write the article, and it looks like I said, Michael Saylor's strategy faces no easy way out as Bitcoin prices continue to drop. That is somewhat true. And then I want to get into this law firm. But so, like, I think where people are conflating this on social media is there are people who think it's in a death spiral and it's over.

And there's a very major difference between no choices or and no great choices. Right. I would say right now in the very short term, he doesn't have great choices. He has to slightly dilute micro-stratory, shape. shareholders to be able to add back to the cash reserve and to be able to buy more Bitcoin. I can see an argument for saying, hey, stop buying Bitcoin for a while, bro. I see people saying that. That could be rational. I can definitely see an argument for them having not, they should have not paid off the convertible note for $1.3 billion because that sparked all of this because their cash reserve was big enough.

But they're adding back to that cash reserve every single week. So I can see all the negative arguments. but he has plenty of options that are slightly dilutive in the short term to shore up the balance sheet. He added $300 million to the cash reserve last week. They only have $1.8 billion, $1.7 billion a year in dividend requirements. They added 20% of that just last week, almost. Right? So I think it's very clear he's going to add to the cash reserve and shore that up. Will STRC trade back to par anytime soon?

I have no idea. Will they keep paying their dividend? Highly confident they will because that would be end times if they stopped doing that. So just to be clear, if you, no matter what price STRC is trading at, you get paid $11.5 bucks for every $100 on the year. That is at par to $100. Right. So yeah, right now I don't think he has an easy way out. And the funniest thing, though, let me say this. You know what the easy way out is that nobody is considering Bitcoin goes up. Like everyone who is super dooming sailor, and I get it. Like they've made it their whole personality. You know, you know how you get on social media and you feel like you're right about something and you keep pounding it. I get it. I get the emotional attachment there to being right. But that is also

an emotional attachment to there being no chance that Bitcoin goes up. So if Bitcoin's at 80K, we're not even having these conversations, right? Everything is good time. and puppy dogs and unicorns and, you know, I don't know. Something else that I was going to say that was going to be so wildly inappropriate that I once for once decided to stop myself. So, yeah, you look at that article there, and the next one was the one I wanted to get to. God, man, why can't people think?

Rosen Law launches, law firm launches, pro, probe into micro strategies. That is an accurate, that is an accurate headline. The inaccurate headlines I've seen are that Sailor and Strategy are being investigated. Some people have said SEC and DOJ probing. Some people saying class action suit filed. And any person in America knows that you can sue anybody for anything all the time where the most litigious society in the world and many would say that if you own a company, class action lawsuits are literally the cost of business. But here is one of those headlines. Strategies reportedly being investigated over the issuance of STRC, right? No, they're not being investigated. What we actually have is a law firm

using all of us, myself just included right there, as free PR to try to get people to join a potential class action to sue sailor. If you operate in crypto, and you're in my position or something, you probably are going to get sued or have been sued or somebody or named in a class action. Right. I was once named in a class action for Voyager, and it was like me,

Mark Cuban, Marshall Falk, Landon Cat, like all these celebrities and like my name was there at the end. It got dropped, right? But there's law firms out there like this one that literally sue everybody.

Like I was getting sued for something to do with FTCS and everybody. anything to do with FTX, but they looped them all in. Right? And nobody ended up getting paid. These law firms and their clients end up spending a whole ton of money, but I did have to pay for lawyers for like this insanity. Never talked about it, actually. But yeah, you know, I like the information you bring, but you were definitely pushing a bull market while market was clearly rolling over. Oh, if you want to fault me for having a broken crystal ball and a bad opinion. All day, bro. I'm a bull. I'm optimistic. I frame almost

everything optimistically. And at no point do I tell you with any certainty where anything is going in the future, I just show you when I buy stuff. So if you're mad at me that I bought Bitcoin at $88,000 and thought it might be a bottom, that's literally my money that I bought something with. So cool. You know, but so like, listen, we get these like nothing. I think the, overwhelming theme here is that you can't believe literally anything that crypto Twitter tells you. You just can't. It's all wrong. It's all wrong. What is right, though, is that like we're definitely in a bare market. You're right. And maybe I was against, I don't really believe the four year, that the last cycle looked anything like previous parts of the four year cycle, but this part certainly

does. So maybe I'm wrong about that too. I don't know. I'll know. I guess we'll see. Bitcoin ETFC record investor flight is a cryptocurrency hits lowest level since 2024. So like, Listen, every headline is bearish. Fear and Greed is through the freaking floor. And there's not much good news. Another story we've been tracking here. Wrong thing. That one.

Like my knee jerk is to hit the same button every single time. Binance says some European clients may be affected after pulling bid for Greek license. I don't know if you guys saw this story, but basically Mika is sneaking up on us. those rules they made many years ago. Well, July 1st is the deadline to get regulatory approval. OKX has it. Coinbase has it. Cracken has it.

Finance somehow was kind of choosing regulators. And Greece was supposed to be the easiest ones. They went to Greece and then had it on good information like a week ago that they were going to get rejected. Right. And then the story came out that it was Christine Lagarde herself, the head of the European Central Bank, who called Greek. It's like, bro, kick finance out. Right. And it's part of her war against stable coins, obviously.

But it's a pretty big deal. So they pulled their application in Greece. Like I said on the Daily Wolf yesterday, this was basically like Binance realizing that their girlfriend was going to break up with them and then breaking up with her first. You know? Because you don't want to be the one who gets broken up with. Like they knew they weren't going to get the license.

They pulled it. But now they're scrambling to find another regulator in the next four or five days to approve them. And if you get regulated in one, if you get approval, you're good for the entire European Union. Well, that not happening here. and so it could get pretty ugly here in the very short term. Sad to see EU cutting their users off from the best liquidity in the world. Quitty is the best consumer protection.

Hope to see things change in the future. Richard Tang basically said, hey, we'll get this in the next couple months. But also, you're going to probably get a lot of a two FAA and scam texts for people claiming that they're Binance and trying to solve your stuff. Five scary things that happen. J. Crypto. Exchange was its meekal license on July 1st.

But these are things if you're in the EU, you should probably think about now. Withdrawals can freeze before you expect them to. Your investor protections disappear immediately. Nobody believes they have investor protection. You may be forced to migrate to a platform you did not choose. Criminal liability falls on the exchange, not you, but you still pay the price. And your exchange may simply stop serving you with no warning.

My waitress did that the other day. How to protect your crypto before July 1st, do a bunch of stuff. Basically, I get your money off exchanges that might be kicked off. Very simple. But yeah, so that's not the greatest of stories that we've ever seen, unfortunately. But, you know, I would just be careful and choose wisely. Your exchange is moving forward if you are in the United States. Now, where's one more thing I want to talk about?

So we had, I want to talk about generally markets because I thought this was an interesting thread. Take a look at. Yesterday, obviously, when Bitcoin did make that move below 58, all markets were dumping. And a lot of people pointed at it being because, of PCE. So obviously, PCE is the Fed's preferred inflation gauge and does not include energy and it was up. So basically, inflation was the hottest. It's been in a long time, even if you discount energy. That said, oil prices are down so low that that is going to be disinflationary over the next

couple months and could counteract that. But obviously, markets reacted very negatively. But maybe the bigger story, as COBC points out here, and something that I noticed as well, was actually what happened with Apple. So Apple, if you didn't see this, raise prices on Macs and iPads by up to 25%. And Tim Cook said soaring chip costs made the hike unavoidable. This is the first big sign of what we're calling AI inflation. Inflation due to AI is being passed on to consumers.

So I think that might be the bigger story because even if energy is bringing inflation down over time, we have seen a hot inflation print. And when you add to that a 25% price hike from Apple, the biggest consumer goods company on planet Earth, it makes you wonder what's going to happen. You know, technology is supposed to be deflationary. I'm sure you've all read the price of tomorrow by Jeff Booth. If you hadn't, you should go read it. But generally, like, the price of your TV comes down over time because technology makes things cheaper. Right? Your iPhone, as he always points out, it's like, you know, you used to just have a phone and you had to have a camera. camera and then you have a calculator. These are all separate devices. Now, all those things are free inside one device. And it makes everything in life cheaper and the natural force of things if you get rid of monetary and fiscal policy is deflation. Well, what happens when there's so much

usage that chip costs continue to go up and that's unsustainable and everybody's prices of the goods that they use every single day continues to go up? So I do think that that is really, yeah, yeah. clone was right. Cry. He's been right about a lot of things. He was super early and I don't think he'll be right to the ultimate downside, but he has been very right for a long time. I remember that, I don't remember what the steak dinner was, but the first bet Dave crushed him in the steak dinner, higher price of Bitcoin or something. But if you remember at the peak, I think, of the Bitcoin gold ratio, they made a bet in a year, which one, if that ratio would be up or down and it was down bad. Gold absolutely crushed Bitcoin in that phase. You got to give credit where it's

you guys. You got to give credit where it's due. And there's a lot of credit, even to the bears, for being correct. Yes. Now I'm looking at what you guys are saying. Friday monologues, the best show of the week. You can just watch me do this on Yahoo every day. Not this, though. I don't drink there. I don't drink at work. This flavor is pretty good. Kee lime. It's naturally essenced. It's not great, but it is more flavorful than some of the other ones. But key lime, you kind of think of dessert, and this does not taste like dessert. More like something you would drink in a dessert.

But you ever get the spelling of those wrong? You know how I remember it. Desert is the one you don't want desert. You want dessert. It's got more S's. Someone taught me that one. Yeah, Fridays are fun because you can show up. I don't have to stress about my guests.

and whatever. Speaking of which, I thought the guests this week were amazing. I don't know if you guys thought that, but we had obviously Brent, Sontow and Capital, literally the guy who created the dollar milkshake theory that has been quoted in economics for years. We had him on Monday. Guess who's going to be here Monday?

Guess who's joining? Okay, I want you to take your guesses who's going to be the fourth since James isn't there for Macro Monday on Monday. But then on Tuesday, we had Caitlin Long, who was amazing. Then on Wednesday at Dan Gunsberg, I thought he gave great, great insight on options and prediction markets. Then yesterday, Ryan from Bitwise was an absolute rock star. People were pointing out that my volcano's imploding.

I talked about that already. I admitted it. Ah, yeah, sailor, not sailor. Larry coming back, someone said, Superman, no. Larry coming back, I invited him. And he said he couldn't do it. did invite him. I literally invited Larry. So yeah, let me see. Larry coming back. No. Who do you guys think?

Larry the part? No. It's not Larry. You guys aren't guessing enough. I'm going to tell you. I don't know if there's a good for you. One Peter Schiff, Esquire. One Peter. Big Peter Schiff. Peter Schiff. Can you imagine Dave Weisberger's brain while sitting across the screen

from Mike McLaughone and Peter Schiff at the same time? Can you? Can you? Me and Dave, we're going to be doing the ADHD uncomfortable dance the entire time. Peter Schiff. Peter Schiff will be here on Monday for Macro Monday. It's going to be epic.

Come on, guys. And people actually, you know, They get mad that, like, I tweet Peter Schiffisms and stuff. But guys, you know, it's hard to be balanced in this. And I say, and I take the most retardedly bullish things and tweet about them. Tom Lee says Ethereum will be $475,000 by last week. Nobody gets mad at me for that. But I'm like, Peter Schiff says you're all investing in a Ponzi scheme.

For some reason, they get mad. Yeah, man, you know, I try. It's very hard. I learned very hard way in the past that being like a gratuitous bull all the time, or at least even if I am presenting only gratuitously bullish stuff, it's not good. Right? So listen, I like to have conversations with people like Peter. And let's be honest, he's going to talk about Bitcoin relentlessly no matter what

because, like, you cannot stop him. Last time I interviewed him, I started the interview with, Peter, we're not going to talk about Bitcoin because we agree on 99.9% of things, Bitcoiners, gold bugs, whatever. proceeded to just pound Bitcoin for like an hour, no matter what I asked him. But if we can actually focus on the macro, his perspectives are incredible and perfect in this, I think, economic times. I think it would be really, really, really, really good. Yeah. Will Peter be wearing a new gold girl? Actually, last time I was Peter and James Heckman, and you guys may remember, I started the show like this, and while the music was playing, I went and put on a bunch of gold chains.

And I said to Peter, I wanted you to feel comfortable here. You know? One of you. Anyways. So it's going to be a lot of fun. Someone said I would pay a lot of books for Larry to come back, tell someone else to fuck themselves. Well, he's, you know, I tried. I asked him, I was like, hey, I know you're not interested in this.

But do you want to come on a show in Mike McLaughone and Peter Schiff? Said no. You know, guys, you got to shoot your shot in life, you know? even if Larry was that hot girl at the bar and you knew she was probably going to say no, what if she said yes? Could be her future wife. Literally never know. I think it's going to be interesting.

I think the bulls might be outgunned on Monday. Could get real weird. All right. I just did this till 925. We covered all the news. The only other news I would say, wait, this is kind of important, I think. Fund Strats bit mine to join the Russell 1000 index after. market today. So I just find this very entertaining because all those retirees and people who have,

you know, 401ks and stuff who hate us, you all own Ethereum now. Congratulations, your favorite assets. I think I'm going to go ahead and leave. My head's getting hot. This ear is hot. This year, not so much. I don't know why. Yeah, it's pretty much all we got. I'm glad you guys stuck with me. It's fun. I really hope that you read the price of tomorrow. Someone just said, look at, oh, that's not what I was looking at. That's not what I read. My eyes don't work. But God bless the saints who found their wife at the bar. Found my wife at a bar. Club. It was a simpler time, you know, when you talked to girls. with your mouth. Crazy man. That's all I got today. I will see you. Show up at noon for the

Daily Wolf and otherwise like just go use your pencils or your fingers or whatever you're going to do to put in your calendar that shifts joining on Monday. It's going to be epic.