The Wolf Of All Streets - Bitcoin Bull Saylor To DUMP $30M Today?

Episode Date: May 29, 2026

Bitcoin just cratered to a six week low below $73,000 as fresh U.S. airstrikes on Iran reignited Strait of Hormuz war fears, triggering $897 million in long liquidations and the second largest daily IBIT outflow on record at $528 million. The pain is everywhere right now. Fund manager Michael Kramer is warning a $150 billion Treasury liquidity drain over the next week could send BTC much lower, while CME finally killed the famous weekend gap by launching 24/7 futures trading. Meanwhile, Iran is calling negotiations a strategic deadlock, the CFTC made a stunning admission that the Gemini case never should have been filed, the FBI just seized a record $8 billion in Bitcoin from a Cambodian scam compound, and Paxos became the first blockchain native firm approved by the SEC to clear and settle U.S. securities on chain. Plus a single enterprise client racked up a $500 million Claude bill in 30 days with no usage limits. We are breaking down whether Bitcoin defends $72K or rolls over to new lows, what the Hormuz escalation means for risk assets, and why this could be the most consequential 24 hours of the entire cycle. Learn more about your ad choices. Visit megaphone.fm/adchoices

Is Bitcoin Bull Michael Saylor going to dump 30 million in Bitcoin today? Strategy sent 411 Bitcoin over to Coinbase Prime. It does not mean they're going to sell. But considering he said that it was going to become part of their strategy and that he was going to inoculate the market by selling some Bitcoin, this could be the day that the never-sell mantra finally dies. We've got that. And a lot more today as I rant solo here on a Friday.

Let's go. Good morning, everybody. Welcome to the Wolf of All Streets here every day at 9 a.m. Eastern Standard Time for your viewing and listening pleasure, basically an orgasm for your eyes and your ears. Now, before we get started, I would like for you to like and subscribe to the channel. You might not know this, but I just did a deep competitor dive on YouTube. And while other channels die, we are marginally growing. And it's something to be really proud of. We have new subscribers, other people are losing them. Our views are up like six. Other people are down like 6,000.

Feels good to be the best. That's all I'm saying. But you know what is not the best? And I'm going to be honest. I'm having a really bad day. And the reason is because we only had two LaCroix left in the fridge. And you may remember from LaCroix comments of the past that Limoncello is the absolute worst flavor that's ever existed.

I'm sorry, LaCroi. I don't want to lose my sponsorship. But I have to be honest. I've grown a reputation of being honest with my audience. And this tastes like lemon pledge. In fact, I would argue that it would be more pleasurable to go into the bathroom of this office building and lick the floor right after they've cleaned it than to drink this absolutely disgusting concoction made by some Frankenstein monster. But you know what? It's become my gimmick and I'm going to just drink it.

The other problem here at my lakeside villa in Japan is that I forgot to wear my contact lenses today. So I can't see anything. To be honest, and reading the stories is very difficult. But we're going to dive into it right now because, I mean, it's like, how many minutes? We're three minutes in and I've told you nothing of any value. That's how we do it. All right, first story. Strategy moves 411.5 Bitcoin to Coinbase Prime.

On-chain data from Arkham shows strategy transferred 411.5 Bitcoin worth approximately $30.3 million to a Coinbase Prime wallet. Following the transfer prediction, markets increase the odds its strategy sells a portion of its Bitcoin by today 22%. While transfers to Coinbase Prime

often sparked speculation, they do not necessarily indicate an imminent sale. Yeah, we have no idea. They can move Bitcoin around for any reason. But listen, the guy literally told you he was going to do it. He has, I don't know,

you know, like almost a million Bitcoin at this. point, 800-something thousand more than I have, right? And he told you he's going to try selling some to inoculate the market. We've had Fongley, the head of strategy, the CEO of strategy, tell us the exact same thing, saying it's definitely one of the tools in their toolbox. And 411 Bitcoin is absolutely nothing. Right. So if what they're going to do here is sell a little bit of Bitcoin to make sure that the market sees that they'd be willing to do it to protect STRC and the dividends, I think that this is generally a good move.

I actually wrote a long newsletter today on why we vilify everyone who changes their opinion in crypto because I've seen people just absolutely trying to annihilate sailor of laid Vitalic Buterin is getting annihilated of late, Jack Dorsey, everybody, right? And why we say that we want people who are intellectually honest and then all of a sudden when they have strong opinions loosely held and they change their view based on new information why we continue to vilify them,

what that says about us versus them. Well, Michael Saylor is doing exactly what Michael Saylor has to do if he wants to continue to have the BitFack running. And I don't fault him for this at all. As I've said before, and in deep conversations with him and with others, STRC is a security.

And we can hate or love the SEC as much as we want, but the SEC takes investor protections very seriously. that is their actual job. And STRC cannot be promised to retirees with 11.5% yield and say it's backed by Bitcoin. And at the same time, have the person running that company say we would never sell that Bitcoin, because that is a absolute no-no. So they need to show the market. They'd be willing to sell it to protect this dividend.

And today, that's especially poignant and important because STRC, I did the wrong screen. suck. Muscle memory can't see. As strategies, SDRC slips below $99 as strive captures investor attention. SDRC struggled to maintain a $100 target price while strategies reduce cash reserves and dividend obligations are drawing increased investor attention. So actually, you know, after X dividend day, when the dividends are accounted for and paid, we always see SCRC dump from above $100 to down around 99. we've seen it go lower, obviously, and it went to a 97-11 today before bouncing up into the mid-98th

where it is right now. This isn't particularly abnormal for being honest. Oh, look, my screen's all messed up. Wait. Oh, that felt good. Looks good, too. It's great. It felt really good.

You guys are laughing and it's making me laugh. not you guys he's got and now they're dropping things um okay so i was talking about s jrc right okay so sDRC yeah obviously we've seen this behavior before it drops down and then you know slowly floats back up to par until it is on par and trading at a hundred well listen so like i said this isn't abnormal that we're seeing this but they're saying it's because strive is offering 12.5%, they're doing daily dividends, and maybe they've created a superior product by watching Sailor. I think also because they paid down that massive convertible note of late, that's making people scratch their heads because that wasn't due till 2029 and had a 0% coupon.

So like why pay off something with 0% debt and reduce your reserves from $2.2 billion down to, you know, 800 or 900 million, whatever it is. I don't have the exact number, meaning that they only have six months of runway instead of 18 months of runway for paying STRC dividends. I'm going to assume that they're not just making these decisions willy-nilly and it's going to be all fine.

But this is what the market is watching right now. And I think there's a very good chance they might sell some Bitcoin. It's possible. And I think it's fine. Sometimes you've got to do what you got to do. Like drink this garbage. It's really bad.

Lemon pledge. Honestly, I've never drank Pledge. I don't know. I should say if we're going to be accurate, taste how Pledge smells. That's what we got. In the meantime, Michael Saylor is not the only person who hates us. Bitcoin ETF Outflows reach record nine-day streak as investors full $2.8 billion. The longest run of withdrawal since U.S. spot Bitcoin ETF's listed in January,

2024 comes as Bitcoin underperforms high-flying AI and semiconductor stop. So I'm going to be the first gone on. Lemon say, fuck AI stocks and your semiconductors because you're making our lives hard and miserable. And that's bad. But yeah, I mean, this is, it's ugly out there, right? And I'm going to be honest, like Bitcoin just sitting here at, I would read the price, but my eyes don't work. $73,099. If we're seeing the most historic run of outflows is kind of a nothing burger.

I mean, 73, 74, 75, 76, it's just the middle of this range that we've been trading out since Bitcoin, bottom, and 60. If that's what our historic streaks look at, test me, bro. Bring me more. I think that that's not even a big deal. We saw the second largest daily outflow from Ibit ever yesterday or two days ago, over 500 million. But listen, like, I'm getting the text. You guys are getting them, too.

I can pull up an exact text. my friend who used to work somewhere that rhymes with Shittadel. He's now at a different firm, but let's just say that he's a, got more money than me. Holy shit, SPX outperforming Bitcoin in the last year by 60%. Three exclamation points. Wow. Yeah. I mean, listen, there's a lot of people out there who are not like deep.

So first of all, if you're a deep, deep, deep believer in Bitcoin, like global reserve currency, opt out of the system, interest rate, you know, interest inflation hedge, you're probably not like owning Ibit in size instead of spot Bitcoin. So you got to imagine the people who are owning Ibit who are reading the Bloomberg headlines and who are working at these Wall Street funds have that, right? Exactly this. It's like everything else is going up and your thing's going down. I showed that tweet yesterday. It was really funny. It was like Trump tweets about like semiconductors and yay, microns up 20%. Trump says that, you know,

the United States is the crypto capital world. We need to protect it at all costs. Like Bitcoin down 4%. Right. I don't know why we can't even get the Trump bump. I bet Trump does bumps. But I don't know why we don't get the Trump bump when every other market does.

But right now it's very clear that people are pretty aggressively running for the exits. There's an article on Bloomberg that I can't read, I told you. Right here. Bitcoin dips below 73,000, despite Trump's crypto capital push. I mean, this dude, I don't know if he's trying to talk the market up and it's failing, but Trump has been on like a heater sending out truths about the crypto market, right? Saying it will be the crypto capital world.

He did his like fire Gary Gensler thing. I'm not sure he knows that we fired him already. Seems confused. Have you seen like the memes the things going around where like there's some doctor who went on CNN? It's like Trump's dying and his dementia because his. knuckles are purple. Like, that's what's in the news now. Apparently, he has not slept in like 47 days or something, according to this doctor based on his knuckle photos. I know I'm the news, but like I don't actually report it. I just tell you things I think about what's in the news.

But yeah, I mean, this is the headline, right? Bitcoin dips below 70,000 despite Trump's crypto capital push. And Trump has been pushing as hard as he can. And it is not working, but it's working for every other market that we have. Pretty gross out there. Now, I have some really good news, and it's, if I can get the thing, it's this one right here. Bitcoin's famous CME gaps are about to disappear. The three remain unresolved. I know you thought the good news was going to be that my tongue is finally numb.

Still taste bad. Bitcoin's famous CME gap bout to disappear. The launch of round-the-clock Bitcoin futures trading eliminates the longstanding CME weekend gaps and marks another step toward fully integrated institutional crypto markets. I hate CME gaps. I hate waking up every Monday in my entire Twitter feed is traders who have probably never actually traded, but talk about it a lot on Twitter telling you that we need to fill the CME gap. Because if you don't remember, if you don't know what that is, Bitcoin trades 24-7, 365. So when you look at a Bitcoin chart, there's no gaps in it, right? There's no time when the

market was off. So the next candle starts where the last candle ended. Well, if you go, If that's happening on the weekend, but the CME is not open on the weekend, then if price started, ended Friday at 74,000 but opens Monday at 70, you have a gap of $4,000 in that chart. And nature abhors a vacuum. When you see gaps in stock charts, they tend to be filled. But you can't compare that to something that's actually trading 24-7, 365 somewhere else. But I'm so glad that I'd never have to hear about a CME gap again. I don't really care about the fact that the CME is doing the right thing. and, you know, going to go 24-7, 365.

I just care that I'm not going to have to look at these gap stories anymore. This one's cool. Taxos wins SEC approval to clear U.S. stocks on the blockchain. This is our first crypto-native clearinghouse that we get. They're going to be plugged right into the Wall Street system, DTC, all the things. And they've been fighting for this for a very long time. And Chuck Casperilla right there. Guys, awesome.

Taxos new license positions it alongside Legacy Giants, such as DTCC. It makes it a compelling, more efficient alternative for traditional finance giants than legacy competitors. That's coming from crypto media. So obviously we have a pretty favorable slant. But listen, we have no mysteries about the integration of crypto into the financial system.

This seems to be the topic of conversation on a lot of my daily wolves, but I went on Coin desk yesterday and they're asking me about this. We have this thing. There's Bitcoin and Bitcoin's fine. It's like the ETFs and institutional adoption and companies and countries and institutions or all buy it, whatever. But crypto itself, I think the most frustrating thing about being in crypto right now is that you have these sort of like two paths. Like one, we cheered for mainstream adoption. Blockchain is the best technology.

It's amazing. Everyone should use it. The problem is they started using it. None of our shit went up in value. Right? So we thought if they used it, all our beloved took, which hand is which? If we used it, all of our beloved tokens would go up and they just have it. Like, you can literally be like, you know, Elon Musk has decided that Chainlink will be the currency of planet Mars.

Chainlink, like down 3% on the day. What are we doing here? Stellar did go up yesterday on their DTCC news, though. So I think that that's nice. But yeah, so you have one path where they're basically using the technology, but they're going to do it in their own way in it becomes plumbing and it's boring and it's not investable. And then it's the other side where maybe we can build those systems or parallel systems. The problem is the parallel systems we've been building are getting hacked every day by North Korea. Right? I mean,

I don't, I don't, it's May 29th now, but I remember on May 19th, we had had 15 days with hacks in May. 15 out of 19 days. Something in Defi had been hacked. So I guess you can't blame Wall Street for wanting to create their own systems because it turns out that even though we hate them, maybe they're actually adults and we're a bunch of children. Possible. I'm 49 years old. Do I seem 49 to you? Child. Man child. Man child. Might go to a water park today. Man, 49. Cushing it. Went to a pump track the other day on my BMX bike. Not kidding. It actually happened. Hey, you want a story that's hilarious that has nothing to do with crypto? Me too. Client loses 500 million on Claude due to unclod due to unclothed.

capped AI usage. How do you pay that back? So, this is like an AI, it's an AI company, right? AI enterprise client racked up a half a billion dollar bill in a single month on Anthropics Cloud AI after nobody thought to set a spending limit. Okay, I have so many questions. This is on crypto briefing, so it counts. I don't even know if that's a real site. So FAA, like, Claude doesn't alert you like, your usage limits for the day or up. I guess they didn't send one. But usually I have some sort of usage of it. Nobody was like, hey, maybe I'll check mid-month on how much we're spending on Claude. Who has $500 million to spend in a month? This is like, you'd have to be like Apple or

Nvidia. Who is this person? And they're supposed to be apparently like an AI consultant that did this. I don't understand. Someone said here, wait, I heard the story. I so can't read. I heard this story might have been about meta. They require employees to meet an AI token limit. Okay, thanks, Drew. Good to see you, man. I remember that time that we shared your t-shirt store on here. That's cool.

Send it again if it's out there. Yeah. Somebody asked me, what's the latest on the peace deals? No, I'm not fucking CNN. Yeah, like I don't understand how this happened. it's just like a funny story. I can't even imagine. Like, we were talking about it before and you're like,

A, this guy gets fired, right? I mean, somebody gets fired. But B, it's like, I'll pay you back in monthly installments. $500 million. Ah, man, absolutely brutal. Hey, do you guys have anything you want to talk about? Show me in the comments and I will have to read them, I guess. Let me see if I can blow up my thing.

Somebody said, oh, it's AWS, something. that sounds bad for AWS. I can't read. 600 million to create who throwing monkey memes. That's a good comment. I couldn't read it until I brought it up. So now we're really winging it

because it's too small over there, but it's perfect here. I don't think they were doing that for the memes, to be honest. Can you address the fact that the entire market is... Oh, I can't read that one. that one's bad.

Because it says bad words, I can't say. Let's, what's this? Let's talk about the next narrative. AI tokens, all pumping, FET, render, I and J. Are they actually all pumping right now? I haven't looked, but I remember last time they all pumped on the AI narrative, and then they all went back down. So I think if you do these, like, narrative pump things,

Defi Summer, NFTs, Metaverse Fall. Remember when Facebook rebrands, to meta and all the metaverse things went up. That's disgusting. No, I don't believe in those. Because I think that tokens rebrand to be like the thing. I remember when all the layer ones became defy tokens. And now they're all going to become AI tokens.

And I do believe some of these will do well, by the way. But like I feel like you just get these narratives and things pump and then they inevitably drop down. It seems like hyperliquid is the strongest thing in the market. I don't own any because I'm ridiculous and dumb. But, you know, it's very actually easy to value that. And it seems to be outperforming every time we see a drop. Oh, before we dive into more things, our friend Chris, our friends over at BTQ, they had sent this. You might remember I had Chris Tam, the president of BTQ on the show recently.

And every once in a while, someone we've had on the show will send some news and be like, well, you share the news and share some news. BTQ Technologies completes acquisition of Q Perfect. They had announced this actually last year. expanding its quantum ready technology stack into software, emulation, digital twin, and control systems. This is my segue to talk about quantum, because it seems like that, speaking of narratives that come and go, we had quantum there for a very long time,

and this should still be a major narrative. I mean, basically what they did there is they added a massive software element to their stack, which was largely hardware. But this was just my segue to say that quantum is still very important, and it's something that needs to be discussed, and there are companies like BTQ, which is publicly traded out there that are working on this very, very actively on a day-to-day basis. But nobody's talking about quantum anymore. Do you find that weird?

Yes, we have other things to talk about, like aliens and more. Did you see it the White House teased an alien thing yesterday? And then did a like third grade animation afterwards, after they teased it of an illegal alien. They did like crop circles and stuff. It was like, oh, my God, we're finally getting an alien. And then it was like they lifted a guy who was like ambiguously Mexican over offense. Like this has to be a simulation, right? I've never been a theory of a fan of the like, hey, we're in a simulation theory because it just seems so minimizing to our humanity.

But man, some days it just feels like we're a son of it. Donald Trump Jr. married Jeffrey Epstein's private banker's daughter. And his dad didn't go. And his dad was like, known him a long time. He's a good guy, but I've got other things to do. It's a simulation, right? And people are like, that didn't happen. I'm like, no, it's literally his private banker from Westbaum Beach.

Like, Marrier. That could be a complete coincidence. I'm just saying, like, if there was a simulation, these are the kind of things that you would definitely throw at us. Guys, I actually want to talk to you a lot about a lot of things. Can't read anything you're saying. So I have to end the stream. But I will tell you this. Today on The Daily Wolf, there's not much news, which seems to be a Friday.

thing. So we're, we're, we're, we're, we're, we're, I'm going to do a deep dive into the genesis of Bitcoin's Toshinacomoto, why it matters, why it's so important. I think it's going to be really good, honestly. I think it's going to be great. Um, not to shoot my own horn. But I'm pretty good at this. All right, guys, that's all I got for you today. I will see you on Monday. It's been amazing. Macro Monday will be back this Monday. I know you were dying without it this week. See you guys later.