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Scott Galloway
Welcome to the week from Prof. G Media, where we break down what mattered and what it all means. George I'm George Hahn, and it's Friday, May 22nd. This week we talked a lot about rules. Rules around war, rules around markets, rules around political power and what happens when people making decisions stop following them. Let's get into it. On Wednesday's Prof. G Markets episode, Ed sat down with Anthony Scaramucci, former White House communications director and founder of Skybridge Capital, to go through the 3,700 plus stock trades the President made in the first quarter of 2026. That's more than 40 trades a day altogether, valued somewhere between 220 million and 750 million dollars. And as Ed laid it out, a lot of those trades weren't random.
Ed (Guest or Co-host)
January 6th, he buys up to up to a million dollars worth of Nvidia stock. And then January 14th, just a few days later, he approves Nvidia to start selling chips to China. That to me is like, okay, that's a very big deal. Similar thing happens January 12, he buys a bunch of Oracle stock. A week later, the deal for Oracle to buy a stake in TikTok is finalized. And of course, the only reason it's finalized is because he approves it. His administration approves it. Similar thing with Boeing. He buys Boeing stock and then he says that China is going to purchase all these Boeing jets Like there are several examples here where it seems very, very plainly ob that he had very important material, non public information. And this is just the way that the law talks about it. And then before that happens, he goes in and he buys the stock. And so in those cases, to me, I'm thinking that's just illegal.
Jess (Co-host or Guest)
You know, I guess there's three things I wanna say. Number one, it's disgusting. It's probably legal, Ed. That's the irony of the whole thing. They've created these loopholes for themselves, but it's absolutely disgusting and it makes people feel very cynical and very turned off by politics. Number two, I think this is probably the most important thing about it is he doesn't care. Which means that worse things are on the way. You're gonna see a tsunami of corruptive activity over the next two and a half years and it's gonna be put right in your face. The bottom line is this is going to happen, okay? The bottom line is, for your viewers and listeners, life is unfair. And these guys are sitting there ladling money into their own accounts for their own self interest. And it would be hypocritical of me, Ed, if I just went after the President on this. You have to go after the Democrats that are also doing this. This is a bipartisan thing. Now you can say, and this almost makes me laugh about Trump, and if Galloway was on with us right now, he would laugh at this. Cuz I know the son of a bitch Prof. G would be like, yeah, no, he's right. Trump is doing IT to the 29th power compared to these guys. Okay? So If Pelosi's taken 5 million, Trump's taken 500 million. So all he's done is pumped himself with unethical steroids. He took the unethical steroid needle, he pumped it into his biceps, and he's out there making billions of dollars for himself. But they're all doing it, Ed. Yes, and I think it would be remiss of us to pretend that it's not happening on both sides.
Scott Galloway
And these trades were just one story on raging moderates. Scott and Jess discussed another controversy. The DOJ announced a new $1.8 billion anti weaponization fund created to compensate people who say they were politically targeted by the government. The money comes from a settlement tied to Trump's lawsuit over the 2019 leak of his tax returns. Under the program, a commission appointed by the Attorney General decides who gets paid. Those decisions can't be challenged in court, and the government isn't required to publicly disclose where all of the money goes. Critics argue it rewards loyalty, while supporters argue it corrects abuses. Scott saw something bigger.
Scott (Possibly Scott Galloway or another commentator)
The notion that the President filed a suit against the IRS or someone at. Someone at the IRS for leaking his tax documents. He was the first president to not voluntarily release his documents, his tax filings, and then sue his own administration and then decide to settle the case brought by him. I mean, this is just, it's, it's so circular and weird and it's such blatant corruption that I think Putin is just in total awe and admiration of this guy right now. And the notion that they tried to soft pedal it a bit by saying it's a compensation fund, it's a slush fund for him to do what any good autocrat does, and that is reward his allies and punish his enemies. And this gives him $1.8 billion to go dole out money to people who are willing to commit crimes in support of him. It also creates a real atmosphere of danger around 2026 and 2028, because there's gotta be a general feeling that people think if I show up to a polling booth and start harassing people in Democratically strong strongholds, if I show up to the inauguration and refuse to swear in a Democrat, if a Democrat wins and I commit crimes and I create a series of intimidating actions, criminality, that the President will save me and bail me out because he's now got a $1.8 billion fund to even reward me. I mean, we're not only talking about pardons for these people, we're talking about giving them money.
Scott Galloway
But frustration with the rules extends well beyond Washington. This week, California put on the ballot a one time 5% wealth tax on assets over a billion dollars. The debate on Tuesday's markets episode with Jason Calacanis and Bradley Tusk got to the core of why people are angry and why the proposed fix might not work.
Jason Calacanis or Bradley Tusk
If you are a poor person, right, and you need public housing, you need Medicaid, you need food stamps, you don't care about social justice, you care about the money being there in the budget to provide you with these things. So if California, which I believe it would at the conclusion of, if they do enact this tax, or New York right now has less money to be able to help the poor, then you're not solving for the problem of inequality. You might be solving to make people who are upper middle class and highly progressive feel better emotionally, because they feel like now the people who did better than them are being justly punished. I don't care about their emotional state or needs. I care about helping poor people.
Scott Galloway
And if the conversation this week was partly about institutions weakening at home, China Decode Asked whether America is losing leverage abroad too, James King argued something remarkable happened during the Trump G Summit last week. For perhaps the first time, China looked like it had the upper hand, not because America suddenly got weaker, but because leverage shifted.
James King
The potentially game changing outcome was that the US and China are now trying to work together to put into place what China calls a constructive China US relationship of strategic stability. I know that's a bit of a mouthful, but to me that means they're trying to climb down from a situation in which China and the US are constantly adversarial in their relationship and moving towards a much more stable relationship. And I think one of the pointers towards this is that Trump invited Xi Jinping to visit the US In September this year and Xi Jinping has agreed to go. So there's a measure of continuity there. I think quite a lot of people will be wondering whether or not this really was a historic summit. And in the sense that I reckon China had the upper hand, I think you can see that from the fact that Trump was trying to be as friendly as possible. He said to Xi Jinping, you are a great leader. He said, it's an honor to be with you. It's an honor to be your friend. The relationship between China and the US Is gonna be better than ever before. And I think one piece of essential background has changed a lot in the way these two countries see each other. And that is China's enduring chokehold over rare earth and critical minerals supplies.
Scott Galloway
We'll be right back after the break.
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Support for the show comes from LinkedIn. It's a shame when the best B2B marketing gets wasted on the wrong audience. Like imagine running an ad for cataract surgery on Saturday morning cartoons. Or running a promo for this show on a video about Roblox or something. No offense to our Gen Alpha listener, but that would be a waste of anyone's ad budget. So when you want to reach the right professionals, you can use LinkedIn ads. LinkedIn has grown to a network of over 1 billion professionals and 130 million decision makers according to their data. That's where it stands apart from other ad buys. You can target your buyers by job title, industry, company role, seniority, skills, company revenue, all so you can stop wasting budget on the wrong audience. That's why LinkedIn Ads boasts one of the highest highest B2B return on ad spend of all online ad networks. Seriously. All of them. Spend $250 on your first campaign on LinkedIn ads and get a free $250 credit for the next one. Just go to LinkedIn.com Scott that's LinkedIn.com Scott Terms and conditions apply.
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Scott Galloway
Welcome back. The conversation eventually landed somewhere where rules matter most. War on profgee Conversations Scott sat down with David French, Iraq veteran, constitutional lawyer and columnist at the New York Times. They discussed Iran and one basic who decides when America goes to war? David argues constitutional guardrails aren't technicalities. They exist because democracies work best when institutions hold.
David French
Well.
The Iran war is a really good example of why the law matters so much. So under traditional just war doctrine, you're not supposed to be able to go to war. You should not go to war under the old school just war doctrine unless you're going to war under the command of the lawful sovereign for a just reason and to pursue just ends. Has that happened here in the United States? And the answer is no, because American law requires for the declaration of war that that's a role reserved to Congress. So that doesn't mean that a president can't respond immediately when there is an attack on our forces or there's an emerging urgent immediate situation that requires military force. But even in those circumstances, the president is supposed to go to Congress immediately to get ratification and support of his actions. It is actually very important to the ability of the United States to wage war and to wage war effectively, because if there's one thing that we know from history, it's that democracies that have achieved public support for a war are among the most powerful entities we've seen in the world. So even if you thought it was wise to attack Iran, for example, the fact that we didn't do the constitutional process undermines the entire war.
Scott Galloway
But constitutional process isn't the only thing wars test. They test budgets, institutions, and our ability to honestly account for trade offs. On a recent Prof. G Deep Dive, Scott explored how much war actually costs. Last month, the Pentagon said the war in Iran had cost $25 billion. That number has since been updated to $29 billion. But economists argue that number captures only the narrowest slice of the missiles fired, aircraft deployed, equipment destroyed. The harder costs often come maintaining troops in the region, higher oil prices, inflation, veteran care, and long term economic consequences that outlast headlines and administrations. History suggests governments consistently underestimate those costs. Economist Justin Wolfers discussed that on a Prof. G Deep Dive this week.
Justin Wolfers
Either there is or, damn it, there should be someone inside the White House or inside The treasury saying, Mr. President, bombing Iran upends the global economy, it upends the American economy, and it will affect people's lives in the following Ways, That's a far broader question. Either they're not asking that because this has not been a carefully thought through war, or they know the answer to that and they're keeping it secret. But what I do know is the other group of folks who are trying to price this thing are folks on Wall Street. They're figuring out not the full cost of war, but they're figuring out, what did my new GDP forecast look like, what do my oil price forecasts look like, employment forecasts, and so on. And no matter which way you slice it, Wall street is saying that the true number is at least 10 times larger than the Pentagon saying, but there's an even deeper problem here. Scott, you said, why do we always tend to low ball? And the answer is, that's the nature of war. I might try and fight you. Well, I might meet you in a dark street outside a London pub, and you might say, hey, Justin, do you want to fight? And most days of the week, I'm like, no, Scott's taller than me. I'm not going to. The only times in which I'm going to say, yes, Scott, I am, and then take a swing is when I underestimate the possibility that this is going to be expensive. So it's in the very nature of conflict that I decide to have a swing at you because I think you're not that big of a bloke. And I'm big and tough and strong. And you swing back because you make the exact same mistake. Look, any fight, whether it's a fight with your spouse, a fight down a darkened alley, a war, or your workers striking, you're usually better off not having a fight. You're saying at the end of this fight, something's going to happen. The fight's messy and awful and hurts me, and it hurts you. Let's not have the fight. Let's get to that negotiated outcome. All conflict is waste. And so the only way that conflict ever occurs is we fail to negotiate. Or alternatively, we think we're mistaken by how easy it is to win.
Scott Galloway
By the way, if you want to hear that full conversation with Justin Wolfers, it's available exclusively on Substack. And before we wrap up a quick victory lap, Scott correctly predicted that Elon Musk's lawsuit against Sam Altman and OpenAI was going nowhere. Musk bruised ego, deep pockets, army of lawyers, spent years trying to undo his biggest regret, leaving OpenAI and watching Altman turn it into one of the most valuable companies on earth. He sued for $150 billion. He wanted Altman removed. Here's what Scott said on CNN's Smirkanish
Legal Analyst or Commentator
from a legal standpoint, courts like argument and evidence, not regret and indignance. From a legal standpoint, this is Marvis Frazier versus Mike Tyson. This should be over in 30 seconds of the first round. Musk has no leg to stand on here and now he wants to control the one piece of the Internet on totally baseless legal grounds that he should own it. What could go wrong? This should and will be a knockout in the first round.
Scott Galloway
We'll be back next Friday with a fresh edition of the week from Prof. G Media, breaking down what mattered and what it all means. Until then, we'll see you around the Prof. G Universe.
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Date: May 22, 2026
Host: Scott Galloway
Guests/Co-hosts: Ed, Jess, Jason Calacanis, Bradley Tusk, James King, David French, Justin Wolfers
Podcast Network: Vox Media Podcast Network
This episode of The Prof G Pod examines how the erosion and manipulation of rules—whether in financial markets, politics, tax policy, or war—have transformed the U.S. into a “loophole economy.” Throughout the week, Scott and guests dissect headline-grabbing stories: from presidential stock trading and slush funds in Washington, to wealth tax debates in California, China’s growing leverage, and the true cost—and legality—of war. The episode underscores a pervasive cynicism: as guardrails weaken, power players increasingly rewrite or bypass the rules for personal gain.
[01:17–03:09]
Revelation of Trades:
The President executed over 3,700 stock trades in Q1 2026, totaling between $220M and $750M. Many trades coincided suspiciously with subsequent policy moves.
Legal vs. Ethical:
"It seems very, very plainly obvious that he had very important material, non public information ... that's just illegal." (02:17)
"It's disgusting. It's probably legal, Ed. That's the irony ... they've created these loopholes for themselves, but it's absolutely disgusting and it makes people feel very cynical." (03:09)
[04:53–07:21]
$1.8B Fund:
DOJ announces a new fund for those claiming political targeting—money from a settlement on Trump's leaked tax returns. Decisions by an AG-appointed commission are not challengeable and are not fully transparent.
Scott’s Take:
“It's a slush fund for him to do what any good autocrat does, and that is reward his allies and punish his enemies … this gives him $1.8B to dole out money to people who are willing to commit crimes in support of him.” (05:45)
[07:21–08:25]
“If you are a poor person ... you care about the money being there in the budget to provide you with these things. If California ... has less money to help the poor, then you're not solving for the problem of inequality.” (07:46)
[08:25–10:26]
Trump–Xi Meeting:
For the first time, China appears to have the upper hand, partly due to its dominance in rare earth and critical minerals.
James King:
“Trump invited Xi Jinping ... Xi Jinping has agreed to go … Trump was trying to be as friendly as possible ... [which] is a pointer that leverage may have shifted.” (08:52)
[13:50–18:55]
Legality of War with Iran:
"Under traditional just war doctrine ... you should not go to war unless you’re under command of the lawful sovereign for a just reason ... American law requires for the declaration of war ... a role reserved to Congress." (14:24)
Cost of War:
“Wall street is saying that the true number is at least 10 times larger than the Pentagon [is] saying ... The only way that conflict ever occurs is we fail to negotiate. Or ... we underestimate how easy it is to win.” (16:53)
[18:55–20:13]
“Courts like argument and evidence, not regret and indignance ... This should and will be a knockout in the first round.” (19:39)
“All he's done is pumped himself with unethical steroids. He took the unethical steroid needle, he pumped it into his biceps, and he's out there making billions ... But they're all doing it, Ed.” (03:09)
“Putin is just in total awe and admiration of this guy right now.” (05:45)
“The potentially game changing outcome was that the U.S. and China are now trying to work together ... moving towards a much more stable relationship.” (08:52)
"All conflict is waste ... you're saying at the end of this fight, something's going to happen. The fight's messy and awful ... Let's get to that negotiated outcome." (16:53)
| Segment | Topic | Timestamp | |---|---|---| | 1 | Presidential stock trades & bipartisan loopholes | 01:17–04:53 | | 2 | DOJ anti-weaponization slush fund | 04:53–07:21 | | 3 | California's wealth tax debate | 07:21–08:25 | | 4 | U.S.–China summit, leverage shift | 08:25–10:26 | | 5 | War powers, constitutional process (w/ David French) | 13:50–15:45 | | 6 | Real cost of war (w/ Justin Wolfers) | 15:45–18:55 | | 7 | Scott’s victory lap: Musk v. OpenAI | 18:55–20:13 |
This episode paints a vivid portrait of American institutions under stress. From Capitol Hill to Wall Street, from Sacramento to global summits, the erosion of rules and the rise of structural loopholes have left the public cynical and the elite emboldened. As Scott and his guests emphasize, the real casualty is trust—in markets, democracy, and the social contract itself.