Raging Moderates with Scott Galloway and Jessica Tarlov - Trump Cashes in on Thousands of Stock Trades While Americans Get Crushed

Episode Date: May 18, 2026

Scott Galloway and Jessica Tarlov break down explosive new ethics filings showing that President Trump made thousands of stock trades during the first quarter of 2026, with transactions totaling hundreds of millions of dollars. While the White House insists the trades were handled through trusts and third parties, the revelations arrive alongside reports that Trump has secured a massive $1.8B fund from his own DOJ to be distributed to allies or supporters who were investigated during the Biden years. Scott and Jess also unpack growing speculation that the administration could be laying the groundwork for a future military operation in Cuba, following new sanctions and eyebrow-raising intelligence claims involving military drones. Plus: Senator Bill Cassidy became the first Republican senator in nearly a decade to lose a bid for renomination, after voting to convict Trump in his second impeachment trial. They discuss how this outcome reinforces the Trump-centrism of the Republican party, and the political risks of dissent in today’s GOP.  They also dive into the increasingly bizarre Los Angeles mayoral race, where reality TV personality Spencer Pratt is gaining traction. What does his rise reveal about voter frustration, celebrity politics, and governance in the state of California? And finally: Gen Z graduates are openly booing tech executives promoting artificial intelligence in their commencement speeches. Does it mean that Gen Z is fed up with AI? Or are the boos a reaction to the generational anxiety about automation, income inequality, and the future of work? For ad-free episodes, exclusive livestreams, and to connect with Scott, Jessica, and the Raging Moderates community, join us at ProfG+ on Substack: https://ragingmoderates.profgmedia.com/ Get The Monday Rage newsletter: https://profgmedia.com/s/monday-rage/ Follow Raging Moderates on IG, Tiktok, and Facebook: https://www.instagram.com/ragingmoderatespod/ https://www.tiktok.com/@ragingmoderates https://www.facebook.com/people/Raging-Moderates/61586910127414/ Follow Jessica Tarlov on Instagram, Substack, and Bluesky: https://instagram.com/jessicatarlov https://substack.com/@jessietarlov https://bsky.app/profile/jessicatarlov.bsky.social Follow Scott on Instagram, Substack, and Bluesky: https://instagram.com/profgalloway https://substack.com/@profgalloway https://bsky.app/profile/profgalloway.com Subscribe to our YouTube Channel: https://www.youtube.com/@RagingModerates Learn more about your ad choices. Visit podcastchoices.com/adchoices

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So why not you? Try Odu for free at Odu.com. That's ODOO.O.com. Welcome to Raging Moderates. I'm Scott Galloway. And I'm Jessica Darlov. Some quick housekeeping before today's show. We're now ad-free on substack. Join Prop G-plus for exclusive live streams, ticket, pre-sales, community access, and our weekly newsletter, the Monday Rage at Raging Moderates.com. Again, that's ragingmoderates.proptuMedia.com. And if you're watching on YouTube, do us a favor and clip the subscribe button on our YouTube page. It's free and helps us stay relevant in the algorithm. Okay, let's get into it.

A newly released ethics filing shows that President Trump made over 3,600 stock trades during the first quarter of 2026, with a total value somewhere between 220 million and 750 million. The White House says there are no conflicts because the trades are managed by trusts in third parties. At the same time, the administration is considering a $1.7 billion taxpayer fund and compensation fund for Trump's allies. investigated during the Biden years, while Trump himself continues seeking restitution tied to past probes. Jess, this comes as Americans are getting crushed by inflation, rising gas prices, and mounting debt, yet the White House increasingly looks like it's up for sale. What's your take? I have been raging, hot and bothered, upset all the feelings about this for the last few days

since this report came out. We talked about it on the five. I do try to not raise my voice when I'm having a lively conversation with my colleagues. It was so loud in the studio. I could not believe the defense of these behaviors. And this idea that it's managed by a trust and he doesn't have access to it, the guy went up 118 spots on the Forbes list last year alone, made $3 billion while he's in the White House. And his defenders say, well, he doesn't take a salary. Yeah, I wouldn't take a $400,000 salary if I could have $3 billion. instead. And part of their argument is also that, well, he was a businessman before. So what do you expect him to do? I expect him to take a break. That doesn't mean that there aren't going to be people who

want to do business with you afterwards, right? Or that there aren't some, you know, back channel ways to be making a bit of money on the side while you turn yourself over to public service. We're talking about billions of dollars. And these stock trades as everyone is focused on what happens in Congress, right, that I have to hear every day about Nancy Pelosi's Talente gelato tray. And you're going to be out there. And she isn't even in the top 10, by the way, I should note. But that's the one that everyone always goes to. And then Donald Trump is trading the stocks that he's overseeing mergers that relate to them. Warner Brothers, Paramount, Netflix, Palantier, were in a war, right? Palantir is doing pretty well. He bought a one to five million dollars worth of Dell

stock and then nine days later gives an economic speech in Georgia where he says, go out and buy a Dell computer. Phenomenal products. No, I'm not sure if he's actually connecting point A to point B on that. And if he thinks like, oh, I just went and bought these stocks or my manager, you know, Eric Trump, Don Jr., or whoever does it. But it feels like insider trading to me. And I want to talk about all the polymarket stuff as it relates to the war. But how can this go on? Yeah, so there's two things here, just in terms of norms. Every president since LBJ has used a qualified blind trust. Jimmy Carter liquidated his peanut farm.

Obama just had index funds and treasury notes. And so it all sort of adds up. When you look at the fact that he's making 40 trades per day, and he typically throughout his life has made less than that per year, it feels as if all of a sudden he's either got just this incredible love for Robin Hood and trading stocks, or he believes there's a way to make money here because he has access to information that other people don't, and you can trade on that information, which is the definition of insider trading. And I think that just some of the timing here in fact pattern is really damning.

You referenced the Dell trade. I think it was before he carved up TikTok and gave it to a small number of his buddies, including Michael Dell, the Nvidia trade. There's just certain things here that those look nakedly like upon further scrutiny would qualify as insider trading. 3,600 trades in a single quarter. I mean, what he's effectively decided is, and I believe this is a function of the following, you know, Rudy Giuliani said, had this thing where if you let one window go broken and you don't prosecuted or follow up on it, every window gets broken. And I do believe that. I do believe that. that there's been corruption on both sides of the aisle in terms of allowing our elected representatives

who sit in in confidential security briefings where there's huge allocation of capital and health briefings and health and human services. People from both sides of the aisle have been making hundreds of thousands of dollars, sometimes millions. You know, the Pelosi portfolio is up 600%, Berkshire Hathaway, 300%, the S&P up 200%. And he said, you're all smallball, you're all chumps. I'm going to make billions, whether it's a crypto coin or potentially trading on decisions. More than anything, I think what we're going to find is that he has purposely created volatility such that he could trade off of it. So he has thrusts the world into chaos for profit is, I think, the thesis that should scare the shit around everyone. The specific trade that is the tell is the Oracle purchase. He bought millions in Oracle stock

in early 2026 around the same time his administration was helping Oracle secure the TikTok operating deal. So this all, I don't even think of this as a conflict. I think of this as a business model that the president has decided he can get away with. And the reason why we have these laws, well, one, the president, we have these norms or the president's not supposed to be monetizing the full faith and credit and influence of the United States. And two, the reason we have these laws more generally is that if you buy a stock and you don't have insider information, there's now a decent chance that the person you're buying or selling from does have insider information, and you're going to get fogged.

It's like that old saying, if you don't know the dumbest person in the room, that means you're that person. So people are going to stop investing in these markets when they figure out that a lot of these trades are from the wealthiest man in the world who said, I've got funding secure at X price, and they buy on that information, only finding out it's a law, and then there's no punishment. and that if they buy or sell Oracle or Disney stock, they're not one of the people on the inside knowing what the FCC is or isn't going to do, or if they're selling or buying options on West intermediate crude,

does someone on the other side know what the president is about to announce in the next 24 hours? So this reduces faith in fair play around the markets, which is central to attracting capital from all over the world. And again, I just don't think this guy gives us shit. I think he feels immune. He can inspire an insurrection. He can create a crypto coin.

he can be found guilty of civil sexual abuse, and it doesn't matter. And so I think he's just decided I'm immune, and his number one incentive is to go from whatever it is, a hundredth on the Forbes list to one. I think that's his goal. Well, he feels immune because Supreme Court has made him immune, and our laws have made him immune, and the fact that we, the people who we elect to represent us have no backbone. And so they have also made him immune. I mean, that all of this is going on.

I mean, like, think about the field of what's going on with Donald Trump. So he has a record on popularity, right, 32% approval rating, the Bush line, as Sarah Longwell likes to call it. Democrats in the New York Times-Siena poll are up 11 on the generic ballot right now. There are still problems with the Democratic brand. We will get to it. You know, we love to focus on what our side is doing wrong as well. should have a pretty good midterm, certainly if anything close to an 11-point advantage comes to fruition. 70% of Americans say that they're angry with Trump's approach to the economy around the

same amount thinks that he doesn't care about cost of living. There's only Pete Hegseth approves with the war in Iran, basically. It's like one dude that's really into this point. And, you know, Trump every other day thinks that it's a lot of fun when he wants to call up Axios and feed them some more about it. So you've got that going on in the background. Trump comes out and says, I don't care about your financial situation. Affordability is a hoax. Also, I'm going to go over here. I'm going to make all of these trades. I'm going to make all of these real estate deals. Jared Kushner, all of them. I mean, the kids getting the no-bid contracts for their drone companies, the robotics companies. I mean, they actually make Christy Noem look like a totally reasonable above-bored human being with the level of depravity that we're seeing. And then he's going to drop his $10 billion lawsuit against the IRS for leaking his tax. returns in exchange for a $1.7 billion slush fund, which is for allies who have been targeted by the Biden administration, whatever the fuck that means. Right. So that's basically just like anybody. We're going to end up what, giving money to Roger Stone or Paul Manafort or this

crazy cast of characters who have, you know, gripes with the quote unquote deep state and, you know, want to put Jim Comey in jail for some seashells. Like, if you're watching this from outside, I mean, you're watching it from inside and you want to kill yourself. But if you're watching it from outside, even if you're in a banana republic country, you're thinking like our guys aren't even this messed up, right? It's like, it's blowing my mind. And then 60 minutes last night, which was incredible looking at all of the potential insider trades. Like, I didn't know that if you have a 52% success rate, that that's what indicates some degree of systemic insider trading. these accounts have 98% hit rate.

Infallible. Like, as absolutely astounding. You got $800 million that's been one off of oil prices dropping. And then the millions on the military operations. And there's this data analytics firm bubble maps. That's who they were talking to about this. And they were discussing how polymarket, which lets you bet on these military operations,

is really vulnerable to corruption because so many people have insider information. for that, right? Like, I know these briefings, we're supposed to think that it's only like four people who know about it, but that's not true. And then they call somebody or they go out into the hallway and they talk to their favorite, you know, rep member of Congress who gets on TV and then says, I was in a classified briefing and this is what I can tell you. And that's sometimes even good enough for someone to be able to go and make a smart bet about it, let alone if it's Pete Hegseth or Donald Trump or someone who really, really knows, that's feeding it directly to these accounts, which apparently the Polymark at ones that they're linked to one another. Sorry, that was a lot, but I told you I'm bothered. Sure. Well, I think you're bothered, justified. The notion that the president, unlike every other previous president, did not release

his tax returns and then they were leaked. So he's suing his own government agency that he oversees. And then he gets to decide how much the fine is that's going to be paid to him. It's just, I mean, I think Putin is just sitting. there in an admiration, like, wow, that is really good. I even I couldn't come up with that one. I do think the speculation markets or the prediction markets, I think the insider trading there will mostly be not starched out, but diminished, because I think the markets where there's a potential for tons of insider information will have trouble attracting capital, because I think

people are going to start to figure out, if I don't know what's going to happen here, I shouldn't bet on this. And even with a stock, with stocks, it's a little bit different. If it's binary, will Venezuela have, will the U.S. take military action against Venezuela in the next 72 hours? That's a binary outcome. I have had, I met on a bunch of boards of companies that had just a shit ton of information, or I've been pregnant with insider information. And what I have found is that unless it's really obvious, unless your company is being acquired for 18 bucks a share in the stocks trading at 11 and you're announcing it Monday morning at 9 a.m. I would have lost money if I'd bet on what I thought was insider information. In other words, stocks move in such incredible

weird ways, unless it's very direct information. Like, you have an earnings beat, but the analysts were expecting a bigger earnings beat. My point is, insider information in the stock market, unless it's really binary, it oftentimes doesn't pay off to the same extent. Whereas the speculation markets have binary outcomes. But I do think the existential risk in our financial markets is people start thinking the game is even more rigged. And the game is rigged now towards people who have the money to invest in stocks because they're the owners, and this is more about tax policy, but the owners get to see their wealth compound tax deferred versus the earners who have to, you know, get clipped 10 to 53% every year. Ninety-eight percent of the noise around this is, well,

let me say, highlighting it is productive. The noise is indignance. What I want to see is someone running for president, Rahm Emanuel, or Cory Booker, or Gavin Newsom, say, working with the following states Attorney General, I believe that there is so much fraud and so much insider trading here in such a violation of the Malamunds Clause, insurrection, that I'm going to work with different states' attorneys general where I think these crimes took place, and I'm absolutely going to pursue these crimes to the end of the earth, once we have a viable and somewhat credible Department of Justice. And the reason I'm going to work with states, AGs, is that a state prosecution is not subject to or protected by presidential pardons. So I'm sort of done with,

okay, we know he's... It's bad. We know he's willing to engage in this. Fine. What the fuck are you going to do about it. You want to be president, you want to be governor, whatever it is. What's the plan to stop it other than we're better? And by the way, maybe we're not that much. I mean, we are that much better, but let the chips fall where they may. That's my point. And those those prosecutions will also demand the disgorgement of profits by Democrats who have engaged in what is effectively insider trading. Your thoughts? Everybody who's guilty of this, you have no place in public service. That's it. That will be the new threshold. We're always searching for policies. Last week, we had $7,000 for your baby. This week, we have the Insider Trading

Integrity Commission. You will all lose your jobs. You will be prosecuted to the fullest extent of the law. If we need new laws, we're going to get the new laws to make sure that people in public service cannot do things like this. And there's this government agency, the Commodity Futures Trading Commission, which oversees the prediction markets, they better, I mean, apparently the guy who runs it declined to talk to 60 minutes for this piece. I'm not surprised about that. But they better get on it because the prediction markets are moving way too fast for whatever they're doing. They were set up to regulate food prices. This is a very different world here. I do think it is really important. I don't know if Polly Market is considering getting out of the business of, you know,

letting you bet on war. But I don't like that. I think, you know, Kelsey doesn't do it. Polymarket does. I think that should be a line in the sand. You're talking about lives. You're talking about American service members. I know that there are a lot of gross things that go on on prediction markets generally, but war feels like a step too far for our already incredibly gross society, basically.

Okay, let's take a quick break. Stay with us. Support for this show comes from Odu. Running a business is hard enough. So why make it harder with a dozen different apps that don't talk to each other? Introducing Odu. It's the only business software you'll ever need. It's an all-in-one fully integrated platform that makes your work easier,

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So why not you? Try O-D-O-Frey at O-D-O-O-D-com. That's O-D-O-O-O-O-com. Welcome back. So meanwhile, even as the war in Iran is far from reaching a conclusion, the Trump administration could already be angling to shift focus to a new conflict this time in Cuba. Exclusive reporting by Mark Caputo for Axios cited an intelligence source that claims Cuba has more than 300 military drones and is planning to attack U.S. sites. Questions have been raised around whether this is the Trump administration planning ideas to back a future aggressive action toward the island nation.

Jess, the U.S. imposed new sanctions on Cuba earlier this month, but the economic situation there seems pretty dire for them to be plotting a military action against the U.S. What do you make of this? They got to change the narrative, right? I mean, Iran's not going well. The meeting last week with President Xi didn't go well. I mean, we'll see if any of the so-called deals come to fruition and Boeing sells their, you know, their 200 planes, even though I think they wanted like 700 or something like that,

if we get our soybean purchases, et cetera. But they need a narrative. And because Trump was sold on the idea that Iran could be like Venezuela, I'm sure he's thinking, well, maybe Cuba could be like Venezuela. This is also near and dear to Marco Rubio's heart. he is the son of Cuban immigrants. And so this has always been something that has been in his, I was going to say something terrible,

like in his military spank bank, but that's pretty gross. So we'd probably have to cut that out. But you know what I mean? It's like a little pervy also for 11 a.m. on a Monday. But I just don't believe that Cuba is thinking at this moment, we should start drone attacking Guantanamo Bay and Key West while everyone is out there, you know, having their pie and a cocktail.

It seems very silly considering their situation at home. The Cuban embassy posted that, yes, of course, they would have a right to defend themselves, but that's if there's American aggression towards them, not that they would be preemptively doing this. We also have to have a conversation about the leaks from the administration to specific reporters or outlets. I mean, Axios is big on Iran. And now with Cuba, there's a community note on the Axios post. that says, you know, this is based on one official, no verification, which means that somebody wanted to get it out there. I think it's great that there are elected officials like, you know,

Ruben Gallego is out there posting away saying, like, this is a distraction and this is because the administration wants to move in this direction. It's not really based on anything real, you know, scaring us into another useless war. So they got to talk about something new. And you saw that they also, the Justice Department was preparing to seek an indictment against Raul Castro based on a 1996 shootdown of four planes that were operated by the Miami-based exile group, Brothers to the Rescue. He was defense minister at the time. So they're clearly in a Cuban state of mind. And I think looking for a justification and a new narrative. What did you make of it? Yeah. This feels like nothing but a leak to try and justify military action from the U.S.

I just can't imagine in any world where Cuban military officials have said, this is the time to attack. We have absolutely nothing to attack with. It's just, okay, I'm going to take the first swing at the rock for some reason. I'm going to give him a reason to beat the shit out of me. I just don't, you know, 89% of Cuban families live in extreme poverty, 91% negatively view their own government's economic management. Two of the world's largest shipping companies just stopped all Cuba bookings,

potentially 60% of the island's total shipping volume. This is a country that can barely keep its lights on, literally. The electric grid has been destabilizing since January. I don't pretend to be, I know very little about Castro and the Cuban geopolitical situation, but I would argue that the place to start in terms of trying to do a slow democratic, we invaded Eastern Europe in the 80s and 90s with Baywatch and McDonald's, and McDonald's and money in an aspirational life. And that was the best invasion ever,

and that is they decided to tear down the wall and that they wanted their own David Hasselhoff and their own supersized meals. And in my view, the smarter play around Cuba would be to provide economic aid and start investing and trying to figure out a way

to get Chipotle's and Chick-fil-Az in there. But the idea that we're going to go after a nation on its knees militarily, it's for what? to turn them against us. They're already against their own government. It feels to me like this is an opportunity for us to be the good guys,

passing out Hershey bars, if you will. I can't see anything but downside. And the potential refugee crisis that will come from doing this. They hop on the rafts, essentially. And then you think that Florida's going to be happy about what's going to happen as a result of this?

because we have seen that movie before. Yeah, this is a familiar pattern. Administration needs a pretext for military action. It was, oh, no, we're kidding. We didn't take out their nuclear capability in Iran. And now that there's some, quote, unquote, exclusive reporting from a single intelligence source about Cuban drones.

Anyway, let's move on. Senator Bill Cassidy of Louisiana has lost his primary and becoming the first GOP senator to lose renomination in nearly a decade. Think about that. The first GOP senator to lose renomination in nearly a decade. In 2021, Cassidy voted to convict President Donald Trump on impeachment charges following the January 6th Capitol attack.

Trump actively backed his opponents in the primary. Here was Lindsey Graham's blunt warning. Let's watch. Are you glad that Senator Cassidy is no longer going to be your colleague, Senator? No, I like Bill. I thought he's a great senator, but he made a political decision. Bill Cassidy's lost because he tried to do. destroy Trump, Massey's going to lose because he's trying to destroy the agenda. You can disagree

with President Trump, but if you try to destroy him, you're going to lose because this is the party of Donald Trump. He didn't just like decide to destroy Donald Trump. He voted to say it's a sunny day outside and the sky is blue and Donald Trump fomented an insurrection and he should not be able to serve in office again, which is what the conviction meant. Like he'd already been impeached by the House. I really think the lesson for Bill Cassidy, I want to talk a little bit about his comments and his concession speech is you can't go halfway with being principled. If you're going to do the conviction, then you also don't vote for RFK Jr. It's a great way to put it. Right? Like those I want to have it both ways. Yeah. Yeah. And say, oh, I'm a great ally of President Trump. I worked

with him. I think he had four issue areas or four bills that he worked with the president on. Like, are you a two-year-old and you can't remember what you did yesterday? or what you know about this man, this man holds grudges from when he was in kindergarten, right? And you think he's going to forget that you were one of six that actually had the guts to vote to convict him?

And in his race, Trump embraced both of his opponents. So now they're headed to a runoff. The two of them, and Cassidy says, let me just set the record straight. Our country is not about one individual. Lies, your party is just about one individual. Lindsay Graham is right.

It's about the welfare of all Americans. Well, why did you put RFK Jr. in charge of our health care? And it's about our Constitution. Dude, total betrayal of all of that on every, all of these levels. And, you know, Trump gleefully posting on truth social Saturday night, his disloyalty to the man who got him elected is now part of legend. And it's nice to see that his political career is over in all capitals. This man is so crass and nasty. And he shows you who you, who he is every day. Why do people think it's going to end differently for them? Yeah. The Republican Party is no longer a political party. It's a protection racket with a primary calendar. And

unfortunately, it's very effective. And Cassidy wanted to have it both ways. I'm a doctor. I took a Hippocratic oath, so I'm worried about vaccines, but I'm going to vote for the spread of measles by confirming RFK Jr. because I don't. I'm scared. He's survived the impeachment vote, he could come for me. And I'm sympathetic to the notion that, okay, you got to get reelected to do good. And if you don't get reelect, there's certain political realities. But for a doctor who, he directly violated his Hippocratic oath. He knew that RFK Jr. was a menace to public health. And he voted for him anyways. He could have very usually stood on that ground. The, you know, the problem is, be careful what you wish for. The guy

that's going to replace them is probably going to be even worse. And so it's fun for Democrats to say, you know, Dr. Cassidy, you should be, you should have your license revoked. This is how weak sauce burns you or scalds you. But, okay, now the next guy's going to be going to be worse. The only silver lining here is I can't wait to see the new testicles they're going to emerge from Senator Cassidy over the next six months. All of a sudden, like all of these Republicans who realize their political future is over. He'll find the tomtellis sauce. All of a sudden they'll be like, a truth teller, a real leader, calling it how, calling it as he sees it, standing up to the president. Well, good for you. I can't wait for his first appearance on, on Bill Maher,

about how he's going to be a truth teller once his political fortunes are no longer subject to dear leader. Or his first appearance on raging moderates. Oh, let's bring him on. The, Julia Letlow, and she's a congresswoman who is advancing to the runoff and state treasurer John Fleming, are the folks who, you know, could get his seat. Very, very, very, very Trumpy. You're, you're right. I think, you know, would you rather that it was Bill Cassidy versus somebody who never has any moments of seemingly being grounded in reality vis-a-vis Trump or just, you know, would you rather? you know, the Constitution or even healthcare. Because Bill Cassidy has had moments in hearings, right, where he has pushed back and said...

It's good to have a doctor. It's good to have a doctor. Yeah. But, you know, they are just ruthless about this. And so I don't want to sit around, I guess, crying for what could have been if Bill Cassidy had, you know, not voted for RFK Jr. or whatever. They all reveal themselves to be fundamentally just concerned with what Donald Trump says and what he's doing and what he's going to do to them. And so maybe it will just be

easier if it can be a hundred percent enemy of the state, right, if they're just full Trumpy. And then maybe that shifts more elections towards people who can be more reasonable. I don't even say just Democrats. They're a really interesting independent candidates like Dan Osborne in Nebraska, who actually in a poll was up four on Pete Ricketts, which would be a modern day miracle. Also on a branding front, I'm going to send this to you. You'd really like it. Dan Osborne always puts the color on his ads. He's in a red box and he puts Pete Ricketts in a blue box. So he's the one who looks like the conservative, even though he is left leaning. The Thomas Massey question, though, is the next most interesting piece of this. So his primary,

Trump is going after him. It costs $35 million already. And I looked it up. The average primary costs $100,000 to $500,000. So that's how much they're spending. APAC is spending millions against Massey. Donald Trump has made it his business. If you're one of the four Republicans who signed the discharge petition for the Epstein files, he's coming for you. Marjorie Taylor Green, Lauren Bobert, Nancy Mace, and Massey. We talked to Rand Paul when he was on about this. Paul is putting a lot of capital behind defending Massey. But, you know, big guns are coming in. Pete Huggseth is going to campaign there, Speaker Johnson. What do you think happens to him in his primary? You know, the honest answer is I don't know. I haven't been following the race. I got to be honest, I just love the fact that Representative Bobert, I would affectionately call a village idiot, is Trump's coming from. I mean, I love it when the enemies turn on each other. So, look, you know this better than I do. How does the race and Massey see what? I'm knocking on wood. I think he survives the primary because I think that where Massey is different from like a Bill Cassidy is that he's consistent, right? There's been no comprehensive.

of anything. And like, I'm always astounded, you know, I guess it's the way my algorithm works that I get, you know, all excited about this Republican that's pushing back against Trump. And then like with Rand Paul, we have him on. And he's like, I vote with the president 95% of the time or whatever it is. It's just like the one time that, you know, they step out, right? Then it floods our social media. And we think that there's, you know, some sort of breaking. But Thomas Massey has been consistently in Thomas Massey. and has been talking about this issue and the work that he and Rokana are doing together is really important not only for the survivors of the Epstein cabal, I don't even know what you would call it,

but just, you know, to know that there are some principled conservatives left hanging around. You know, he does a lot of media. He very openly, you know, talks about the lengths at which they're coming after him,

the personal attacks, the threats to his life, His wife passed away. He remarried. Trump's even gone after him about that. I mean, Trump, like a guy who's cheated on every wife that he's ever had. And, you know, he's going after Thomas Massey for taking care of his wife of decades and then finding love with someone else. And a very good glow up, I would say. He's been. That's not nice to say. You don't care about the glow up. But Thomas Massey had a glow up. And it's very good. driven. I like to I like to, I find, I love to objectify people, so I have more fun objectifying men because I find I don't get into trouble for that. He's not like Gavin Newsome yet, but it's

looking better. Yeah. Let's take one last quick break. AI is moving fast across the enterprise. But without visibility, it's just chaos. Different tools, different models, different teams using AI in completely different ways.

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The future of law is agentic, not just 20%. tools that assist, but AI agents that navigate complex matters. That's why Harvey created agents that can do the work from end to end. They build a plan, pull from secure data sources, run subagents in parallel, and draft the work product ready for your review. So you delegate the work and on the judgment. Trusted by more than 60% of the AMLA 100 and leading Fortune 500 legal teams, Harvey is the AI operating system designed specifically for legal work. Harvey, AI, tailored for Law. Learn more at harvey.a.ai. Welcome back. Let's move on to something from my hometown, Los Angeles, the mayoral race there. Spencer Pratt specifically is getting a lot of national attention.

A friend of mine that I've known since the fraternity called me and asked me to have them on the pod here, and I said, we're not really interested in mayoral races, but if it gets weird enough, maybe we'll have them on. Maybe we'll have to have both. That's how it works. That's how you're responsible. That's what I hear. That's how you do this in media. Yeah. So Los Angeles has spent more than a billion dollars annually on homelessness every year for years and still has 43,000 people living on the streets. The Palisades' fire recovery is widely seen as botched.

Residence satisfaction is at historic lows. Cali currently has Pratt at a 28% chance of winning the race, and the primary is just two weeks away on June 2nd. I have been shocked. I haven't lived in Los Angeles since I live shortly after. I'm a graduate of UCLA, but I go back a lot. And I find it's turned into a series of like, almost, I would describe it almost a little bit like Johannesburg or Cape Town, and that there's some areas where the rich people live that are like Elysium. And then if you venture out of those areas, it gets just so ugly, so fast. And it feels like what people describe California now

is ungovernable because of insurance special interest groups that took up so much money. you know, the product is expensive but bad in the sense that in terms of government services, right? And Pratt's own home burned during the fire. And he's got, he does have, whatever you think about him, he's got an authentic origin story in the race. Grievance plus relatability plus name recognition, you know, spells politics. And L.A. created this, a decade of institutional failure handed a reality TV villain, a visible candidacy. If nobody clears 50% on June 2nd. It goes to November runoff. Spencer Pratt and a November runoff for Mayor of Los Angeles. This is wild. Any thoughts on Spencer Pratt and Mayor Bass? Well, we've been talking about it a lot on

the five. And that hasn't gotten as loud as it's okay for Donald Trump to be trading stocks and making billions of dollars. But it's gotten a little frisky for sure. I think that Mayor Bass is missing an opportunity to essentially take Spencer Pratt into her fold and co-op some of the things that he's talking about and then neutralize him at least a little bit. The guy is still a registered Republican. He's running an independent campaign, but he's a Republican. And partisanship goes a long way, especially in a town like Los Angeles. That is not being amplified that much. There are also rumors that there's a production company that's going to be filming all of this. You know, once a reality TV star, always a reality TV star.

You know, I think TMZ is on it now and found that in the ad that he filmed in front of the Gulfstream that he was living in. He's actually been living at the Bel Air Hotel. Like, I get it. It's fine. He has a lot of money. There is opportunity to do that. His house did still burn down.

But there are aspects of Prattom that I think. think are a little bit unsavory for folks when they look beneath the hood, some more than that. And I think that Bass needs to really up her game if she wants to win this. She needs to also convince the councilwoman who's running as well to drop out so that it is a two-man or one-woman and one-man race because of the way the jungle primary system works. But it is a test of social media virality. I mean, a lot of this is our impression of what's going on from our algorithms, right? Like, I saw that ad that he did the AI ad where Mayor Bass is the Joker, right? Like, that was everything that I was seeing and all of this hugely positive reaction.

And there are some celebrities and powerful people in Los Angeles. I imagine, like, whoever you're friends with that reached out to you about having Spencer Pratt on as well. But, you know, there are models now for Democratic governance in blue cities that everyone should be looking to. Like Dan Lurie in San Francisco, he's now the most popular mayor in the country, 74%. I was in San Francisco just a couple months ago. I'm not saying it's perfect. I still saw some people doing drugs in the mission. But I was staying on Market Street, I wasn't scared.

I wasn't stepping over anyone. Businesses are starting to come back. Obviously, the Super Bowl was a huge boon for them. San Francisco is gorgeous. And restoring it to that is deeply important, not only to California, but I think for the country. And I think that, you know, if Bass was like, I'm going to do a Dan Lurie here, right, I'm going to force people off the street who shouldn't be here, right? You get you into treatment wherever you need to go. We should never have a situation where there are prostitution rings near a preschool. We shouldn't have to have websites for

tracking where there's poop on the street, right? Like all of those things would, do her a lot of good and keep him at 27 percent or even decrease that. She's, you know, looking to win re-election. A lot of people say L.A. is ungovernable. I mean, one of the things, one of the lessons I think mayors should take. And like, if Democrats don't figure out a way to actually so they can operate a city, it's going to haunt us in national elections. And one lesson I would take from Mayor Lurie or I think other Democrats should take is

no one gives the fuck what you think about Israel or Ukraine or even national politics. just make sure Bart runs on time and that if you're paying a ton of taxes, your kids don't have to see a homeless person masturbating on the corner. It's like, okay, everybody pretends they're starting that when they're elected mayor, it's their kickoff campaign for president.

No, you're there, you're an operational executive. Just focus on the boring shit, and that's what Mayor Lurie is doing. I even, we interviewed him on our Pivot Live tour. Oh, yeah, I was so jealous of that. He refused to talk about national politics. It's just like, that's not why I'm here. I'm not, you know, I'm totally focused on the P's and the Q's of the city.

And that is exactly the right conversation. Los Angeles, it's so poorly governed. I imagine there's enormous entrenched special interest groups that make it very difficult to get anything done, very expensive to get anything done. I was trying to convince my friend Jamie Patrickoff to run. He's thoughtful, he's smart, he's nice, he's a business person. He has the money, and I think that's important. And he loves that city. He's betrayed us, New Yorkers.

He grew up here, too. He's Mr. L.A. So, you know, but like, let's keep in mind, Spencer Pratt for all his likability and camera-ready social media. He embraced Alex Jones. He said the 9-11 was an- Yeah. We play that clip because it is bad. Yeah, we should play that clip.

Let's play that clip. Like, I know from watching you for years that you're not like, I know people are going to eat me alive for this, but a bad guy. But then people see this whole Sandy Hooks. in that they have and they're like, he doesn't believe parents in the baby, you know, the negativity in my app mentions and everything is when I said we're going on. People are like, he does, there's a baby, this. I'm like, he's not like that. No, he's like that. So let me just back up. Spencer Pratt, we were thinking about having him on. Mr. Pratt, go fuck yourself. We are absolutely not going to platform your bullshit conspiracy theory. And yeah, L.A. needs help. It does not need you.

Anyways. I like that response better. Too much, Jess. Too much? I mean, I was trying to be all, like, policy-oriented, but I'm cool with, like, F you if you think Alex Jones is an okay guy. Yeah, and, you know, hold the doubt around Sandy Hook. Yeah. Yeah, brother, do your kids go to school? Anyways, let's move on to something lighter. So I don't know if you saw this, but basically, with commencement season when graduates celebrate their achievements and show their disdain for peddling the future of AI, this year's graduates, many of whom relied on AI tools throughout college, not only enter one of the toughest job markets in years, they've loudly booed commencement speakers praising AI, including Gloria Cofield at the University of Central Florida and former Google CEO Eric Schmidt at the University of Arizona. Let's play a clip. The question is not whether AI will shape the world, it will. The question is whether you will help shape artificial intelligence. We do not know the precise contours of what this transformation will look like.

If you don't care about science, that's okay, because AI is going to touch everything else as well. Whatever path you choose, AI will become hard of how work is done. You can now assemble a team of AI agents to help you with the parts that you could never accomplish on your own. When someone offers you a seat on the rocket ship, you do not ask which seat. You just get on. No, they don't. So I want to talk about this for a second. Then I'm going to do what I always do and bring it back to May.

I think this is a, I don't think this is a statement on AI. I think it's a statement on income inequality. And that is we continue to transfer so much money from younger people to older people. We have raised the cost of education. We've monetized education. We've monetized housing by sequestering housing permits. We tax the shit out of earners, which most of these kids are about to become, such that older people, i.e., owners, can see their wealth compound. And we tax them such that we can make the wealthiest generation in the history of the planet, seniors, more wealthy with Social Security, a third of whom do not.

need it. And these guys, they've had it. And not like that, their use of AI, and let's be honest, they're all using probably AI more than most of the people they're booing. Their lives are being monetized. Their attention is being monetized. Their propensity to addiction and need for affirmation is they go through puberty in high school and college is being monetized, such that my generation can get ridiculously fucking wealthy. And they're angry. So the AI was just a red herring or a straw man or whatever it is, an excuse to sort of exhibit the rage. And my, I even saw it my buddy, Jonathan Haidt, was controversial as a speaker at NYU. There's few people that have tried, not only tried, but been more effective at trying to help young people than Jonathan Haid. Young people

are so frustrated that anyone who gets on the stage that they did not pick who's over the age of 40, specifically if you're some white person, they're just going to boo you because they're just, just fucking fed up, and I understand why. And the solution to all of this, in my view, is for the student, it's their graduation, they should select the speaker. Not some committee, and this is, and I'll bring this back to me because I never missed an opportunity to glaze myself. I was selected as a student commencement speaker at Berkeley. Cool. Yeah, me and Secretary Clinton, our careers took divergent pass. But I knew nobody was. But I knew nobody was. was going to boo me, or I wasn't going to be humiliated because I was standing in front of people

who were happy for me because they had selected me. And also this year I was asked to speak at commencement at a school at UCLA. And that was the easiest and quickest know I have ever given. Because the people asking me to do it with the administrators. And I don't want to stand up in front of a bunch of young people and lecture to them, as I sit here, having benefited from so much that they don't have access to right now. And despite what I think is a lot of these speakers probably are well-intentioned, these kids are fucking enraged. So give them an excuse to boo you, and they're going to do that, because you're standing up in front. Eric Schmidt, who is a thoughtful guy, a smart guy, I think a good person, who's worth $40 or $60 billion. Okay, AI, whatever,

it is, boss, you've decided to monetize my addiction, monetize my education, monetize my health care, and you're going to give me advice? Fuck you. So I get their rage. This isn't about AI. This is about young people saying to an older generation, stop using my credit card so you can upgrade from Carnival Cruises to Crystal Cruises and then show up and lecture me. Your thoughts? Well, it's really cool you got asked. I agree with all of it. I feel like, I don't know. I mean, maybe you get lucky.

And Roger Federer is your commencement speaker. His Dartmouth speech was incredible. Hans Solo. Harrison Ford was well received. Yes. But Eric Church, the country singer, it seems like, was the number one of this season. Besides Andy Cohen, he did Washu, which I loved. But Eric Church, really, really powerful stuff.

It was a, he went to UNC talking about the six strings. Anyway, I would recommend it's all over social media. That's great to watch it. You know, it's a, it's a performance and a speech. Very inspirational also about how unique and important each of us are. And in the time of AI, a la, all of the booing, for kids to be told that they are unique and important, I thought was incredibly powerful. So that's my Eric Church plug. Nice.

Okay. All right. Should we leave it there, Jess? Well, what, I mean, I could hang. Let's leave it there. Go watch Eric Church's commencement speech. Jess, I'll see you. What? I'll see you tomorrow. Tomorrow. Is that right? Don't worry. All the days are mixing together. I'll see you tomorrow. I don't even buy green bananas anymore. I'll see you tomorrow.

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