Welcome back to The Best & The Brightest. I’m Abby Livingston, filing from an unseasonably warm Chicago, where I’m in town in part to take in the Midwestern election vibes.

In tonight’s edition, we’ve got John Heilemann’s very impolitic conversation with Mark Cuban, the dotcom billionaire turned TV personality and former Mavs owner who’s emerged as a sort of liberal antidote to Elon Musk—and, more recently, an unofficial surrogate for Kamala Harris. (All he wants in return is for her to dump Lina Khan as chair of the F.T.C.…)

Mark and John get into Musk’s strange-if-predictable peregrination into Trumpworld, why he likens Harris to a startup C.E.O., how her policy proposals might benefit entrepreneurs, Trump’s remarkable economic illiteracy, and much more.

But first… I’m counting down the days until campaigns file their campaign finance reports ahead of the October 15 deadline. Here are the ones I’m reading…

• Virginia’s 5th: In many ways, the district hasn’t recovered from the emotional scars of its brutal Republican primary, in which the Kevin McCarthy-backed John McGuire ousted Rep. Bob Good as payback for his vote to boot McCarthy from the speakership. (Good also got a push out the door from Trump, as payback for supporting Ron DeSantis.) Now, some Virginia Democrats have started to smell an opportunity. As of his last report, McGuire was all but tapped out financially, filing $116,000 in cash-on-hand in mid-July. (Although he might post a strong third quarter, thanks to contributions from those looking to cozy up to the prospective congressman.)

  Meanwhile, McGuire’s Democratic opponent, Gloria Tinsley Witt, has already filed her October report. The total raised is meager—just $277,000 at the end of the quarter, with $91,000 in cash-on-hand—but Witt is running a surprisingly sophisticated federal campaign leveraging digital ads, operational support from the Virginia Democratic Party, and a small radio ad buy. In other words, this race feels weird, and a McGuire victory is not a foregone conclusion—despite its Republican bent.

• Texas’s 28th: The prevailing assumption is that beleaguered Democratic Rep. Henry Cuellar will survive, but Republicans are eager to mount a massive offensive for this South Texas seat next term. Cuellar’s first report, after his May indictment for bribery and money laundering, was his weakest of the cycle, reporting only $215,000—but was far from the fundraising collapse that other members have faced under these circumstances. However, the report revealed that some prominent Texas Democratic insiders, notably former Rep. Chet Edwards, are still donating to his campaign. Cuellar has $351,000 in cash-on-hand, which will go far in South Texas, a relatively inexpensive place to run a campaign, and he’s a known workhorse. Meanwhile, my understanding is that while Republican nominee Jay Furman has not earned the N.R.C.C.’s blessing, he has hired some serious Texas Republican talent to juice his campaign.
• Florida’s 13th: Republican Rep. Anna Paulina Luna is a fundraising juggernaut. She raised $2.3 million as a freshman, and reported $917,000 in cash-on-hand in July. Many of the donations from her summer report were recurring small-dollar donations from retirees, meaning she can go back to that well again and again. That said, her Democratic opponent, Whitney Fox, has made numerous national media appearances over the past few months, and she has other Florida Democrats behind her. Fundraising in a perceived safe Republican seat is always difficult—Fox has raised just under $850,000 total and posted $119,000 cash-on-hand in her last report—but a number of members have contributed to her campaign, including neighboring Congresswoman Kathy Castor, fellow Floridian Debbie Wasserman Schultz, Eric Swalwell of California, and Nikki Budzinski of Illinois.

Earlier this week, Cuban joined me on Impolitic With John Heilemann to discuss his view of the race, Elon Musk’s strange-if-predictable peregrination into Trumpworld, why he likens Harris to a startup C.E.O., how her policy proposals might benefit entrepreneurs, Trump’s remarkable economic illiteracy, and much, much more. The following conversation, which has been excerpted from the podcast, has been lightly edited.

Mark Cuban: There’s two Elon Musks. You have the amazing entrepreneur, who I have so much respect for, who literally could go down as one, if not the greatest entrepreneur of our generation. So, he deserves his props there. Then, there’s Elon Musk the troll—and the troll I don’t have a lot of respect for, because he’s not that good at it. He says stuff that just doesn’t make sense. Good trolls have a little bit of truth in them, and they kind of extend it to areas where you have to question whether or not something could happen. He doesn’t have any kernels of truth in what he says, and so it’s easy to dismiss. He’s just a shitty-ass, lousy troll, and I don’t think it will accomplish anything. Then again, just to be candid—if I’m on Twitter, everybody thinks I’m just a shitty troll for Kamala.

Twitter is a degraded platform now, and I don’t mean just because of Elon. It used to be a real-time source for news for a lot of people in the journalism business, and now it’s almost unusable. Do you find that the platform has become degraded for you as a power user?

For sure. There’s not one post I make where, in the replies, I won’t get an antisemitic comment. And I’m not looking to kick those people out. Let me be clear, I want to know who the idiots and morons are. But the question becomes whether Elon looks at that as a feature or as a bug. Twitter is a conduit to every prime minister and ruler across the world, at least those that have Twitter in their country. And if you’re a politician, you have to be cognizant of what’s happening on there. And the only person who controls the dialogue is Elon Musk, and that’s a powerful position.

That gets us to the question about his support for Trump. How do you explain it? There are people who view it as Elon making a bet that Trump will be the next president, and that he thinks he can control Trump and use him as an instrument. Others say he’s just bought himself incredible access to the most powerful person in the country. Either way, most don’t believe it’s about some belief in MAGA.

It’s definitely not a belief in MAGA. If you watched the podcast they did together, Trump was not even reasonably capable of responding to some of the points that Elon was making, and Elon had to cover for him. It became obvious it wasn’t a meeting of the minds on a policy basis. At the same time, I think Elon is going to be on the long list of people who tried to be the adult in the room, tried to manipulate Trump, and got manipulated himself.

In one of your tweets to Elon that got a lot of attention, you wrote, “There will come a time when you need something from Donald Trump. You think you will have earned the right to ask and receive. You’ve been a loyal, faithful soldier for him. You’ve supported him politically with tens of millions of dollars. Then at the point you need him most, you will find out what so many before you have learned, his loyalty is only to himself.” Have you learned that lesson?

I haven’t learned that lesson personally. I’ve dealt with [Trump] and I’ve talked to him a bunch. We haven’t done any economic business, but we tried to do some things that didn’t work out when he got involved in MMA. I’ve had a love-hate relationship with him, but I’ve never really needed anything from him. But you just have to look at the list—everybody who’s had the pleasure or displeasure of working with him, he’s come out fine and others around him, not so much. Elon is just going to have to learn the hard way.

When it was Trump versus Biden, it made perfect sense that the Silicon Valley folks connected with Trump. Biden wasn’t very accepting of the technology industry and crypto, in particular. Then when it switched to Kamala, they were already so bought in that they had to double down on Trump. I don’t think in their hearts of hearts they truly believe he’s the best candidate.

Did you share the view that Biden’s mental acuity had declined to the point where you weren’t comfortable with the notion of him serving another four years?

I didn’t talk to him that much over the last couple years, but the couple of times I dealt with him, he wasn’t as quick or as sharp, but he wasn’t any less smart, if that makes sense. If you gave him enough time, he’d get to it, but he obviously was slowing down. The worst part is he looked like a walking corpse. You couldn’t package him to make him sellable.

It’s volume. This isn’t just one instance. Go down the list: Trump University, Trump SoHo, Trump Foundation, the loan he gave himself that should have been on his taxes, the Stormy Daniels stuff, etcetera. Recently, he basically condoned short paying hard-working Americans. He’s ripped off hard-working Americans so many different times. No one else can compare.

Is it fair to say your basic thing about Trump is that he doesn’t know shit about business, that he’s economically illiterate? You said recently that it’s like gibberish when he answers questions about economic policy.

The answer is yes. I’m not going to say he’s bad at business across the board, because he is a good salesperson. But operationally, that’s a different beast, and you haven’t seen any operational skills, and that’s reflected in his policies. To make matters worse, he doesn’t understand the impact some of these things have on smaller businesses. And that’s a huge difference between him and Kamala.

Trump and Vance have embraced the idea that the left is responsible for the assassination attempts on Trump. Vance’s argument is that by saying Trump is a threat to democracy, that contributed to an atmosphere of hate that led to these two inexcusable acts of political violence. Do you think he has a point?

I don’t get to that conclusion, particularly with Kamala. To her credit, she’s criticized J.D. and Donald, but nobody else. You don’t hear her talking about Republicans, Trump voters, or Trump fans. She’s specific in her criticisms. Otherwise, she tries to stay relatively positive. Now, contrast that with the obvious: They’re eating cats and dogs and we’re going to deport everybody on day one, and I hate Taylor Swift, and I hate this person… Trump is hateful and he sends that message.

Many people are worried that when we get to November, especially if Trump loses, we’re going to see some bad shit happen. They’re kind of priming the pump for civil war or some version of that. Do you worry about that?

I don’t worry so much about it happening in real time, because that hate has already been there, and it’s not going to be anything new. Whether or not him losing the election would trigger a violent response, I don’t know. I don’t think so. If there’s a violent response if he loses, then now he’s eligible, if you will, to go to jail. All these criminal proceedings will go forward. In 2016 and to a certain extent 2020, I thought it was valid to say the Trump supporters were the silent majority. I don’t think that’s the case anymore. One of the byproducts of Twitter and Elon is that Trump supporters are no longer silent, whatever percentage they are.

I just knew some of the people involved. People would ask me about politics and who I supported and what was going on. The only time they’ve actually set interviews for me was when I was in Pittsburgh during her economic speech. The others were just like this one—you reached out to me, I like you, and I’m like, Let’s do a podcast. The Harris campaign had nothing to do with it, and I don’t let them give me talking points.

You said she’s the only candidate in “founder mode.” Say more about that.

“Founder mode” means, you start a company and it just consumes you. That’s all you think about all day, every day, trying to make your customers happy, trying to do the right thing, trying to win the battles you’re in. It’s not about going out and raising money, it’s about figuring out how to run your company the best possible way. Kamala is focused on finding the best ways to support the American people. It’s not the Democratic Party that’s running this campaign, it’s Kamala Harris, and that’s critically important—that’s founder mode. And the proof is in the results. The day she took over for Biden as the de facto nominee, her favorables were negative. Here we are, 60 to 70 days later, and in the worst case, it’s neck-and-neck. In many cases she’s ahead.

As she’s rolled out her economic program, if you’re making the case that she’s more pro-business than Donald Trump, what specifically do you point to?

She focuses on small businesses first. She focuses on entrepreneurs first. She understands that starting a business is scary, and it means you have to turn your back on what you’ve always done your entire life and take a leap. She understands that’s the American dream. And she wants to bring people together, because when you’re starting a company, if it’s just you, you have to be able to connect to your customers as you start adding employees. You want that stability, you want that calmness, and she projects that. She talks about the Hispanic community; she talks about the Black community; she talks about the L.G.B.T.Q. community. And the number of businesses these communities are starting is growing more rapidly than those from people who look like me.

You’ve endorsed the media strategy that Kamala is pursuing, which is not giving interviews to The Washington Post, The Wall Street Journal, and The New York Times, but platforms like Call Her Daddy and All the Smoke. She went on Howard Stern, which is a brilliant move. Why do you think this is the right strategy?

Whenever you create a strategy for anything, you’ve got to know what the goal is. And the goal is to win the election, period, end of story. You don’t get brownie points for how many newspaper interviews you did. No one looks back to candidates who’ve lost and said, Look at the interviews they did. In her case, it’s about how to reach the most undecided voters who can come your way and get them to vote. And today, with Gen Z in particular, podcasts are the primary communication tool. It’s like marketing a product: You just go where the buyers are. It’s really simple stuff.

Kamala is crushing it with women, but she’s not doing that well with men; Trump is doing better. Why do you think that she, in particular, and Democrats, more generally, have such a hard time with young men especially?

The answer is easy. Young men consume social media more than anybody, and they’re driven by memes. It’s a meme life, and Donald Trump is a meme candidate. You’ve got Donald Trump, who’s been on social media for the last seven years, when social media was truly relevant. Those algorithms are picking up Donald Trump signals and feeding them to young men. On the flip side, women are getting more Kamala on their social feeds because of the algorithm. This is a meme generation; they don’t learn and consume the way prior generations did.