Welcome back to The Stratosphere.

I hope you’ve been enjoying some of the work we’ve been co-producing at Puck over the past few weeks, including my recent chat with Tara Palmeri, about the G.O.P.’s donor anxieties and the story I published with Dylan Byers about the alleged Elon-Sergey-Shanahan affair.

Today, I’d like to share the wisdom of a colleague who’s an expert on the conservative movement: Tina Nguyen. Below is the sort of conversation that Tina and I have privately all the time about the characters and the storylines at the intersection of our worlds. Hopefully these collaborations with my partners give you a sense of the breadth of what we write about here.

McCarthy, meanwhile, is hardly a moderate these days. Nevertheless, the two have been friendly for some time—McCarthy often comes across like he is bragging when he brings up “a good friend of mine, Elon Musk.” Elon first donated to McCarthy more than a decade ago and the two talk occasionally. (McCarthy, who represents a Central Valley district far from the Bay Area, has historically had similar relationships with numerous tech leaders, such as Laurene Powell Jobs.) Still, the fact that Elon is headlining a McCarthy confab represents an intriguing evolution in his maturation as a political combatant, and not just playing one online.

Tina Nguyen: I agree that Elon’s policy preferences aren’t entirely clear—for the most part, he seems to support whatever is best for his electric car business. But in the cultural sphere, at least, he represents a broad spectrum of Americans who feel like the extremes of both parties have failed them. He is, in that way, a sort of Joe Rogan figure: mostly liberal instincts, mildly uncomfortable with “wokeness” and seeing his favorite comedians get canceled, thinks that the far-right is extremist and batty, but is generally disengaged from party politics and voting. He’s a much better avatar of that bloc than, say, Andrew Yang and his weird third party ambitions.

Nguyen: If Elon had gone through with his deal to buy Twitter, and if he had replatformed Trump, there’s no question that he would have been embraced by the right as a sort of free speech god-king. Part of the way you gain strength in the eyes of MAGA voters is if you’re perceived to have made some big personal sacrifice in order to stick it to the elites. Trump’s argument to that effect has long been that he could have remained a wealthy billionaire enjoying the high life, but instead decided to fight on behalf of forgotten Americans. I suspect Elon dedicating a chunk of his net worth to a free speech crusade would have had a similar effect.

Sure, he’s managed to save face with conservatives by claiming that Twitter is actually full of bots—the crux of his argument for reneging on his deal to buy the company—which might fly with some portion of the tech-averse MAGA base. But my sense overall is that the G.O.P. is disappointed with Elon for thinking in mere financial terms, rather than transforming himself into the culture war white-knight-martyr that they’d hoped. You get as much out of MAGA as you put in, basically.

Schleifer: There is a certain irony to Trump calling Elon a “bullshit artist” last month, shortly after Elon took considerable heat for pledging to restore Trump to Twitter and erecting a free-speech paradise. Elon’s political travails remind me of Mark Zuckerberg, who also went out of his way to placate the right, which pissed off the left, and then ended up excoriated by Republicans anyway. I guess we’ll see how the Musk-G.O.P. romance twists and turns after Wyoming.

Nguyen: Elon Musk goes to Mars and the G.O.P. is happy to see him go away. It’s both a metaphor and a real thing that might happen if he throws in with DeSantis. Ronny to the moon!

Schleifer: Speaking of DeSantis, here’s a question many of my sources in tech-elite circles would like the answer to: Does he run if Trump does, too? Correct predictions only.

Nguyen: My guess is that DeSantis only runs if he is in a position of strength over Trump, which includes: 1) beating the ever-loving hell out of Trump’s margin of victory in Florida, 2) finding a viable electoral path through the primaries, and 3) whatever happens with all the various investigations into Trump. I’m increasingly concerned, as are many Republicans, about the possibility that elements of Trump’s base turn violent over the current F.B.I. probe and recent raid on Mar-a-Lago.

We’ve already seen several troubling incidents, and Trump himself has called on his people to lower the temperature. I hate to say it, but these are among the conversations G.O.P. insiders are having right now. DeSantis could emerge as the top choice for Republicans who don’t care for the F.B.I rifling through Trump’s basement but draw the line at violent rhetoric (or, god forbid, actual violence) targeting law enforcement.

Schleifer: Yeah, I mean that’s precisely why so many rich donors in Silicon Valley—many of whom never liked Trump to begin with—have gravitated to DeSantis. No doubt that DeSantis will be well-financed if he decides to run against Trump, in part because he’s using his gubernatorial reelection as a vehicle to collect ‘24 funds in plain sight. But I also hear endless whispers from the same donors that DeSantis is borderline awful at the glad-handing and ego-stroking that lubricates these high-dollar hustings. He is the clear choice of the Texas and Florida billionaire set, but so what? You almost wonder whether that could backfire over time, and whether any rusty retail skills might matter more.

Nguyen: So far, DeSantis has managed quite well to balance his populist instinct against his fundraising needs. He’s staged provocative legal battles with Disney and public school teachers over L.G.B.T. issues and “C.R.T.,” and fought both the Trump and Biden administrations over Covid restrictions. He’s also managed to raise more than $100 million, even if it’s true that some donors are tiring of him, especially once they see him up close.

At the same time, there’s a degree to which becoming beholden to donors becomes a political turnoff. Trump won in part because he claimed that he couldn’t be bought. But this gets to the question that so many Republican candidates and donors are wrestling with right now: Is it possible to harness the populist, anti-establishment energy that is fueling the conservative base? Can it be managed by cynical politicians to more traditionally conservative, business-friendly ends? Or do they risk filling Congress with more Marjorie Taylor Greenes?

Schleifer: I think we’ve got to recognize that the populist turn of the party in the Trump era has truly reshaped the high-dollar donor community. The other day I was looking at my phone contacts, scrolling past some of the donors I was bugging for scoops in 2015-2016, and it was remarkable how many of them, due to Trump, are simply not engaged in Republican fundraising at all anymore. The ones who remain range from Trump-tolerant to Trump-avoidant. But I don’t think it’s any different from how many senior Republicans in Washington feel privately—this is the reality of their party now, and it’s adapt or die. And the ones who adapt, like Peter Thiel, have a lot more influence than they did in the Republican Party of Mitt Romney or John McCain.

Schleifer: Break out your tiny violin, Tina, because I believe Peter Thiel is a victim of political pressure, and is at risk of being wildly misunderstood. Everyone, it seems, wants P.T. to be the new G.O.P. kingmaker—except, well, P.T., himself. Democrats are itching to make him a boogeyman—look at how much Tim Ryan, who’s running against Vance in Ohio, talks about Thiel. Senior Republicans also want Thiel to be a force, to fill the high-dollar vacuum left by the deaths of Sheldon Adelson, Foster Friess, and David Koch. And, of course, the media wants Thiel to be a kingmaker too, because, well, it’s just a damn good story.

The less titillating reality, as I’ve tried to honor in my reporting, is that Thiel cares a lot about Vance and Masters, but is less interested in turning American politics into a game of Risk, where he weighs in on various primaries around the country routinely. Blake and J.D., if elected (and one of them probably will be), give Thiel all the foothold he needs to be taken seriously in future Senate campaigns. Yes, Thiel’s ring will probably need to be kissed in the ‘24 primary, too. But I don’t believe Thiel is going to hire tons of muscle like the Kochs did.

Nguyen: It’s funny, because to me, Thiel’s impact on the right is measured more in the intellectual and philosophical realm: trying to back magazines, journals, institutes and other soft power vehicles to promote a specific, nationalist worldview. He was part of the team that funded American Greatness and the Rockbridge Network (which you’ve written about); he’s got this informal affiliation with the Intellectual Dark Web and frequently speaks at conservative and libertarian events. For these outsider academic and activist groups, there’s a sexiness to having a tech billionaire on your side.

Schleifer: Yeah, I was going to bug you about that. It’s been fascinating to observe lefty donors steal ideas from G.O.P. donors over the last several years. Republicans were the first to innovate in the Citizens United era, but the Democrats have since caught up in scale and strategy, including funding “independent” media. Is that a lesson they should take from conservatives? You have an amazing perspective here as someone who was employed in conservative media. Can you tell me, from a political investor’s P.O.V., has the tactic of building out a conservative media ecosystem actually succeeded in propagating the worldview of their investors?

Nguyen: It’s funny, the complaint I hear more often on the right is actually that conservative media has too many activists and opinion writers, and not enough real journalism. Granted, these trends go back years, when activist groups like the Leadership Institute, Young America’s Foundation, the Collegiate Network, the Institute for Humane Studies (where I got my start), and a number of other outlets trained conservatives to enter the media industry. That inadvertently led to a situation where right-wing news outlets have less impact beyond their superfans, because the ideology takes precedence over news-gathering, as even their most dedicated consumers recognize. If they wanted to build an echo chamber and capture an audience that reflexively thinks that any other outlet is biased, well, mission accomplished. And it can be lucrative, as the team behind the Daily Wire could tell you. But if the point is to spread their politics outside their core audience and sway non-conservatives… that hasn’t worked out as well.