Hey folks,

This week, I’m sending you a bonus edition of this private email to introduce you more fully to one of my colleagues here at Puck: Tara Palmeri. Tara joined us this spring to cover the real intrigue inside D.C.—from the Hill to K Street to the Post—and writes a fantastic biweekly column called The Washington Mall that you should sign up for here.

Some of the Washington and Silicon Valley characters discussed in our back-and-forth today include Ron DeSantis, Joe Lonsdale, Larry Ellison, Eric Greitens, Blake Masters, Mark Halperin, and Kirsten Gillibrand. It’s also a reminder that as a subscriber to Puck, you’re getting the work of a dozen or so authors in our newsroom, including me and Tara. And much more to come.

Teddy Schleifer: I don’t want to say this is quite a Shakeperean tale of unrequited love, but it does feel, at least for the moment, that the G.O.P. donor establishment loves DeSantis more than DeSantis loves them. But hey, every romance has imbalances from time to time, and the governor could do a better job of glad-handing and back-slapping. It came up in nearly every conversation for my piece. It’s not that there is some fundamental fissure between DeSantis and big donors per se—it’s just that DeSantis is universally described as a somewhat awkward guy, without the Bill Clinton charm or social graces. The good news is that he can work on that, no? Obviously it matters not just for donors, but for, you know, voters too.

One G.O.P. source I was talking to argued that just because DeSantis is the donor favorite today doesn’t necessarily mean that Republican heavyweights will ultimately consolidate around him next year. By then, essentially, there will be other credible non-Trump rivals for Wall Street and Silicon Valley kings. Tell me, Tara, even if the money was there, are you a buyer or a seller of the Tim Scotts and Tom Cottons of the world in a competitive primary? I’m a seller.

Tara: It’s hard to build hype for your presidency from the Senate. You basically have to rely on your oratory skills to tell your story, because legislation doesn’t get you a ton of national attention. Americans generally hate Congress and think everyone there is useless. That gives an early advantage to governors that already have a bully pulpit, their own press corp, and the ability to use their state as a model for their presidency. Of course, it helps to have charisma, too. (Remember President Scott Walker?) DeSantis has deftly handled his build-in advantages so far, using his Florida governor’s mansion to pick fights that get national attention over masking, vaccine mandates, sex education in schools, and his beef with Disney. The real question is how he performs on the stump and how he stacks up on the debate stage next to a Cotton or a Scott… or next to Donald Trump.

Scott’s an interesting character. America doesn’t really know him yet, even though he delivered the 2021 rebuttal to the State of the Union. People in South Carolina remember his powerful speech after his police reform bill tanked. For what it’s worth, Barack Obama wasn’t able to differentiate himself as a junior senator from Illinois either, but he was an incredible orator, had a unique message of hope, and was a transformational candidate. Even though Scott is an above-average speaker, he would not be running as America’s first Black president, unlike Obama. Still, there’s definitely more enthusiasm around Scott than someone like Cotton, in part because he has an incredible story of being a young Black teenager growing up in a single parent household. He certainly has a much more optimistic message than Trump, who is so focused on 2020 rather than the future.

Scott has also raised a ton of cash—$42 million, the third most of any Senate candidate this cycle, even though he’s in a safe seat in South Carolina. As you reported, his outside group received some $25 million over the years from Larry Ellison. And instead of hoarding that money, Scott has been notably strategic, using it to shoot ads for other Senate candidates, build allies, and introduce himself to the rest of America.

Now, money isn’t everything. I checked in with one top G.O.P. donor/bundler who sort of poured cold water on the whole idea telling me: “As Rand Paul and Chris Christie were to 2016, so are Tom and Tim to 2024. They are champions for our cause. We love what they say and how they say it. But neither has the ‘It’ factor for the Oval. Our times require a warrior—not a wonk.”

But tell me, besides Ellison, who else is shaping up to be among the top Republican donors this cycle? Who’s still loyal to Trump and who is flirting with alternatives?

Teddy: This is the first election in seven years that establishment Republican contributors can pretend—just for the moment, and somewhat delusionally—that Trump isn’t in the picture. And while I mainly focus on the tech donor set, I think you’re seeing the traditional mainstream donor universe engage more like they did in, say, 2014, the last election cycle before Trump. Chuck Schwab. Steve Schwarzman. Bernie Marcus. Paul Singer. You know the types. New F.E.C. filings over the last week show that they’re among the big donors to the Senate Leadership Fund and the Congressional Leadership Fund, the super PACs tied to Mitch McConnell and Kevin McCarthy, just as they were in the pre-Trump era. Ken Griffin, the Citadel hedge fund chief in Chicago, is especially ubiquitous these days—including putting $5 million behind DeSantis.

The difference in these times, though, is the rise of the purely Trump-inspired donors: People like the reclusive Wyoming billionaire Timothy Mellon, who gave $10 million to the C.L.F. last month. Or, in my neck of the woods, Peter Thiel, who was revealed today to have given $1.5 million more to support Blake Masters in Arizona, bringing Thiel’s spend for Masters now up to a total of $15 million.

That last Blake check has me wondering about whether this new crop of donors on the right can actually produce more extreme candidates. I know the conventional wisdom is that donors are moderating forces, but that’s always struck me as simplistic (for Democrats, too). Masters, buoyed by that P.T. money and the Trump endorsement, is probably going to win the G.O.P. primary in two weeks’ time. But I’ve got to think that he’ll have a harder time winning in a purple state than J.D. Vance, the other Thiel guy, who faces better odds in Ohio. (Though I will say that some of the polling and fundraising data makes me more bearish on J.D. than when I last wrote about this race last month.) Blake already is being pounded by oppo—mostly old speeches and writings, including on CrossFit message boards!—and I imagine the drip will only get worse for him in October when it’s not a G.O.P. primary but a general election with the Senate on the line.

So that’s one example of donors putting the Senate at risk. I suppose the Missouri gubernatorial race, where donors have spun up a last-ditch effort to beat back the problematic Eric Greitens, is a good test of whether these donors can actually be that moderating influence?

Tara: That’s right, you’re starting to see some serious money flow into Missouri. Nebraska Governor and billionaire Pete Ricketts is throwing down millions in part to highlight exactly what Greitens is alleged to have done to his mistress. Vicky Hartzler, who had the endorsement of Josh Hawley and others, was ascendent and seen as a viable alternative to Greitens—a Trafalgar poll actually gave her a slight lead on Greitens—before Trump shot her down as not MAGA enough. Now rival support will likely coalesce around the state’s attorney general, Eric Schmitt, who was a steady third in the polls. He could use it, as he’s not the most prolific fundraiser. The game-changer in all of this is a Trump endorsement. I’m not sure a blanket of ads against Greitens, paid for by the biggest donors in the G.O.P. in the name of family values, can compete with a Trump endorsement in Missouri.

Teddy: Speaking of the establishment striking back, or trying to strike back, you wrote the other week that even No Labels is thinking they could recruit a credible third-party candidate, yeah?

Tara: They do, and they’ve been able to raise a ton of cash—I reported last month that they’ve raised over $50 million for a single initiative to get their “No Labels” party on the presidential ballot in all 50 states. Their message appeals to Wall Street types who crave stability, which is what they’re promising by supporting relatively moderate candidates such as Joe Manchin, Larry Hogan, and Lisa Murkowski. But everyone in D.C. is very distrustful of No Labels. Democrats say they’re a cover for Republicans, since they considered supporting a primary challenge to Nancy Pelosi. Some members of their congressional inprint, the Problems Solvers Caucus, even voted against certifying the 2020 elections. Republicans don’t trust them because C.E.O. Nancy Jacobson and her husband, the former Clinton strategist Mark Penn, are nominally lifelong Democrats. Both parties see No Labels as a massive distraction, and they’re worried about what the group will do with all of that money because they tend to work in secret. When I tried to speak to them about their push to get a “No Labels” party on the ballot, they refused to speak to me. Jacobson said to me, “What’s best for democracy is confidentiality,” after she sent my article to their vast network. Hiring Mark Halperin after his #MeToo scandal didn’t exactly endear them with their colleagues, either.

Of course, the other reason these sorts of groups have lost power in Washington is the rise of small dollar digital donations. No Labels clearly has a hook into the wealthy, but lobbyists and other rich donors are increasingly having to compete with fundraising that’s organized on the internet, driven by social media, and crowdsourced at the national level.

Teddy: I think we’re singing from the same songbook here. At the presidential level, the bundlers and lobbyists who raise money at $2,900-a-pop are losing their juice. The Bush-era structure of, say, a National Finance Committee, stacked with party poobahs and hyper-connectors who were nicknamed Pioneers and Rangers, might have been the best way to raise money in 2000, but today it strikes me as awfully expensive: It requires candidate time and travel. It opens up a campaign to leaks and to bad press. And it’s not the only game in town anymore, as you note. Candidates with natural followings can obviously raise digital money that isn’t cost-free, yes, and carries its own perverse incentives, for sure. But when it works, it works. And if you’re going to be the candidate of big donors, why settle for hard-dollar contributions capped at $2,900 when you can collect $29 million via a super PAC? I know candidates can’t control the messaging of a PAC as you can when the money is in your campaign fund, but I think a smart campaign in 2024 chooses between being the candidate of real small money or real big money—and cuts out the middle money.

Anyway, that’s the vibe out here in the sticks of San Francisco. Tell me Tara, who’s on the radar of the New York’s Democratic donor class right now?

Tara: Everyone here is watching to see whatever Kirsten Gillibrand decides to do in 2024. I’ve reported before that she’s said to be growing bored of the Senate and may be looking to greener pastures in the corporate world rather than stick it out and face a likely primary challenger for her seat. Anybody and everybody will run, including, maybe, Al Franken. New York has a slew of bright young stars waiting in the wings, like Alexandria Ocasio-Cortez, and while she’s been able to raise gobs of cash with her grassroots popularity, freshman Rep. Ritchie Torres from the South Bronx has become the darling of New York donor circles. Ocasio-Cortez has $6 million cash on hand, but Torres is not far behind her with $3.2 million. It’s notable that he’s raising money at fundraisers like those hosted by Upper East Side socialite-designer Shoshanna Lonstein, a trustee of Congregation Emanu-El, and Israeli actress Noa Tishby, whereas Ocasio-Cortez—who wept when she changed her vote from “no” to “present” on funding for the Iron Dome—has pissed off a lot of New York Jews. Now they’re looking at Torres who’s 34, gay, and Black, and isn’t trying to take down the establishment. During his first campaign in 2020 he was sure to play up his pro-Israel credentials, even when he was slammed by progressives. “Fancy people love him,” one New York donor told me recently. “He’s woke in a way that appeals to wealthy people.” Which is what it’s all about in politics, right?