Welcome back to The Stratosphere. I’m Teddy Schleifer.

Tonight, a look at the intersection of Silicon Valley, opposition research, and presidential politics. What is the best way for Democrats to deal with Nicole Shanahan, someone they know all too well? Read on for the debate over whether there is an “off-ramp” to convince her to walk away, along with a scoop about Shanahan’s first investment into the Kennedy campaign since she was chosen as the V.P.

But first… a few names from this week’s new F.E.C. reports that will be of interest to regular readers of The Stratosphere…

• Melinda leans in: Melinda French Gates is continuing her political turn. As I’ve chronicled over the years, Gates and her team at Pivotal Ventures—led by Emily Lockwood and Nicole Bates—are becoming less reluctant to engage in partisan politics as part of a strategy to support female candidates. (Her son, Rory, meanwhile, is diving in head first.) Look no further than the $750,000 that Pivotal gave in February to Sister District Project, one of her biggest donations ever, or the $18,000 check she cut to a House Democratic group last month.
• Marc floods the zone: Andreessen Horowitz is also spreading money around Washington. The firm gave $250,000 apiece to the main super PACs of House Republicans, Senate Republicans, and Senate Democrats (House Democrats don’t file until the end of the week). Stratosphere readers are already familiar with the venture firm’s new campaign-finance offensive, as well as its new hard-dollar PAC, Keep Startups in America, whose F.E.C. filing confirms a number of details I’ve reported.
• David vs. Goliath: Larry Ellison is backing Trump this cycle and pushing him to choose Tim Scott as his number two. But what about Larry’s son, David, who is working with his father to land Paramount? The apple seems to have fallen far from the tree. Earlier this year, David Ellison cut the legal super-max check ($929,600) to the Biden Victory Fund, per a new filing, his first major political donation ever. After all, David once told Kara Swisher that he is a “socially liberal person,” but also that “it is very easy to say that everybody in my family believes it was a free and fair election, and accepts the results of the election.”
• Moskovitz’s largesse: Speaking of the venerated super-max check… Dustin Moskovitz, a few weeks after meeting Joe Biden for a private sit-down at the Fairmont Hotel, did indeed super-max out to the Biden Victory Fund.

These flashpoints expose one burgeoning disagreement among the Democratic operatives and allied donors who have spent the past year focused on kneecapping No Labels, and who are now ready to turn their fire on Kennedy. This crew—50-strong and representing entities such as Third Way, MoveOn, The Lincoln Project, American Bridge, and wealthy benefactors like Reid Hoffman—generally liked collaborating to defang a third-party opponent, and many involved felt they’d developed an effective division of labor along the way. Kennedy, many of them fear, could pose an even greater threat, especially with key Democratic constituencies such as Black voters in Michigan or Hispanic voters in Nevada. The Biden team is now closely coordinating with this loose federation, setting up a new super PAC—Clear Choice, funded initially by Silicon Valley players including Hoffman and Ron Conway—intended to manage the operation among these diverse outside groups.

This anti-R.F.K. coalition is now locked in an interesting debate over how cruelly to nuke someone who was, until recently, one of their own. In particular, according to sources familiar with the conversations, two competing philosophies have developed. One advocates for conventionally attacking the 38-year-old centimillionaire and political neophyte, as if she were Elise Stefanik or some other putative Trump V.P. pick. “I’m thinking she’s lived in rarefied air for so long she’ll have to feel the awfulness [of the attacks] before she believes it,” said Reed Galen, a co-founder of The Lincoln Project.

The other, more counterintuitive approach, is to hold fire and pursue what multiple Democrats have described to me as an “off-ramp”—the idea, as unrealistic as it may sound, that trusted messengers could privately persuade Shanahan to extricate herself from Kennedy if she saw enough data depicting Kennedy as a spoilsport. “The way to get her is through peers,” said one person familiar with the dynamic. “It’s not pounding her and calling her a monster.”

This group of operatives has also been at odds over how much attention to even bestow on Shanahan. She may be inexperienced, but unlike a Sarah Palin-type, she is far less controversial than the guy on the top of the ticket. Also, people don’t tend to care about third-party running mates in general. (Quick, can you name Jill Stein’s running mate in 2016?) There is oppo being gathered and circulated, yes, but no “research book” just yet. For now, donors haven’t funded a Shanahan-specific project.

In the meantime, some friends of Shanahan have gotten calls from Democratic operatives to feel them out on the off-ramp approach. During these conversations, the partisans have tried to suss out how she thinks and test arguments that might (or might not) work. Some Democrats involved in the anti-R.F.K. conversations claim they have informants in her inner circle—unclear if that’s true, but it’s what they believe—who could impress upon Shanahan that she is part of a spoiler campaign, and it’s time to abandon ship. Other Democrats involved in the talks see this idea as pathetically naive. Indeed, over the last few weeks, I’m told, Shanahan has regularly had tense conversations with some agitated friends who have argued to her that she is a Biden spoiler and proposed the “off-ramp”; she has pushed back that she believes the Kennedy ticket, statistically, takes more votes away from Trump. Those conversations sometimes devolve into a debate with her over who is better: Biden or Trump? Shanahan replies that she genuinely believes Kennedy can win.

Of course, those informants would also be in position to supply embarrassing information about a candidate who was, until recently, a private citizen living in a very confined universe and who hasn’t yet acclimated to the level of scrutiny that she signed up for—that Journal story notwithstanding. Democrats scored a quick hit when they found easily accessible comments Shanahan made last year calling I.V.F. a “lie,” for instance. But that’s just a YouTube search—no donor intel required.

Carville said that he contacted Wojcicki, for instance, because “somebody showed me something” and “I leak a lot of shit.” But he was particularly interested in anything that would make Kennedy-Shanahan look fringe. “The very accurate case against him is he’s a really weird guy. And without being judgmental, the argument with her is she’s a really weird woman,” Carville told me in his trademark drawl. “Cause Biden might be the most un-weird human being on Earth.”

Indeed, money is also a reason to not go too hard on oppo: Shanahan and Brin maintain cordial relations—they share a young child—and some Democrats worry Sergey could be activated to give to R.F.K. if she is roughed up too much.

Either way, in the three weeks since she joined the Kennedy ticket, Democrats have tried to make Shanahan’s financial role the target of their oppo package, made all the easier by her sparse public profile ever since she was announced as the running mate. Attacking her as someone who essentially bought the number-two slot by promising money for ballot access allows them to undermine Kennedy’s own key message of being a political outsider. And while they’re also looking to portray her as pseudo-conservative, some worry that going after her vaccine skepticism could allow her to talk sympathetically about her autistic child.

It’s not just liberals: conservatives are also poking around too, gingerly for now. Republican dirt-diggers told me they haven’t spent much time or energy on Shanahan yet. (America Rising, the once much-hyped G.O.P. oppo shop, seems to have quietly been hollowed out, by the way.) Like the Democrats, they’re not looking for something salacious from Burning Man or her previously private Instagram or hearsay from her previous marriages, but something politically useful. For Republicans, that means anything that would make the Kennedy ticket more likely to draw votes away from Biden. To wit: A Trump-allied group recently launched a website depicting Kennedy as a “radical liberal” and anti-gun zealot… an attack that prompted Kennedy to claim that Trump “emissaries” had asked him to join their ticket.

Perhaps that defensiveness is why, last Monday, Trump said Shanahan’s name for the first time in a video, calling her out for supporting some particularly controversial liberal district attorneys. “R.F.K. Jr.’s running mate, Nicole Shanahan, is also a very liberal person, but that’s okay—she’s got plenty of money from her ex-husband,” Trump said. Buckle up!