The murderer’s row of Democratic operatives working to tank Robert Kennedy Jr.’s third-party presidential bid couldn’t help but roll their eyes last week when Silicon Valley congressman Ro Khanna sent a letter (and planted a story about it) to Nicole Shanahan, whom R.F.K. named as his running mate in late March, asking her to drop off the ticket. Of course, plenty of Democrats complained to me, here was Khanna, a notorious publicity hound, eagerly doing the bidding of the ultra-aggressive MoveOn—a stunt that would only provoke Shanahan to dig in her heels. Then, a few days later, there was the ubiquitous James Carville emailing Anne Wojcicki—the prominent Silicon Valley executive whose ex-husband, Sergey Brin, later married (and divorced) Shanahan—looking for salacious oppo on the candidate’s personal life, a fishing expedition that promptly leaked (without Wojcicki’s name). More complaints…

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.”

A Nicole-Sized Problem

This schism is novel because donors and operatives in tech have unique access to Shanahan: She’s a former Democrat who’s spent the last decade-ish ensconced in Silicon Valley high society as Brin’s partner. And so, over the past few weeks, some Democratic donors have moonlighted as opposition researchers, while others have studied up on high-pressure sales techniques. I’ve been told some of her peers from the benefit circuit have turned against her and are trying to feed gossip and half-baked rumors to operatives in Washington. (The line between opposition research and credible journalism has been getting thinner and thinner, as I reported last year.) Other peers are confident they can leverage that same proximity to talk her off the ledge.

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.”

Shanahan’s $2 Million Investment

Democrats are seeking intel on Shanahan’s financial situation, in particular. Some suspect the Kennedy campaign was running out of money, and that Shanahan’s value to the ticket is her unlimited ability to self-fund. Shanahan and Brin’s divorce was finalized in early 2023, and no one really knows what resources she has to give to the campaign. Does she have $10 million in liquid assets? $100 million? $1 billion? I have learned that Shanahan put $2 million of her fortune directly into the campaign’s bank account at the end of last month, immediately following her announcement. And there’s more to come, I’m told.

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!