Shanahan’s latest evolution, from Democratic donor to R.F.K. acolyte, began last year with her research into autism and vaccines. (Shanahan, whose daughter is autistic, has said she is not “anti-vax,” but wants more public debate about screening vaccines before they are administered to children.) She had also come into a fair bit of money—her own money, crucially—as a result of her divorce from Brin. In early February, Shanahan donated $4 million to the super PAC behind R.F.K.’s Super Bowl ad—a 30-second, faux-retro spot that had the rest of the Kennedy clan howling with rage. 

But Shanahan’s leap from supporter to financial backer to vice presidential candidate, in the space of just a few months, has left her social circle grasping for answers. The hushed conversation in Silicon Valley today, among those who know her, or thought they knew her, is whether she is ready for prime time—for the opposition research that’s already circulating, the tidal wave of media scrutiny, and for the extraordinary demands of the campaign trail. 

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Knowing Nicole

In person, Shanahan is warm, relaxed, and charismatic, and given to flights of woo-woo philosophizing about health and wellness. She is a regular at Burning Man, and at one point kept pet pigs, according to a person who met them. (Weird pets, I’m sad to report, are somewhat common in tech circles). In many ways, she presents as someone who has climbed her way to the heights of Silicon Valley’s social pecking order but is now a bit unsure about where she fits in. 

Shanahan had a rough childhood in Oakland—her father had a mental illness, and the family often relied on government assistance—but made her way to Seattle for college, then Santa Clara for law school. She has always known how to party, according to people who know her, and was briefly married to Jeremy Kranz, nowadays a prominent venture capitalist, whom she divorced in 2014, around the time she founded a patent-law startup. Shanahan met Sergey Brin that same year, at the Wanderlust yoga festival in Lake Tahoe.

Her marriage to Brin changed everything. Suddenly, she was not just Nicole, but Silicon Valley royalty, an essential part of Bayshore Global Management, Brin’s sprawling family office—a $100 billion fiefdom encompassing superyachts and their staff, estate planners, crafty accountants, executive chefs, and even a SWAT search-and-rescue team. The extreme wealth could be alienating for her, and isolating, in its way. Shanahan connected with a small group of women who were tied to other Silicon Valley billionaires: Julia Milner, the wife of Yuri Milner; Ayesha Thapar, the wife of Nikesh Arora; and Lucy Southworth, the wife of the monkish Larry Page. She’d attend galas—from the Motion Pictures Association in LA, to the Met Gala in NYC, to the Breakthrough Prize in Silicon Valley—always arm-in-arm with Sergey, both dressed to the nines. When Brin made a rare appearance at Google’s summer camp in Sicily, I’m told, Shanahan came, too.

Like many people who marry into extraordinary fortune, Shanahan dove head-first into philanthropy, founding a nonprofit called Bia-Echo. She was acutely sensitive to the ways in which the world of big-money philanthropy could be gendered, and how male billionaires tended to ignore women’s causes, like Planned Parenthood and abortion access, both of which she funded. Shanahan, who had struggled to have a child, also poured money into fertility-extension research, a field that might have been off the radar of the average male philanthropist. She got so hands-on that she effectively ousted the top aides at Bia Echo, I’m told, so she could do it herself (she has some help from Chloe Cockburn, a former aide to Dustin Moskovitz).

Shanahan wanted to do politics, too, if she could generally avoid the spotlight. Her husband, after all, was a magnet for attention, so she and Brin, advised by a former Obama official, Collin Burton, intentionally gravitated toward dark-money 501(c)4s: “a ton,” said a person familiar with their giving, “all under the radar.” Among the few causes Shanahan publicly financed were several ballot initiatives focused on criminal-justice reform, though she would later turn on several of the movement’s ultra-progressive practitioners, such as San Francisco district attorney Chesa Boudin, whose recall she supported. Shanahan was particularly drawn to cross-partisan causes, like reproductive health or criminal justice reform, more broadly. “I’d rather put my money into the thing that you want to solve rather than paying for TV ads and further dividing the country,” she told me in mid-2022. “I don’t want to fund anything that’s polarizing, because there’s so much work to be done that is apolitical.” Shanahan was often excited to fund anti-Trump efforts, a source told me, but sometimes bristled at more explicitly progressive funding proposals.

At the time, Democrats in Silicon Valley were fixated on Shanahan as the next big thing in progressive politics, especially when she was attached to the Sergey fortune. (Two years ago, I referred to her as “the next MacKenzie Scott.”) During the last presidential election, for example, Shanahan and her team at Bayshore reached out to several Democratic presidential candidates to see if they’d meet with her to discuss criminal justice reform, a source told me. But those hopes for Shanahan apparently misunderstood her politics. Over the past week, some of those same liberals have expressed to me their furious sense of betrayal by Shanahan, who they perceived as a progressive ally. In 2019, after all, Shanahan had excitedly co-hosted an event for Pete Buttigieg. Now, a full election cycle later, former Buttigieg operatives have organized an oppo call to take her and R.F.K. down.

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The R.F.K. Rabbit Hole

Shanahan, by all accounts a true believer in Kennedy’s third-party cause, discovered the candidate in a now familiar, almost stereotypical way. According to associates, her evolution away from the political mainstream began while researching her daughter’s autism diagnosis. Shanahan was consumed, she has said, spending more than half of her time investigating the condition and talking to scientists. (Connections between vaccines and autism have been repeatedly debunked.) In the end, her curiosity led her to Kennedy, an environmental lawyer now better known as one of the nation’s leading anti-vaccine advocates. 

There was also her divorce, finalized last year, which gave her a checkbook without interference from Bayshore. In mid-2022, she started a new family office, Planeta Management, which gave the $4 million check to the super PAC. And presumably that’s just a taste of the capital Shanahan has at her disposal. The terms of her divorce settlement with Brin haven’t been made public, but as I’ve reported, some R.F.K. allies had been told cryptically in recent weeks that they wouldn’t have to worry about money anymore—intimating the arrival of some serious cash. Presidential and vice presidential candidates aren’t limited in their self-funding.

Still, there’s the question that everyone is asking: How much capital does she really have to commit to their joint bid? My sense, for what it’s worth, is that I’d be surprised if she put in $50 million—but wouldn’t be surprised by $15 million. Perhaps that’s why a Kennedy campaign aide called me late Monday night to ask if her divorce settlement was a public document.

The money, of course, also accelerated her entry into Kennedy’s inner circle. Shanahan did not know Kennedy well before she made her first donation in mid-2023, I’m told by a source familiar with the relationship. But over the course of that year, Shanahan—enticed by R.F.K.’s appearances on various podcasts—began making connections with Kennedyworld, which was elated to welcome a hyper-connected Silicon Valley impresario.

Joining the ticket, though, was something else entirely—a late-breaking development, I’m told, and not a job that Shanahan had sought out. A few weeks ago, Shanahan began letting some outside groups know that she wanted to put up some boundaries with them, a comment that struck some R.F.K. allies as pretty interesting. And then, over the last few days, as she followed Kennedy around Malibu art studios, Shanahan began letting a small group of people know that she was about to take the gig, I’m told.

It was “actually a really big personal decision for her,” said the source familiar with the Shanahan-Kennedy courtship. “Because she is not a professional politician, because she is someone who is very affluent, she does have a life that is very comfortable that she would be sacrificing.” In private conversations with friends over the last few weeks, I’m told, Shanahan has strongly suggested that she’ll make a major donation to the R.F.K. campaign, but has resisted saying that explicitly.

Of course, outside of the money she can inject into Kennedy’s expensive ballot-access efforts, Shanahan also has her own appeal: She is a younger, half-Asian woman who cuts a contrast with the political establishment that Kennedy is running against. She is no Aaron Rodgers, but she has talent, as anyone watching her announcement speech could surmise. 

Now, life is about to get messy in the political thunderdome. While Shanahan was largely unfazed by headlines about her divorce, which received perfunctory coverage, she was rattled by a Wall Street Journal story later in 2022 that loosely pinned an alleged potential romantic encounter with Musk as the reason for her divorce from Sergey. At the time, Shanahan hired star litigator Bryan Freedman, who threatened defamation lawsuits.

Sure, she and Elon definitely have partied together, I can confirm, even as she became more of a Silicon Valley celeb. But it never felt like the Journal crossed all the T’s on the story, which was largely (depending on your level of technicality) denied by both Musk and Shanahan. Shanahan felt like her life was absolutely sexualized. “My career has been based on academic and intellectual credibility, and I was being shamed internationally for being a cheater,” Shanahan told People in her coming-out interview last year. “To be known because of a sexual act is one of the most humiliating things… it was utterly debilitating.” (The Journal says it is “confident in our sourcing, and we stand by our reporting.”)

Shanahan said that she is not a “public person” and has tried to keep the focus on her work. It’s “certainly not a love of power,” an associate of Nicole’s told me when I asked why they thought she’s doing this. “I don’t take her as someone who loves the public eye or is trying to be really important or any of those kinds of things that might motivate people. I think she’s motivated by wanting to make the world better.” And what about the Democratic fear that R.F.K. is merely a spoiler that will effectively elect Trump? Nicole, the associate insisted, is “absolutely not a fan of Trump” and “would not do it” if she thought it helped him. 

Alas, Shanahan has volunteered to sign up for more attacks—the vice-presidency, as the saying goes, is a heartbeat away from the presidency, and Democrats are eager to portray her as some political neophyte not ready to oversee the nuclear codes. There are a lot of Sarah Palin comparisons flowing into my text inbox from partisans. Sure, but saying she’s a heartbeat away from the presidency is actually something of an askew compliment of R.F.K.’s impossibly quixotic bid. Shanahan is smart. Friends just hope she knows what’s coming.