An Obscure Group Hounded Kyrsten Sinema for Years — and It Worked. Is This a Sign of Things to Come?

Officially, Sen. Kyrsten Sinema’s announcement that she wouldn’t seek another Senate term was about a campaign that won’t be happening.

But as the Democrat-turned-Independent senator went before a camera to take herself out of contention, a group of operatives in Arizona and Washington said it felt a lot like the end of a campaign that did happen.

In fact, as they texted back and forth on the Wednesday afternoon of Sinema’s announcement, it was as if they were watching a hated rival’s concession speech on election night.

For years, Sinema was on the receiving end of a relatively unusual political-money phenomenon in the capital’s politics industry: the single-target PAC, an outfit geared towards creating precisely the outcome that became real when the senator announced her exit.

For better or worse, it is a model that probably won’t stay rare for long. And whatever you think of Sinema, the effort against her is also likely to speed up some of the most brutal trends in politics, another way for deep-pocketed donors to further wage permanent war on rivals who might not always make such obvious targets.

Other political committees might beat up on a senator in the name of an issue or to help a particular rival. The Replace Sinema super PAC, by contrast, existed solely to run robust oppo research on, buy ads against, pitch unflattering media stories about and otherwise hound, harry and hector one solitary elected official: Sinema, who had enraged progressives with hostile stances on the filibuster, the minimum wage and Joe Biden’s “Build Back Better” bill, among other things.

And while most senators don’t draw a focused campaign until their election cycle arrives, Sinema was targeted by the super PAC for half of her six years in the upper chamber. Her exit came after years of negative media stories, local ethics complaints, surprisingly on-target journalistic investigations and other misfortunes that tend to happen to pols who become the target of a well-funded group of professional campaign operatives.

“There are a lot of things out there dedicated to taking out Democrats or Republicans, but this was a single mission dedicated to taking out one senator who was uniquely bad,” the outfit’s senior adviser, Sacha Haworth, told me this week. “There probably wasn't a negative headline over the last two years that we didn't have something to do with.”

Now, with Sinema on her way out, the team is taking a victory lap of sorts — Tell Kyrsten I want her to know it was me — and pulling back the curtain on how it went down.

It’s a history that reveals a bit about the unique circumstances of the Arizona senator’s tumble, but may say more about where Washington is headed in the age of networked money, atrophied local media and endless campaigns.

Launched in 2021 as Primary Sinema, the group took a $400,000 donation from Way to Win, a deep-pocketed network of progressive donors. “They came to me and they said, Look, we just think that she needs to be held accountable in a public way,” said TJ Helmstetter, who would become the organization’s executive director.

The goal, Way to Win President Tory Gavito said, was to expose Sinema in the hopes that she’d either change her ways or that some Democrat would come along to challenge her. After a challenger did come along in the form of Rep. Ruben Gallego, prompting Sinema to declare herself an independent, the organization rebranded itself as Replace Sinema and kept doing basically the same thing.

Because federal rules prohibit naming a PAC for a candidate, the formal name was the much less memorable Change for Arizona 2024 PAC. But all the branding, which includes a thumbs-down logo evoking the much-giffed gesture Sinema made as she voted to maintain the filibuster, is Replace Sinema. Way to Win wound up kicking in another $225,000 later, and the group raised $675,000 from just under 18,000 donors on the liberal ActBlue platform.

In the beginning, the backlash had followed a comparatively familiar script: The one where progressives are mad at a moderate who stymied things like expanded voting rights. “There was a feeling of betrayal,” said Luis Avila, a Phoenix community organizer who campaigned for Sinema in 2018 despite his lefty friends’ misgivings about her moderate House record. He eventually became a senior adviser to Replace Sinema.

In Arizona, progressive groups protested her in ways that were pithy and viral, but also part of the general pattern of contemporary politics. After Sinema curtsied theatrically while casting a vote against boosting the minimum wage to $15, activists got thousands of people to send her Venmo requests for $15. Another time, they staged a wine party in front of her Arizona office, a reference to news reports about the senator’s internship at a vineyard owned by a private-equity baron political donor.

What was different in the anti-Sinema campaign was the professional opposition research and messaging to augment in-state activist efforts. Sinema had joined the Senate cultivating a moderate-maverick reputation — one that largely stuck in Washington as she dissented against the Democratic base’s Biden-era agenda. But over the past three-plus years, she’s been the subject of a remarkably long list of sharply negative stories about her luxury spending, private-jet flights, costly limo rides, ties to donors, treatment of staff, security spending, or campaign-funded trips to race in marathons (and stay at Ritz Carltons afterward).

Rather than broadsides against her insufficiently progressive policy views, it was an onslaught that went a long way toward sullying her image as an upstanding public servant.

“I helped unearth old memos,” said Haworth, who came aboard around the time of the party switch. “Or we would do a lot of opposition research into her FEC filings … What we uncovered was, she’s like charging her marathons to the campaign. She’s doing an internship at a winery and they’re doing a fundraiser for her the next day. You can essentially track the headlines between 2022 to now. In 2022, she was this independent dealmaker, and now she is someone who has been painted as an abuser of campaign donations, of taxpayer money to live a luxury lifestyle.”

In one memorable incident, the team noticed that someone on Instagram had tagged Sinema — in Paris. After a bit of digging through campaign finance reports, it emerged that she had spent campaign-donor money on the high-end trip to the French capital right ahead of the 2022 midterms. An epically bad news cycle followed.

Of course, political operatives have steered reporters towards dishy stories forever. Digging through Federal Elections Commission filings isn’t rocket science. But at a time when news organizations are shrinking, and when local media has been particularly hard hit, there are fewer and fewer reporters with the time to do that sort of combing, which makes the role of the oppo pro loom larger.

“Almost none of those [stories] were the result of some reporter thinking organically on their own, ‘Oh I’m going to write a story on Sinema spending on security groups,’” said Jill Normington, the group’s pollster. “It made it harder for her to raise money.”

Looked at one way, this is a troubling development: Imagine some deep-pocketed tycoon funding a group that, say, targets a senator who favors a wealth tax, funding a single-target group that for six years pores through public records to find ostensibly apolitical evidence that the pol is a prima donna or a jerk to staff. In the case of Sinema, the PAC says the goal was to show connections between the luxuries underwritten by her campaign and the policy tilt in favor of the donors who funded that campaign. It’s a distinction that might be lost on some observers — or future political committees.

The research was also all that much easier because so many of Sinema’s sharpest foes were former allies or staffers. It’s one thing to have people who are paid to dig dirt against you. It’s something else entirely when those people are in a position to know just where a lot of the bad stuff is buried.

Haworth, for instance, did a stint on Sinema’s victorious 2018 effort. In late 2022, shortly after she joined the PAC, the Daily Beast published a story about a 37-page internal memo for Sinema staffers. It was a delicious portrait of entitled insiderishness: The senator needed hour-long weekly massages, had to eat protein-dense meals during three specific half-hour periods each day, was widely unavailable after 8:00 p.m., and did not like to fly Southwest Airlines. Haworth said their group had gotten the memo from another fellow staff veteran and leaked it. (At the time, Sinema’s office said they couldn’t verify the document and denied that staff were required to perform personal chores.)

By the time of Sinema’s announcement last week, the super PAC had spent over a million dollars — and the senator essentially had no path to victory.

Sinema’s office declined comment this week, but some of the remaining folks in her political orbit spoke out in ways that echoed the senator’s retirement speech about the bitter tone of our politics.

“This kind of exclusive, explicit oppo campaign is pretty unique as far as I can tell,” John Labombard, a former Sinema communications director who remains close with her, told me. Yet for all its focus on non-ideological themes, he said, the effort was motivated by something ideological and familiar: “It really is discouraging that in a lot of ways my party has become a party of purity tests. I think this particular organization is part cause and part symptom of that larger trend. And I think much of our party’s infrastructure is captured by that purity test mentality.”

Stacy Pearson, an Arizona Democratic strategist and longtime Sinema ally who fears that the progressives behind Replace Sinema will wind up handing her seat to “tinfoil-hat-wearing” Republican Kari Lake, also questioned how novel the opposition work had been. Sinema’s 2018 GOP opponent, she said, also laid into her purported luxury tastes. “The stuff was hiding in plain sight,” she told me. But in the current news environment, even stuff in plain sight can remain well outside the conversation — unless someone spends money to publicize it.

As with an actual winning campaign, there’s a tendency in the case of Sinema’s retirement to overstate the work of the strategists and underappreciate the favorable political winds. In this case, said Rodd McLeod, who managed Sinema’s 2012 campaign for Congress, the most favorable factor of all for Sinema’s foes was the senator’s baffling unwillingness to maintain the coalition that got her elected six years ago.

“There’s people who voted for you who are going to disagree with you on X or Y or Z,” McLeod said. “How do you keep them in the family? This is part of the hard work of sometimes swallowing your pride, sometimes apologizing, sometimes standing up for yourself and saying ‘I made the right call.’ It’s not easy! But she really blew it.”

Against that backdrop, the emergence of an organization like Replace Sinema — however creative and energetic their work turned out to be — may have been as much a symptom of her political problems as the cause of them.

Either way, the proud folks at the PAC say they’ll take it — and, I suspect, so will copycats out to punish some other turncoat (or, for that matter, to soften up an incumbent from the other side). Why raise money to merely spend a year messing with a political rival when you can do it for an entire six-year term? There are a lot of underemployed off-year Washington operatives who could embrace that kind of mission.