The Rise and Fall of the Never Trump Machine By Hayden Ludwig
https://tomklingenstein.com/the-rise-and-fall-of-the-never-trump-machine/
Kamala Harris and the Democrat establishment may have blown over a billion dollars to lose the 2024 election, but it’s their Never Trump allies most likely facing oblivion after President Donald Trump’s historic victory.
If so, good riddance.
But don’t be too quick to count out the likes of Bill Kristol, Charlie Sykes, Liz Cheney, or the operatives behind groups such as the Lincoln Project who helped organize the Left’s 2020 campaign to oust Trump from the White House. They may still play a role in the second Trump “resistance” beginning in January — if Democrats will let them.
At the heart of that effort is a set of insider groups — niche publications like The Bulwark and think tanks for exiled ex-conservatives like the Niskanen Center — that led the old GOP’s exiles into the wilderness, forged a powerful political force for undermining Trump’s Republican base, then pledged itself fully to the Harris campaign and the regime that supported it. At each step of the way, these “principled conservatives” grew tangibly more liberal, more hawkish on America’s forever wars, and more fanatical in their hatred of the America First movement.
By November 2024, however, Never Trump Inc. ended up friendless and defeated. Here’s the story of their rise and fall.
The Nonprofit Revolving Door
There’s no understanding the Never Trump cabal without reading its flagship commentary website: The Bulwark.
The site operates as a hub for all things anti-Trump, charting the Right’s descent (as they see it) into knuckle-dragging white supremacy, authoritarianism, and subservience to Moscow. It’s a refuge for bitter Beltway relics of the Bush-Romney establishment who smugly cast themselves as the true heirs of Ronald Reagan, rather than out-of-touch elites more aligned with Nancy Pelosi and Joe Biden than the Gipper.
The Bulwark was founded by a handful of once-influential Beltway writers, most famously Bill Kristol, son of the late Irving Kristol and editor of the now-defunct Weekly Standard. But his co-founders, ex-Wisconsin radio host Charlie Sykes, who left the Bulwark for MSNBC in February, and Sarah Longwell, a political consultant and one-time chair of the LGBT group Log Cabin Republicans, are just as critical to The Bulwark’s evolution into Never Trump’s lodestar.
With Kristol and Longwell at the helm, The Bulwark grew into the Kremlin for an organized network of anti-Trump forces that developed across Trump’s first term. In a few short years, they transformed the jumbled anti-Trump forces into an eight-figure political ad machine for boosting Democrats, funded overwhelmingly by mega-donors on the Left.
But none of that would have been possible without support from a lesser-known D.C. group, the Niskanen Center, which set the stage for what became The Bulwark.
Though it’s hardly a household name, the Niskanen Center is infamous in conservative Beltway circles as a gun-for-hire for Big Green activists. The think tank was born from a 2014 row within the libertarian Cato Institute over environmental policy led by then-Cato vice president Jerry Taylor. Taylor, who spent 20 years fighting as Cato’s “lead climate denier,” became convinced of the global warming threat and jumped ship to found his own left-leaning libertarian organization.
(The obscure name was Taylor’s way of flipping the middle finger to Cato. It comes from legendary Cato co-founder William Niskanen, Reagan’s economic advisor and far from a global warmer, whose 2011 death sparked high drama within D.C. libertarianism and precipitated Taylor’s split from the flagship of the movement.)
The Niskanen Center’s first project was selling conservatives on the merits of a carbon tax, a tax levied on companies’ carbon dioxide emissions to punish them into reducing their CO2 footprint. In 2019, when I spent significant time exposing the growing coalition of “eco-Right” groups — all funded by liberals — the carbon tax push emerged as a dire and underreported threat to the Republican Party. The eco-Right gained support in Congress from squishy Republican congressmen such as Reps. Carlos Curbelo (FL) and Brian Fitzpatrick (PA), who tried to normalize global warming and carbon taxes as conservative issues. If successful, they could have split the fragile GOP and given Democrats a powerful electoral edge. They lost that fight, while Curbelo and Fitzpatrick lost their seats.
As time went on, Niskanen’s eco-proposals grew more extreme. At one point, Taylor — writing with the Sierra Club’s former climate counsel — proposed fining companies for “increas[ing] the number and severity of wildfires, droughts, and flash flooding,” which they blamed on climate change. For justification he cited James Hansen, Obama’s radical NASA director who told Congress in 2008 that fossil fuel company “CEOs should be tried for high crimes against humanity and nature.” At the same time, Taylor opened a public feud with his own brother, James, who became head of the climate-skeptic Heartland Institute.
Money immediately began pumping into the new organization from the Left. I’ve traced six- to eight-figure grants from major “green” funders: the Hewlett and Packard Foundations; League of Conservation Voters; the multi-billion-dollar Arabella Advisors network; Arnold Ventures, bankrolled by ex-Enron billionaire John Arnold; Carnegie Corporation (despite its name, a foundation); the Joyce Foundation, whose board once included Sen. Barack Obama; eBay founder Pierre Omidyar; and arch-progressive George Soros.
Soros, in particular, played an influential role in the Niskanen Center’s retreat from libertarianism to leftism and the development of its positions on far more than climate change.
In 2019, Niskanen announced it was “leav[ing] ideology behind” for a new vision of an “open society” at the same time it was quietly receiving millions of dollars from Soros’s Open Society Foundations. The phrase isn’t a coincidence; in both cases it’s taken from the writings of Karl Popper, an ex-Marxist philosopher whose definition of libertarianism hinged on social engineering programs. Soros credits Popper for inspiring his globalist attitude “that no philosophy or ideology is the final arbiter of truth.” So, too, does Niskanen credit Popper in describing itself as a band of “globalists who share progressives’ desire to robustly address economic and social inequality.”
The Niskanen Center’s reputation as a chisel to peel conservative voters away from the Republican Party has diminished along with the rest of the eco-Right (and climate fearmongering in general). Jerry Taylor himself left Niskanen in 2021 amid police reports that he’d drunkenly strangled and slapped his wife, to which he pleaded guilty. But at its peak the center was a vital hub for connecting Kristol and others who would become the masters of Never Trump Inc.
DDT for Democracy
Shortly after Donald Trump took office, Jerry Taylor invited distraught neocons to a series of quasi-secret gatherings he deemed “Meetings of the Concerned.”
Besides Kristol and Longwell, the collection included George Conway (former husband of Kellyanne), Max Boot of the Council on Foreign Relations, and the future Lincoln Project founders Steve Schmidt and Rick Wilson. Those desperate first meetings between Longwell and Kristol resulted in a trifecta of new groups launched in January 2018 under the umbrella Defending Democracy Together, which bears the delightful acronym “DDT.”
Structurally, DDT consists of a 501(c)(3) “charitable” arm, which publishes The Bulwark; a 501(c)(4) arm that houses their attack group, Republicans for the Rule of Law; and the Republican Accountability PAC, variously branded “Republican Voters Against Trump” or simply “Republican Accountability.” All share overlapping leadership and major donors.
Their goal is the same: humble the Republican Party into submission by helping Democrats beat Trump. Lick him hard enough and conservatives will soon abandon MAGA altogether. Then Kristol et al. can retake their rightful place at the head of the GOP, and all will be well in Washington.
So the theory goes. In reality, they quickly discovered the pool of anti-Trump conservative donors is trifling and has only shrunk since 2016. Hedge fund billionaire Paul Singer, for instance, spent heavily to stop Trump’s nomination in 2016 — even engaging the now-notorious firm Fusion GPS — but later changed his mind, contributing $5 million to a pro-Trump super PAC in 2024.
So DDT did the predictable: It cozied up to mega-donors on the Left.
When I pressed Longwell in 2020 for her organization’s donors, she told me DDT is funded by “all sorts of people who care about democracy and the rule of law.”
One of those selfless donors is eBay founder Pierre Omidyar, whose Democracy Fund bankrolled Democrats’ mail-in ballot groups in the 2020 election. Omidyar himself has quietly become one of the Left’s top funders in recent years. His grants to DDT were specifically earmarked for DDT’s Republicans for the Rule of Law project to sway Republican voters against Trump.
DDT is heavily funded by the Hewlett Foundation, of Hewlett-Packard fame, a key funder of pseudo-conservative groups created to infiltrate the GOP. The foundation is also a top donor to the Niskanen Center, for instance, as well as Stand Up Republic, an advocacy group created by 2016 Never Trump presidential candidate Evan McMullin.
DDT co-founder Charlie Sykes is on Stand Up Republic’s board and advises Omidyar’s Democracy Fund.
Another donor: America Future Republic, bankrolled by LinkedIn founder and Trump foe Reid Hoffman. Hoffman’s group funded E. Jean Carroll’s 2023 lawsuit alleging Trump had raped the former New York Magazine writer, who lied that no one was paying her legal fees.
Another $1 million grant came from the Pacific Environmental Coalition, which trains eco-activists to push radical environmental policies. Its grant to DDT is tagged for “support[ing] Republican Voters Against Trump initiative.”
The John Pritzker Family Fund gave DDT $225,000 in 2019. John Pritzker is heir to the ultra-wealthy Chicago family whose billions came from the Hyatt Hotels Corporation. His nephew is the Democratic governor of Illinois, J.B. Pritzker, who leads the newly announced Governors Safeguarding Democracy effort to “Trump-proof” blue states.
And millions more in DDT cash came from the Sixteen Thirty Fund, part of the multi-billion-dollar “dark money” network run by Arabella Advisors. The Arabella network is Democrats’ secret weapon that funnels vast sums of money into political groups they believe will defeat Republicans and ensure a permanent Democrat majority in Washington. Sixteen Thirty Fund’s $10 million grant in 2020 remains the single largest known grant to DDT.
“Democracy Doesn’t Defend Itself”
At launch, DDT shared the address of Berman & Co., a prominent center-right political consulting firm where Longwell worked as a partner and senior vice president until she launched her own consultancy, Longwell Partners, in December 2019 with a handful of Berman staffers. “Democracy doesn’t defend itself” is the motto on her consultancy’s website, which says it caters to groups building a “bipartisan, pro-democracy coalition.”
As expected, there are deep ties between Longwell Partners and Republican Accountability PAC, which is housed at the firm’s cushy downtown D.C. office space on Vermont Ave. Sarah Longwell is listed as the PAC’s treasurer in FEC filings. Patrick Stoltzfus, the firm’s accountant, is its custodian of records. DDT’s charitable arm similarly lists Longwell Partners as its “management company” in its 2022 IRS Form 990 disclosure.
In fact, DDT and the Republican Accountability PAC are the only clients of the firm listed in 2024 FEC filings. A PAC filing from 2022 similarly shows an unpaid debt of $42,000 owed to Longwell Partners. The only other known clients include Wyoming Rep. Liz Cheney’s 2022 reelection campaign, which she lost 66–29%, and the Democrat PAC Reclaim Our Party, which spent $172,000 battling Trump in 2020.
Nine days after the January 6, 2021, U.S. Capitol riot, Republican Accountability PAC, DDT, and the Lincoln Project announced a joint plan to raise $50 million for “principled Republicans” in Congress “who would do the right thing and hold Trump accountable for inciting an attack on the U.S. Capitol.” The funds were meant to support primary challenges to Republicans who voted against impeaching the outgoing president on January 13.
Of that $50 million raised — $37 million of it just in 2024 — $4.6 million went to Longwell Partners for staffing, strategy and consulting, polling, and TV advertising fees. In other words, Longwell’s firm created its own top client — a classic Beltway move.
Most of the rest, totaling $41 million, went to independent expenditures attacking Republicans and boosting Democrats. It paid for anti-Trump and pro-Harris billboards, get-out-the-vote text messages, and ads on YouTube and cable TV. FEC filings report 1,041 individual expenditures against Trump alone in 2024.
Virtually all of this cash came from left-wing donors. Netflix chairman Reed Hastings is the PAC’s top donor; filings show the $6.9 million he gave the PAC was his largest single contribution in the 2024 election cycle.
LinkedIn’s Reid Hoffman, the second-biggest Democrat donor of 2024, poured $6 million into the PAC. Billionaire hedge fund manager Seth Klarman gave it another $5 million while gifting millions more to top Democrat PACs.
Sam Rawlings Walton, the liberal grandson of the famously conservative founder of Wal-Mart, contributed $1.3 million. Another $2 million came from John Pritzker. DDT provided the group with an additional $2 million.
Other six-figure contributors include Gordon Gund, former co-owner of multiple sports teams, and Patricia Stryker, co-founder of the Democracy Alliance, a top strategy group for Democrat donors.
“Voting Rights Advocacy”
In October 2021, the PAC — this time calling itself Republicans for Voting Rights — spent $250,000 on billboards that read “TRUMP LOST, NO MORE ‘AUDITS’” across Pennsylvania, Georgia, Arizona, and other states where 2020 election reviews were in motion or under consideration.
An ad on the group’s website contrasts Ronald Reagan as a good Republican against “current Republicans’ efforts to restrict voting[,] undermine democracy[,] and betray America’s deepest values.” One 2020 ad featured a disillusioned Republican voter identifying himself as a “Cheney conservative.” Another portrayed Joe Biden alongside the late Sen. John McCain, saying both men put “country over party” (a phrase Kamala Harris later adopted in 2024).
“The 2020 election was secure and fair. These sham audits are a waste of time and money,” the PAC’s spokeswoman, Amanda Carpenter, told media.
Carpenter simultaneously worked as a writer for the Bulwark from 2020 to 2023, when she left to join the far-left litigation group Protect Democracy, founded by ex-Obama White House counsel Ian Bassin. Protect Democracy is credited for “assembling a bipartisan election-crisis task force” in Time’s infamous February 2021 article, “The Secret History of the Shadow Campaign that Saved the 2020 Election.”
The group’s advisory board includes the Niskanen Center’s Jerry Taylor, failed 2016 presidential candidate Evan McMullin — who was backed by Bulwark mandarin Bill Kristol — and two DDT officials: Mona Charen and Linda Chavez.
Republicans for Voting Rights and DDT (under the name Republicans for the Rule of Law) are listed among 190 “voting rights advocacy organizations” in a January 2022 Yale report on groups trying to pass the Democrats’ Freedom to Vote and John Lewis Voting Rights Acts, both of which would have federalized elections and effectively locked Republicans out of national power.
Other notable members of that “pro-democracy” list: Protect Democracy, David Brock’s Center for Responsibility and Ethics in Washington (CREW), the Arabella-run Center for Secure and Modern Elections, Michelle Obama’s When We All Vote, Greenpeace, Hillary Clinton’s Priorities USA, Stacey Abrams’s Fair Fight, the Lincoln Project, the Democrat get-out-the-vote group State Voices, Ralph Nader’s Public Citizen, People for the American Way, and Rock the Vote.
Besides Kristol, Chavez, and Longwell, Republicans for Voting Rights’ board includes disgraced former RNC chairman Michael Steele, who endorsed both Biden and “Republicans for Kamala,” and liberal ex-Republican Reps. Charles Djou (HI) and Mickey Edwards (OK). Notably, Steele hosts a Bulwark podcast where he has interviewed House Minority Leader Hakeem Jeffries (D), Democratic messaging strategists, and Rick Wilson, among others.
Fear and Loathing in the Swamp
The Republican Accountability PAC maintains close ties with the Niskanen Center. Mickey Edwards, for instance, was a signatory to a 2019 Niskanen Center open letter urging congressional Republicans to oppose Trump’s national emergency, which he used to free up funds for the border wall. Other signatories included Protect Democracy staffer Soren Dayton (now a senior Niskanen director), the Lincoln Project’s Rick Wilson, and three DDT leaders: Bill Kristol, Linda Chavez, and Charlie Sykes.
Both Niskanen and DDT joined a coalition of Never Trump groups to encourage vote-by-mail ahead of the 2020 election. That same year, DDT’s Mona Charen and Amanda Carpenter were key speakers at a Convention on Founding Principles, a joint project of the Niskanen Center and Evan McMullin’s Stand Up Republic that sought to “bring…together principled and former Republican and independent voters in opposition to the renomination of Donald Trump and in support of a new, more unifying vision for the party and country.” Other speakers included McMullin, James Comey, Michael Hayden, and R. Derek Black, an “advocate for antiracism.”
Niskanen staffers are also regular contributors to the Bulwark and vice versa. For instance, Jerry Taylor has waxed about “his conversion from climate change skepticism” on Charlie Sykes’s Bulwark podcast. Damon Linker, a Niskanen senior fellow and liberal journalist, joined Bulwark policy editor Mona Charen’s podcast in 2022 to hail the partisan January 6 congressional committee.
For her part, Charen has been featured many times in Niskanen Center interviews calling “Trump and his movement…a more significant existential threat to American democracy” than the radical Left.
In a 2021 Bulwark article, Laura K. Field — a Niskanen senior fellow “currently working on a book about the New Right” — blasted the Claremont Institute as a “once-distinguished conservative think tank [that’s] plunged into Trumpism, illiberalism, and lying about the election.” In October 2020, Field gushed in the Bulwark that Trump’s coming defeat “will be thanks in no small part to progressives who were willing to compromise, to ‘liberal hysteria’” over his threat to democracy, “to Black Lives Matter organizers, and to the so-called Resistance.”
Gabriel Schoenfeld is both a Niskanen Center senior fellow and a Bulwark contributor who advised Mitt Romney’s 2012 presidential campaign. He has written editorials calling for the West to overthrow Vladimir Putin and save Ukraine and the odd hagiography of Adam Schiff’s “fight to save our democracy” — the latter in The Bulwark.
Brink Lindsey, a self-described Republican who heads Niskanen’s Open Society Project, wrote in 2021 that “the Republican party cannot presently be trusted with power,” so “it falls to Democrats to hold off the threat of authoritarian populism,” even if it means persuading conservative “deplorables” who voted for Trump in 2020.
Linda Chavez, too, is both a DDT board member and a Niskanen Center senior fellow, who briefly served as Reagan’s director of the Office of Public Liaison. Chavez runs DDT’s Becoming American Initiative, which “exists to counter the popular misconceptions about immigrants, both documented and undocumented” by quoting Reagan lines. In reality, the group supports citizenship for illegal aliens beginning with the so-called Dreamers, recipients of Obama’s 2012 Deferred Action for Childhood Arrivals (DACA) program covering the children of non-citizens brought to the U.S. illegally by their parents.
How Never Trumpers Lost the 2024 Election
“We’ve been getting politically realigned out of the Republican Party, [we] Bulwark Republicans, the Red Dog Democrats,” Sarah Longwell told senior Obama advisor Dan Pfeiffer just four days before the 2024 election. She predicted a landslide for Kamala Harris: “They’re not doing this road trip with Liz Cheney if they’re not looking at the numbers and thinking, ‘The biggest pool of gettable voters for us right now are these center-right independent disaffected Republicans.”
Never Trumpers were riding high. In October, pundits speculated that Liz Cheney could end up with a senior position in the future Harris administration. At an October 21 town hall in Pennsylvania — moderated by Sarah Longwell — Cheney urged Republicans to dump Trump over the Dobbs decision that overturned Roe v. Wade. “I have been troubled by the extent to which you have women who — as the vice-president said, in some cases have died — who can’t get medical treatment that they need because providers are worried about criminal liability.”
It’s worth pointing out Cheney’s cynical about-face: She launched her congressional career in 2016 on a strong anti-abortion platform with the endorsement of the Susan B. Anthony List, which gives her an “A” ranking on its pro-life scorecard. Now she says state abortion bans “cannot stand,” but only after left-wing donors like Jeffrey Katzenberg spent millions of dollars trying to rescue her failing reelection campaign in 2022.
Bill Kristol himself was once a member of the board of the Susan B. Anthony List, one of the most influential pro-life organizations in the country. Under his leadership, The Weekly Standard was among the most reliably pro-life publications in the country. But his final advice in the 2024 election, published in The Bulwark on November 3, was this: “Reproductive freedom is a crucial issue, and a winning one, and the Harris campaign would be foolish not to make it a closing one in these last couple of days.”
For her part, Sarah Longwell also advised the Kamala Harris campaign to ignore illegal immigration, crime, and male voters and stick to “abortion rights” in an interview with Politico:
Her advice for Harris: Keep abortion rights center stage. When Longwell asks voters what’s top of mind, they usually say prices, immigration and crime. But once her team brings up reproductive rights, it’s all any of the women in her focus groups can talk about… “The way that Donald Trump is trying to run up the numbers with men, she’s got to do the same thing with women,” Longwell says.
How things have changed. For all their work to elect Kamala Harris, Never Trump Inc. ultimately proved a millstone around the Democratic Party’s neck — and Democrats couldn’t be more bitter.
“Liz Cheney was an electoral fiasco for Kamala Harris,” blasted the Nation a week after Election Day. “The notion that spending day after day with Liz Cheney—who publicly trumpeted an endorsement from her father, former vice president Dick Cheney, and other right-wing Republicans—would benefit Harris turned out to be a damaging distraction for Democrats…Every minute that Kamala Harris spent with Liz Cheney was a colossal waste of the candidate’s time.”
Kamala’s “closing flurry of campaign stops with former Republican Rep. Liz Cheney…may have actively alienated young people and lower-propensity voters who were looking for change,” noted Newsweek. “Nothing says ‘I am the status quo’ more than cavorting with a widely disliked Republican congresswoman who is the icon of a long-vanished Republican political coalition that steered the country into several gigantic icebergs in the early 2000s and which no longer has any meaningful political constituency in America.”
“Pandering to Republicans was one of Harris’s biggest electoral mistakes,” the Alabama Political Reporter opined, noting that Democrat turnout declined even in the conservative state’s most liberal areas.
“The fact is that the mythical ‘Never Trump Republican’ barely exists outside of the media and internet,” one commentator wrote. “But the Democratic Party bet its entire strategy on this political unicorn.”
Not everyone was surprised by the result, however. Again from Newsweek: Harris’s tour with Cheney “is without a doubt one of the most inexplicable stretch-run decisions I’ve ever seen from a major party nominee, and it is a sign of deep, structural delusion inside the Harris campaign and Democratic elites.” That was October 24.
“The Never Trump moment is over,” the far-left New Republic also warned weeks before Election Day. “Does Kamala Harris realize it?”
For their part, glum Bulwark leadership admitted on their Election Day watch party livestream that any opposition to Trump’s second administration will have “no national base of power. It really will be a series of conflicts between state governments and the federal government.”
I’ve charted out the Left’s emerging strategy for building a second Trump “resistance.” So far, it looks very little like the first with its “pussy hats” and mass demonstrations. After burning a billion dollars on Kamala Harris, left-wing donors are tightening wallets and going on the defensive. Some are even blaming Washington’s extensive network of activist organizations for pushing their party too far left. The progressive groups that will succeed in 2025’s cutthroat climate are the ones that show results — particularly in court, where Democrats will focus their efforts to save the administrative state and stymy Elon Musk and Vivek Ramaswamy’s Department of Government Efficiency.
Missing from that list: anyone from Never Trumpland. Attempting to triangulate between the far-left and their former party while playing at “principled” conservatives, Kristol et al. merely alienated themselves from both camps, irreversibly damaging any remaining credibility among Republican voters and Democrat strategists alike. Despite their spending a fortune against him, Trump has emerged stronger than ever and will be termed out after 2028. He crushed the last primary opponent he will ever face — the squish Nikki Haley — united the Republican Party, and deeply eroded the Democrats’ base with working class and non-white voters. Liberal donors will wonder: What’s the point of lining Never Trump’s pockets after 2024?
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