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Breaking Points

What led Trump’s most prominent former supporters to give up on him.
September 14, 2020
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(Hannah Yoest / Shutterstock)

For all the loyalty Donald Trump enjoys from his most sycophantic followers, many prominent figures who famously assisted him have given up on the president altogether. It’s worth taking a look at the breaking points for these various White House staffers, cabinet secretaries, political advisers, and others—the moment when each decided he or she just couldn’t stick with Trump anymore. Because we can learn a lot about Trump and the overall effect he is having on our country by studying what made these individuals—from revered military leaders to Trump’s sleazy surrogates—finally snap.

Of the men and women who have served Trump and gone on to publicly speak against him, perhaps no one’s words carry more weight than Trump’s former defense secretary James Mattis. Theoretically, the “warrior monk” General “Mad Dog” Mattis, a retired four-star Marine Corps general, who once led Central Command, should have been a good fit inside the Trump administration.

But Trump is a reckless force that not even a military general with 40 years experience could counsel. Mattis walked out on Trump in December 2018 when the president ignored his advice and abruptly pulled troops out of the Middle East. Mattis is quoted in Bob Woodward’s new book, Rage, as saying, “When I was basically directed to do something that I thought went beyond stupid to felony stupid, strategically jeopardizing our place in the world and everything else, that’s when I quit.”

That’s not the only deep disagreement he’s had with the president, though. When Trump used military force to disperse protesters in Washington, D.C.’s Lafayette Square, Mattis took the rare step of issuing a public statement on the matter, putting it in no uncertain terms that Trump has crossed an intolerable line.

Mattis said he was “angry and appalled” at the president’s actions, and “We are witnessing the consequences of three years without mature leadership. We can unite without him, drawing on the strengths inherent in our civil society.” He went on, “We know that we are better than the abuse of executive authority that we witnessed in Lafayette Square. We must reject and hold accountable those in office who would make a mockery of our Constitution.” Then he called for the adoption of a “new path” that could only be interpreted as one leading away from Trump.

John Bolton arrived at a similar conclusion after working directly with Trump as his national security advisor. In his book, The Room Where It Happened, Bolton says he decided he had to leave in September 2019, after Trump made plans to invite the Taliban to Camp David public.

Bolton vociferously opposed the idea and hoped word of the plans would never get out. Those hopes evaporated when Trump, without any warning, tweeted about the abandoned project on September 7. On September 9, Trump called Bolton in for a meeting to complain about the press coverage over the canceled meeting and the uproar among Republicans. Trump accused Bolton of leaking, to which Bolton observed dryly, “Of course, most of the negative reaction he had brought on himself by his ill-advised tweets.”

“That was my last conversation with Trump,” Bolton said. On September 10, he delivered his resignation letter at 11:30 a.m. By noon Trump was tweeting that Bolton’s services were no longer needed. “And with that, I was a free man again,” Bolton wrote.

Like Mattis, Bolton is calling for a movement to reject Trump.

“The day after the election, whether Trump wins or loses, we face a real debate, maybe an existential debate, about what the future of the Republican Party is,” he said. He added, “I just think it’s important for the Republican Party to separate itself from Trump and for the conservative philosophy to separate itself from Trump.”


Other insiders, such as Miles Taylor, former chief of staff to Department of Homeland Security Secretary John Kelly, found themselves similarly making great exertions to block other dangerous Trump plans. Like many other appointees, Taylor had misgivings about Trump but accepted a government position thinking he could help prevent Trump from acting on his worst impulses.

“The total tonnage of bad Trump ideas that never materialized were enough to crush anyone’s hopes about a successful presidency,” Taylor told The Bulwark. “But the one that broke my desire to continue serving was his perverse insistence on resuming family separation at the border—and making it worse. It was sick, wrong, and un-American. That’s when it became clear that saying ‘no’ to Trump was no longer enough. His magnetic attraction to wrongdoing outweighed any good the ‘Axis of Adults’ could do to keep him on the right track.”

Elizabeth Neumann, Trump’s former assistant secretary for counterrorism and threat prevention at DHS, recently told Charlie Sykes on The Bulwark podcast that she distinctly remembers when she felt she had to cut loose.

“The point at which my position changed and I said ‘No at this point you are culpable’ was after El Paso,” she said, referring to the August 2019 attack by a white man who killed 20 people and injured dozens more at a Walmart in El Paso, Texas. Echoing Trump’s language, the shooter wrote in a manifesto that “this attack is a response to the Hispanic invasion of Texas.”

“Post-El Paso, there is no excuse,” she said. “The correlation was so clear that this individual carried out this attack because of this language” that Trump had used. She continued, “We see it on full display this summer, it is part of my own process of coming to grips with the fact that I could not vote for him and not just decide to do a write-in candidate but to vote for Joe Biden is realizing how dangerous his rhetoric is and his unwillingness to change. It is so clear to me that his values, what he cares about is himself, he cares about his political power, he cares about winning, and at the sacrifice of people dying. I just cannot.”

Neumann resigned in April 2020 and is now working with Taylor on an anti-Trump group called Republican Political Alliance for Integrity and Reform (REPAIR) to organize others who have worked for Trump and wish to support Biden in 2020 and work together to reform the GOP.


Significant cracks have emerged as well in Trump’s support among individuals outside the administration.

It was Trump’s callousness toward others that moved Stephanie Ranade Krider, executive director for Ohio Right to Life, to quit her job rather than endorse Trump and help him win a second term. “You learn to hold certain things in tension, and for me, it came to a point where I couldn’t anymore,” Krider recently told Christianity Today.

“Always, there has been this undercurrent where he just does not respect women and he does not like black and brown people. I can’t look at any of his behavior and see evidence of the Holy Spirit in his life. Nothing about his words or actions are kind or gentle or faithful or full of self-control.” Krider specifically mentioned Trump’s child separation policy and his handling of the killing of George Floyd as reasons for her break. “My greatest fear is that in the pro-life movement and the evangelical church, we’ve become so tied to the Republican Party and President Trump, they don’t all matter to us,” she said.

Other committed Republicans have found Trump’s attitude towards the elections appalling.

Steven G. Calabresi, cofounder of the Federalist Society and a professor at Northwestern University’s Pritzker School of Law who supported Trump through impeachment, said in July that Trump’s tweets raising the possibility of postponing the election were causes for removal.

“I have voted Republican in every presidential election since 1980, including voting for Donald Trump in 2016. I wrote op-eds and a law review article protesting what I believe was an unconstitutional investigation by Robert Mueller. I also wrote an op-ed opposing President Trump’s impeachment,” Calabresi wrote. “But I am frankly appalled by the president’s recent tweet seeking to postpone the November election. Until recently, I had taken as political hyperbole the Democrats’ assertion that President Trump is a fascist. But this latest tweet is fascistic and is itself grounds for the president’s immediate impeachment again by the House of Representatives and his removal from office by the Senate.”


While it’s one thing for experts to quietly acknowledge Trump’s flaws and put that aside in a faithful attempt to preserve institutional guardrails and pursue policy goals, those who professed there was something redeeming about his personal character don’t have the same credibility. Regardless, the stories they tell to explain their U-turns show that Trump’s slavish followers are capable of walking away. Even the most shameless opportunists can usually tell when their opportunity has run out.

Take, for example, Anthony Scaramucci, who professed his “love“ for Trump in his only press conference during his 11-day stint as White House communications director, and has now remade himself an anti-Trump crusader. He attributes his turnaround to Trump’s racialized attacks on opponents.

Similar reasoning was voiced by Omarosa Manigault Newman, a Trump hanger-on from the first season of The Apprentice who only stuck around on the White House staff for the first season of his presidency. Omarosa once described Trump as “the right choice for America“ and said “every critic, every detractor will have to bow down to President Trump.” But in her 2018 memoir of her time in the White House, Unhinged, she describes how she came to realize Trump is “a racist, a bigot, and a misogynist” whose actions were “harming the country,” and that she “could no longer be a part of this madness.” When she was fired by chief of staff John Kelly, she said she felt relief: “For the first time in nearly fifteen years, I would be free from the cult of Trumpworld.”

Other backers say Trump simply let them down.

Back in 2016, right-wing provocateur Ann Coulter wrote a book extolling Trump’s virtues. By this year, she’d had enough; she called Trump “the most disloyal actual retard that has ever set foot in the Oval Office.” She’s mostly upset that Trump didn’t deliver on his vows to build the border wall and stop illegal immigration. “I will never apologize for supporting the issues that candidate Trump advocated, but I am deeply sorry for thinking that this shallow and broken man would show even some remote fealty to the promises that got him elected,” she tweeted.


The concept of one-way loyalty is a common theme among those who have abandoned their support for Trump. The closer one gets to Trump, the more that feeling seems to intensify when they eventually realize their fidelity is unrequited.

In his new book, Disloyal, longtime Trump fixer Michael Cohen lays out all the various unethical and criminal schemes he participated in service to Trump. Like Coulter, he didn’t wrap his head around breaking with Trump until it was abundantly clear how cravenly he had been used.

Cohen recounts feeling betrayed by Trump when it looked as if he would not be repaid the hush money he paid out of his pocket to conceal Trump’s alleged affairs during the election. Cohen expected a hefty Christmas bonus to recover the funds and when he didn’t get it in his 2016 Christmas card he said he was “surprised,” dismayed,” “astounded,” and “outraged” just to name a handful of the words he used to describe his reaction.

“Something in me was broken by this disrespect and presumption at the whim of now President-Elect Trump,” he wrote. “My payment, and all the hellfire and damnation that ensued, up to and including my circumstances as inmate number 86067-054 in Otisville federal prison, stemmed from that ingratitude and dishonesty.”

Still, Cohen didn’t openly turn against Trump until after FBI agents raided Cohen’s apartment in April 2018. Cohen wrote that he found himself thinking, “I was now on the other side of the power dynamic I had exploited so often on behalf of Donald Trump.” Trump promised Cohen in a phone call, “I have your back. You’re going to be fine.” Cohen wrote, “That was Trump’s mantra and exhortation: the President had my back. If I stayed loyal to Trump, he would stay loyal to me. I had to stay the course. Always stay the course. Be loyal. I was going to be fine.” But that wasn’t true.

Cohen was later sentenced to three years in jail. And Cohen never spoke to Trump again.

First Lady Melania Trump’s former friend and confidante Stephanie Winston Wolkoff also recounts the anger and humiliation she felt after being hung out to dry by the Trumps.

Wolkoff, a close friend of Melania’s who had previously organized major events, including New York’s famed Met Gala, agreed to produce Trump’s inauguration events. But then the press started looking into spending irregularities around her productions. Wolkoff believes she was unfairly set up to take the blame due to her lack of experience in the political world.

“Melania and the White House had accused me of criminal activity and publicly shamed and fired me and made me their scapegoat,” Wolkoff told MSNBC’s Rachel Maddow. “At that moment in time, that’s when I pressed record. She was no longer my friend and she was willing to let them take me down.”

As she writes in her tell-all, Melania and Me, “It was the worst mistake of my life to get involved with Melania and the Trumps: emotionally, mentally, physically, financially, socially, professionally.”

“In fact, I wish I had never met her,” Wolkoff wrote.


These tales are easily lost in the deluge of news pouring out of the Trump Administration. Such complaints are routinely dismissed by Trump’s latest surrogates as sour grapes from disgruntled former employees. Trump taps out tweets disparaging the character of these former loyalists and, just like that, their names melt into the social media white noise of the Trump era.

Except when you take a step back, a few common chords ring through and rise above the petty back and forth. We should pay attention because it matters far more than Trump’s personal relationships with these people.

The people most willing to assist Trump tell us he is a person with disastrous foreign policy ideas. They say he shows disrespect for the Constitution and displays a lack of empathy or concern for the humanity of others. He threatens our democratic process. He expects his allies to accept blame for his misdeeds.

The characters are different, but all their stories are the same. Trump pushes people to take unethical, dangerous, and even criminal actions for his benefit.

That’s just who Trump is. He tries to corrupt those around him. This is why—in addition to the desire to sell books—so many people have been coming out in recent weeks to explain their disenchantment with Trump. They know that if he gets a second term, he will keep corrupting America, too.

Amanda Carpenter

Bulwark political columnist Amanda Carpenter is a CNN contributor, author, and former communications director to Sen. Ted Cruz and speechwriter to Sen. Jim DeMint.