They remain a mere slice of the conservative world, elites in common cause with Democrats, in the tradition of “the enemy of my enemy is my friend.” But as the November midterms approach, Trump critics within the GOP orbit are raising their voices, drawing battle lines, and getting organized – if only along the edges. Neoconservative commentator Bill Kristol has launched a multipronged initiative, Defending Democracy Together , to defend free trade, immigration, and special counsel Robert Mueller’s investigation into the Trump campaign and Russia. Another project, Republicans Against Putin, is in the works. The goal isn’t necessarily to win over a majority of the party, but to promote their positions on issues and to encourage Republicans in Congress who are privately unhappy with the president to go public. For many conservative Trump critics, it’s been both a difficult and liberating time. “I used to be part of the Republican cocoon, and I have completely broken from that,” says columnist Max Boot. “I left my tribe behind, and am now politically homeless, and forced to really think for myself in a way that partisans often don’t do.”

Max Boot’s life changed the moment Donald Trump announced for president.

Suddenly, the lifelong conservative Republican – historian, author, foreign-policy adviser to three GOP presidential candidates – began to question his place in his adopted home. Mr. Boot, who is Jewish, had fled the Soviet Union as a boy with his family, and here was a major Republican contender tarring immigrants in the ugliest of terms.

“I was outraged when he came down the escalator at Trump Tower, denouncing Mexicans as rapists and drug dealers, and my outrage has not diminished at all since,” says Boot, now a columnist at The Washington Post, in an interview. “Writing is my therapy.”

Boot quit the Republican Party, and now decries President Trump regularly on cable TV alongside Democrats and other elite “Never Trumpers,” some still inside the GOP tent, others in the political wilderness like Boot. The term “strange bedfellows” almost no longer applies; at this point, these one-time ideological adversaries have the on-screen rapport of old friends.

“It’s a very odd place to be in,” says Florida-based GOP consultant Rick Wilson, another vocal Trump critic and cable TV regular.

As the November midterms approach, Trump critics within the GOP orbit are raising their voices, drawing battle lines, and getting organized, if only along the edges. Many speak of their fight in moral terms. They remain a mere slice of the conservative world, elites in common cause with Democrats, in the tradition of “the enemy of my enemy is my friend.”

But the famous names attached to Never Trump-ism give their message outsize reach. Some, like columnist George Will, strategists Steve Schmidt and Mary Matalin, and TV host Joe Scarborough, have quit the Republican Party. Some too, like Boot, openly hope the Democrats retake the House, as a check on Trump and Trump-ism.

Others remain Republican, choosing to fight Trump from within, on a case-by-case basis – still applauding the president at times. Trump’s two Supreme Court picks have received high marks among conservatives, including Never Trumpers.

This week, billionaire Charles Koch and his political network entered the mix – not as Never Trumpers, but megadonor Republicans willing to speak out against Trump policies. Mr. Koch, who didn’t back Trump in 2016, warned about protectionism Sunday at his network’s annual summit, and said he will fund or not fund candidates based on where they stand on issues, not party affiliation. Trump’s response – tweeting Tuesday that the “globalist” Koch brothers “are against Strong Borders and Powerful Trade” – only reinforced the president’s willingness to further yank the party that elected him away from some of its core principles.

It’s possible, some observers say, that the image of bipartisan elites, fighting Trump arm-in-arm, could actually help him.

“They reinforce that he’s an anti-establishment figure,” says Democratic pollster Mark Penn.

For now, some top Never Trumpers are focused on organizing. In April, neoconservative commentator and Weekly Standard founder Bill Kristol launched a multi-pronged initiative, Defending Democracy Together, to defend free trade, immigration, and special counsel Robert Mueller’s investigation into the Trump campaign and Russia. Another project, Republicans Against Putin, targeting the Russian president, is in the works.

But do any of these efforts – Mr. Kristol’s, all the cable TV shouting, the ads, the books Never Trumpers are writing, the open letters – have an impact?

Among his base, Trump is Teflon Don. In fact, since December, his overall job approval has risen from an average 37 percent support to 43 percent – with support among Republicans solidly above 80 percent. True, the number of Americans who identify as Republican has declined slightly since Trump took office, but his base of support – which includes non-Republicans captivated by Trump’s populist message – remains a significant force, says polling expert Charles Franklin.

Even when Republican-leaning independents are included among polled Republicans, Trump’s support is high, “and the group isn’t shrinking that dramatically,” says Mr. Franklin, director of the Marquette Law School Poll in Milwaukee.

Ask GOP Trump critics if their anguished writings and televised primal screams are having the desired impact, and they pause.

“Good question,” says Republican consultant Rick Tyler, who rejects the label “Never Trumper” but is often seen nodding alongside liberal Democrats as a political analyst on MSNBC.

“Look at it this way: He should be in the 60s,” Mr. Tyler adds, referring to Trump’s job approval. “We have 4.1 percent economic growth, historically low unemployment across every demographic, and the stock market is doing rather well. At minimum he should be at 50 [percent].”

And, other Trump critics note, the goal isn’t necessarily to win over a majority of the party, but rather just enough to encourage Republicans in Congress who are privately unhappy with the president on key policies to go public and take action. Projects like Kristol’s aim to articulate the conservative principles his group says Trump is flouting.

Ads by Kristol’s group have appeared on Fox News – a rare opportunity for the Never Trump message to reach a conservative audience. Kristol, Boot, Tyler, and others in the Never Trump stable are regulars only on the left-leaning MSNBC or CNN.

Sarah Longwell, a GOP strategist working with Kristol on the Defending Democracy Together initiatives, says the goal is both to provide cover for congressional Republicans and generate enthusiasm for their positions on the targeted issues – trade, immigration, the Mueller investigation, and President Vladimir Putin.

“Everyone seems to have forgotten how much power Congress actually has, for example on tariffs,” says Ms. Longwell. “We’re trying, as a group, to say, ‘We’re all Republicans, let’s serve as a check in areas where the president is moving against everything the Republican Party has stood for.’ ”

Friendships and jobs lost

Being a Never Trumper can be emotionally draining. Some have lost friendships and paid work. Tyler recently lost his gig as a communications adviser to Mississippi Senate candidate Chris McDaniel (R) when the two parted ways over their divergent views of Trump.

Tyler also lost a friendship with a Republican he describes as a well-paid political consultant.

“He used to care which team and which kinds of candidates he worked for, but now is willing to work for anybody, because it pays the bills,” says Tyler. “He calls me a sellout, because I make money going on MSNBC and criticizing Trump. But I’d still go on MSNBC and criticize Trump even if they weren’t paying me.”

Tyler says he argues with his dad, a solid Trump supporter, all the time.

“I’m like, ‘Dad, what’s Trump’s strategy on trade?’ Tyler says. To which his dad replies, “He knows what he’s doing, and he has a strategy, and you’ll see.” Tyler’s response: “That’s not good enough. Sorry.”

In spite of it all, Tyler says his relationship with his dad is great. “He calls me a liberal, and occasionally yells at me,” Tyler says. “But he’s never ended a conversation without saying, ‘I love you and I’m very proud of you.’ ”

Wilson, the GOP consultant in Florida, has also faced blowback from fellow Republicans, but mostly over his work opposing former Judge Roy Moore (R) in the special Senate race last December. Mr. Moore was endorsed by Trump, but still lost to the Democrat, a stunning upset in deep-red Alabama that shaved the Republican Senate majority to just two seats.

“I saw a moral imperative absolutely to put party aside, because of who that man was and what he had done,” says Mr. Wilson, referring to allegations that Moore had sexually assaulted women and underage girls.

For Wilson, the race raised existential questions about the Republican Party. “Can the party back [a man like Moore] and keep its soul?” he says. “I was pretty sure the answer was no.”

Now Wilson is focused on his forthcoming book, “Everything Trump Touches Dies.” But despite the downer of a title, Wilson is ever the happy warrior.

“I wake up every day, and I love it,” he says, calling himself a “Republican apostate” in a party that has sold itself to Trump.

“I have these nonsensical beliefs in free markets, personal liberty, the Constitution, all those things that I was told for many years the party stood for,” Wilson says. “Now apparently we stand for trade wars, grabbing [women], and crazy-tweeting ourselves to the brink of nuclear war.”

Wilson also calls himself a “Father Confessor,” fielding calls nearly every day from Republican elected officials who are completely miserable having to defend Trump.

On Capitol Hill, only a few Republicans in Congress battle Trump openly – and all are on their way out, senators like John McCain, Jeff Flake, and Bob Corker, along with House members who are either retiring or, as in the case of Mark Sanford, lost the primary after defying Trump in public.

“I’m fortunate that my livelihood does not depend on political affiliation,” says Jack Pitney, a political science professor at Claremont McKenna College in Claremont, Calif.

Professor Pitney, a former Republican Hill staffer, quotes Ronald Reagan when he’s asked why he quit the GOP: “My party left me.” He also mentions Trump’s character. When Trump went after Pitney’s former student, Heidi Cruz – Texas Sen. Ted Cruz’s wife – “I took that personally,” Pitney says.

Life outside the GOP cocoon

Books attacking and defending Trump are now all the rage – with Trump allies like Jeanine Pirro, Alan Dershowitz, Gregg Jarrett, and Newt Gingrich releasing tomes at least as fast as the Trump critics.

Among the prominent female Never Trumpers, Amanda Carpenter recently released “Gaslighting America: Why We Love it When Trump Lies to Us,” a deconstruction of Trump’s communication style. Ms. Carpenter, like Tyler, was a top aide to Senator Cruz and is now a CNN commentator.

Boot’s latest book – “The Corrosion of Conservatism: Why I Left the Right,” due out in October – promises to be part memoir, part commentary on this extraordinary political era.

“I used to be part of the Republican cocoon, and I have completely broken from that,” says Boot, who began his career as a reporter and editor at the Monitor. “I left my tribe behind, and am now politically homeless, and forced to really think for myself in a way that partisans often don’t do.”

Still, Boot seems to have found a new tribe – elites and intellectuals who have rejected Trump. He mentions a new group called Patriots and Pragmatists, described by The New York Times as a coalition of “leading donors and operatives from the right and left.” He has also signed on to another nonpartisan effort called the Renew Democracy Initiative, which is releasing a book of essays in October.

The goal of these efforts joining the center-right and center-left, Boot says, is to oppose the “populist threat represented not just by Trump but also [Marine] LePen in France and many other rabble-rousers in the Western world.”

Boot says he voted for Hillary Clinton in 2016, and would even consider becoming a Democrat if the party went in a centrist direction. But with the Democrats heading leftward, Boot looks set to remain politically homeless for now.

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Most conservative Trump critics don’t even consider jumping to the other major party.

“I love Democrats,” says Tyler. “I just don’t want them to be in charge of anything.”