While Kristol would be a new name to many on the Left during the Trump era, he already is well known on the Right. A conservative thought leader and quarterback for the Iraq War, Kristol long had occupied a premium spot in the Republican Party’s hierarchy. After Bill Clinton beat his boss in 1992, Kristol helped lead the Republican Party out of the political wilderness at a time when many predicted the GOP was finished.
A series of memos, authored by Kristol, detailed a strategy to defeat Hillary Clinton’s universal health care legislation.2 Clinton’s plan went down in flames in late 1993 before a bill even made it to the floor of the Democratically controlled US Senate. The following year, in large part due to the demise of the Clinton health care proposal and fear it could be resurrected, fired-up Republican voters elected a Republican-majority House of Representatives for the first time in 50 years.
Kristol’s memos morphed into the Weekly Standard, a thin but influential magazine that debuted in 1995. It featured several top-notch conservative writers; the publication was a must-read in the Bush White House and served as a crucial organ of pro–Iraq War propaganda before, during, and after the deadly conflict. The animating ideas of neoconservatism, a political philosophy conceived by Kristol’s father, Irving, played out in the pages of the Standard.
Kristol was a regular on Sunday news shows and even earned a spot in the New York Times editorial pages. He was a Beltway-accepted promoter of conservative thought and Republican Party politics.
But when Trump won the Republican nomination for president against his wishes, Kristol turned on the insubordinate party that had powered his gravy train for decades. He became the self-appointed leader of what evolved into “NeverTrump,” a small assortment of embittered, parochial “conservatives” enraged over Trump’s candidacy. Consumed with their self-importance and alarmed at their potential demotion within the GOP, they pledged to crush the brash interloper who had never edited a very important magazine or toiled at a very important conservative foundation.
Acting as a political Praetorian Guard of sorts, this group behaved as though they, not elected officials or—ew, gross—Republican voters, called the shots. NeverTrump leveraged their long-cultivated Rolodex of powerful press contacts to hit cable news shows and Twitter to express their displeasure about Trump’s candidacy.
Interestingly, the early battle between Team Trump and Team Kristol would be a proxy between the old guard and a national GOP agitated at its gutless party leadership; party faithful saw little daylight between Beltway Republicans and Democrats. A Queens-born international businessman who in no small measure owes his success to his father versus a Manhattan-born political guru who in no small measure also owes his success to his father—not exactly the head-to-head challenge that loyal Republicans asked for in 2016. But there we were.
“To Trump, Kristol is the rigged system he’s fighting against, the personification of an elite establishment overdue for a rude awakening,” noted Michael Crowley in a July 2016 profile on Kristol. “And, of course, Trump’s not entirely wrong about that.”3
Kristol started trolling Trump shortly after he launched his campaign from the luxury hotel in New York City that bears his name. Throughout the last half of 2015, Kristol predicted Trump’s campaign would end before the ball dropped in Times Square; he even started a Twitter hashtag—#PeakTrump—to assure his followers that The Donald’s days were numbered.4 (It was a warning he would give repeatedly throughout the Republican primaries, general election, and Trump’s first term as president.) “From the beginning of the billionaire’s campaign, there has been no better contra-indicator of whether a given controversy would affect Trump than Bill Kristol’s Twitter feed,” one writer for New York magazine presciently noted in January 2016.5
That same month, Kristol joined like-minded conservatives in what will forever be considered the establishment’s declaration of war against Donald Trump and his supporters.
BUCKLEY’S BRETHREN TAKE AIM AT TRUMP
On the eve of the 2016 Republican primary season, nearly two dozen conservative influencers took to the pages of National Review, the conservative movement’s most esteemed magazine, to contribute to the publication’s infamous “Against Trump” issue.6 Every page was devoted to discrediting the rogue candidate at the time leading an impressive field of Republican governors, senators, and business executives.
Known for its mantra, “standing athwart history, yelling Stop,” the publication founded by William F. Buckley Jr. in the 1950s attempted to stand athwart the accelerating freight train of Donald Trump’s presidential candidacy and yell to his supporters, “’Don’t you dare.”
Contributors included Kristol, broadcaster Glenn Beck, columnist Cal Thomas, scholar Thomas Sowell, and a handful of George W. Bush administration officials. It was a collection of some of the most powerful and revered names in the conservative movement at the time.
“Donald Trump is a menace to American conservatism who would take the work of generations and trample it underfoot in behalf of a populism as heedless and crude as the Donald himself,” wrote editor-in-chief Rich Lowry and his colleagues. And that was kind compared to the other rants featured in the issue.
In fairness, National Review editors and contributors had reason to suspect Donald Trump was not one of “them.” A brash billionaire with political pals on both sides of the aisle and no record of fealty to conservative principles—“gaping holes” in his record, the NR editors truthfully surmised—Trump deserved legitimate scrutiny by Republican Party stalwarts. Bill and Hillary Clinton, after all, had attended Trump’s wedding to Melania.
Trump’s views on foreign affairs and social policies important to conservatives over time were erratic if not alarming. Pro-life conservatives were justifiably concerned after he suggested in 2015 that it was “possible” he once donated to Planned Parenthood.7 Further, his stance on gun control was unclear, as he once called out NRA-funded Republicans and boosted a ban on so-called “assault rifles.”8
But the “Against Trump” issue came across as a vanity project that smacked of both desperation and arrogance. Commentary veered from sober analysis to self-serving moralizing. Some contributors regurgitated the Democrats’ most inflammatory charges against Trump, including accusations he was a racist, a sexist, and an Islamophobe—pure irony from thought leaders of a political party accused of the same wickedness by the Left for decades.
“Trump has made a career out of egotism, while conservatism implies a certain modesty about government. The two cannot mix,” warned longtime conservative commentator Mona Charen, unwittingly making the pro-Trump case for conservatives who think the two are not only compatible but essential.
“Should his election results match his polls, he would be, unquestionably, the worst thing to happen to the American common culture in my lifetime,” complained John Podhoretz, editor of Commentary magazine, the publication run for more than 30 years by his father Norman Podhoretz, the distinguished (and pro-Trump) public intellectual.
They—accurately—interpreted Trump’s support as a bootheel kick to the collective groin of the weak, eager-to-please, and largely incompetent conservative ruling class. “If Trump were to become the president, the Republican nominee, or even a failed candidate with strong conservative support, what would that say about conservatives?” asked National Review editor Rich Lowry and his colleagues.9
In the succeeding 10 months, Lowry would get his answer. And it would require not more condemnation of Trump and his conservative backers but a long look in the mirror.
Concern over Trump’s shaky conservative street cred wasn’t their only beef: Trump’s demeanor, mannerisms, and thrice-married status offended the Brahmin sensibilities of the National Review class. “Can conservatives really believe that, if elected, Trump would care about protecting the family’s place in society when his own life is—unapologetically—what conservatives used to recognize as decadent?” asked Russell Moore. “It is not just that he has abandoned one wife after another for a