Donald Trump, Dan Quayle, Sarah Palin, Alan Keyes and Clarence Thomas all have one thing in common—William Kristol has spoken up for all of them when others—even conservatives—have been skeptical. There's always been a good deal of Dr. Frankenstein in Kristol's make-up, so it's no surprise when he helps create the GOP's worst experiments-gone-awry. Trump's racist attacks against Judge Gonzalo Curiel have suddenly made Kristol's current anti-Trump position seem sober compared to the likes of die-hard party men like Paul Ryan, whose endorsement timing could not have been worse. But when Trump first announced, and drew fire from some for his blatant anti-Latino racism, Kristol quickly came to Trump's defense:

"I'm not a Trump fan, I don't think he should be the Republican nominee, but it's ridiculous," Kristol said Tuesday on "The Steve Malzberg Show."

"It's very, very foolish if the Republican establishment or the Republican candidates treat him with disdain instead of saying, you know what, good to have more voices, good to have some unconventional voices in the race."

This was hardly out of character. Over the past three decades, Kristol's done a great deal to facilitate the rise of Donald Trump, particularly when it comes to promoting figures of dubious distinction, with murky policy positions. Kristol's crackpot crusades have helped fissure the party, while fueling the notion that unconventional figures who irritate liberals are an ideal type for conservative leadership. Trump is simply the next logical step in the progression, the one who's finally taken things so far that even Kristol sees the flaw in the logic—but that might be because he had no direct role in elevating Trump to the fore.

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Sarah Palin is the most obvious figure to compare with Trump, and Kristol's role in getting Sarah Palin the VP nomination in 2008 is the stuff of legend. In June 2007, Kristol and fellow Weekly Standard editor Fred Barnes lunched with Palin in Juneau, when a cruise the magazine hosted set anchor there. After that:

Kristol can fairly lay claim to having “discovered” Palin for Washington political circles. Palin’s name appeared in 41 Weekly Standard articles since the Juneau meeting—starting with a paean entitled “The Most Popular Governor” that ran right after the reception.

Kristol didn't write that story, Barnes did. But that hardly mattered. As Jane Mayer explained in the election's closing days:

The most ardent promoter, however, was Kristol, and his enthusiasm became the talk of Alaska’s political circles.... [A]s early as June 29th, two months before McCain chose her, Kristol predicted on “Fox News Sunday” that “McCain’s going to put Sarah Palin, the governor of Alaska, on the ticket.” He described her as “fantastic,” saying that she could go one-on-one against Obama in basketball, and possibly siphon off Hillary Clinton’s supporters.... On July 22nd, again on Fox, Kristol referred to Palin as “my heartthrob.” He declared, “I don’t know if I can make it through the next three months without her on the ticket.”

Kristol wasn't just a public promoter, he played a key behind-the-scenes role as well, and stayed loyal to Palin long after others had abandoned her. As late as August 2013, Kristol still said that Palin could "resurrect herself" by running for Senate.

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Kristol was hardly alone in seeing what he wanted to see in Sarah Palin. He was, if anything, her biggest mark. Dan Quayle had no such record of deceiving folks left and right. Yet Kristol saw great potential in Quayle as well, quickly rising to become his chief of staff, and become known as “Quayle's Brain.” As the New Republic reported:

Kristol's basic strategy is to carve out a number of niches for Quayle to occupy. He wants the vice president to handle a few selected issues quietly and well, without taking unnecessary risks. And so far that's exactly what Quayle has tried to do. As head of the Space Council, he has played a key role in winning the president's backing for a manned mission to Mars, and for the space program in general.

Why yes! We all remember the Bush/Quayle Mars Mission, don't we? Don't we? It's really amazing that we don't, considering what a crafty plan Kristol had in mind for making Dan Quayle great:

Kristol thinks that word of Quayle's competence is bound to spread once it has solidified within the White House. “The key thing in the first year was to establish himself as an important player within the administration and on the Hill,” says Kristol. “The second-level audience it was important to pay a lot of attention to was the Republican Party. The third circle is the public. If you had people in the West Wing today who were saying Dan Quayle's not a player, he's not involved, he's not influential, all the greatest p.r. in the world wouldn't work because it would be totally undercut.”

It all sounds perfectly reasonable, a logical, straight-forward progression, if you forget that the man it's all centered on is Dan Quayle. And that's the sort of thing that only Bill Kristol seems able to forget, over and over and over again. The account continued:

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It's a nice theory, but can Quayle really do anything about his pathetic twenty-nine percent public approval rating? “The fact that we have not made huge progress on the public image front yet is neither a surprise nor particularly disturbing,” Kristol says. He thinks the vice president's image will gain this year, as Quayle improves his television skills with coaching from Roger Ailes and travels around the country to campaign for Republican candidates.

Twenty years later, Sarah Palin would put a lot of energy and passion into convincing people that she had what it takes, and those coaching her were only getting in the way. But with Quayle, the illusion seems to have been generated almost entire by Kristol himself.

Of course, there is one thing that Dan Quayle is remembered for, and it's not the Bush/Quayle Mars Mission. It's Dan Quayle's fight with the equally fictional Murphy Brown, which served to completely distract media attention from any serious reflection on the underlying causes behind the Rodney King uprising. As an act of political misdirection it was nothing short of masterful—though of course that's not how the political elite remembers it. Still, it did seem to signify something serious about Quayle. And yet, it was not a master-stroke of Kristol's planning, much less of any unsuspected innate capacity hidden beneath Quayle's oblivious surface, as a contemporary account explained: Kristol's input has included Quayle's foray into cultural issues, which Kristol knows “many politicians are wary to talk about.” There have been those statements on family values and elitism, including invocation of a famous prime-time name, “Murphy Brown.” Kristol admits that he has still never watched the show and, as far as he knows, Quayle still hasn't. As to who originated the “Murphy Brown” idea, the Quayle camp is unclear. It just sort of came up during discussion for what Kristol believes was “a rather conventional speech” on society's “poverty of values.” The initial newspaper coverage of the San Francisco speech gave passing mention to the TV reference. But the TV networks went wild. “TV drove the story. It seemed like the networks had a personal stake in it,” Kristol said. “She (Murphy Brown) was like them.”

In short, it was the very villain that Quayle was attacking—like Palin and Trump after him—that made his attack famous and gave it all the power it possessed. Neither Kristol nor Quayle had any special savvy or insight, so it's not the least bit surprising that nether has concocted anything similar in the decades since.

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It was not Kristol's first quixotic adventure, though. In the 1988 election he didn't work for Bush/Quayle. Instead, he was campaign manger for Alan Keyes, in his first of many landslide loses, this time against Maryland Senator Paul Sarbanes. Kristol and Keyes had been grad school roommates, so perhaps it shouldn't surprise us that Kristol has repeatedly shown an affinity for oddball would-be political leaders. Keyes was the forerunner for both Herman Cain and Ben Carson, so that by promoting him in 1988, Kristol was in the vanguard of a dynamic that would take decades to gain a wider following. That was his special gift. That same account quotes Kristol on the Keyes campaign:

“I didn't do a real good job, but it was probably hopeless anyway. Still, I'm glad I did it. I learned a lot about politics.”

But not a lot about winning, though. Much less about candidate selection. Details, details....

Keyes is hardly the only interesting special friend worth noting here. While serving as chief of staff to Reagan's Secretary of Education, William Bennett, Kristol forged an enduring friendship with Education Undersecretary Gary Bauer, who later became a leading (though sometimes unorthodox) figure of the religious right. As Corey Robin described, one noted tidbit from Jane Mayer's Strange Justice: The Selling of Clarence Thomas was that:

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Gary Bauer and Bill Kristol vacationed together at the beach each summer, along with their families. In the summer of 1991, at the Delaware shore, they planned the Christian right’s campaign to get Thomas confirmed to the Supreme Court.

This is arguably what Kristol does best, since there were no pesky voters involved, only elite politicians and their biased preconceptions of what those voters would think. And that's the realm in which Kristol excels, as seen in the prime example of Sarah Palin. But Bauer is fascinating in his own right, not least because he showed early policy affinities with the more emergence of Trump—although from much different starting point. In 1998, Mother Jones wrote about Bauer's growing fissure with GOP elites and potential flirtation with Democrats (think former Pennsylvania Governor Bob Casey):

Bauer is leading his flock toward a moralist economic philosophy that often seems more Democratic than Republican.... [Ralph] Reed viewed the religious right as an interest group concerned with a few issues such as abortion and school prayer. Bauer wants to broaden the agenda. "The business wing of the party wants social conservatives to vote Republican, but doesn't like the idea that social conservatives might have ideas about foreign policy or tax policy," says Bill Kristol, the publisher of the Weekly Standard and a friend of Bauer's. "Ralph was willing to abide by that bargain. Gary isn't." Bauer's economic adviser, Jeff Bell, agrees. "Gary is testing the hypothesis that the pro-family movement is ready to break out. It's ready to have an economics and a foreign policy of its own."

Those policies had a lot in common with Trump's today, but came from a much more authentic place:

That economic and foreign policy is class-conscious and populist, thanks in part to Bauer's background. He grew up among Democrats in the blue-collar town of Newport, Kentucky, and was the only member of his extended family to attend college. He speaks of the night his father, an unskilled laborer, cried over the kitchen table after losing his job.

Bauer never managed to get very far with his agenda. Two years later, George W. Bush's phony “compassionate conservative” shtick won over a huge part of the religious right constituency Bauer had hoped to represent. But the logic of his position did not go away, and with Trump, we arguably see the return of the repressed, in typically grotesque form. At least part of Kristol's deep hostility to Trump comes out of profound ambivalence: If Bauer had been more successful, Kristol might have teamed up with him, despite his strong neocon ties, and Bauer's vision was a lot more popular with voters than anyone seemed to realize at the time.

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But there's another source of profound ambivalence underlying Kristol's fraught relationship to Trump, which the New Republic's Jeet Heer explored at length late last August. Heer noted how Kristol's initial defense of Trump had turned to vehement opposition after Trump's dismissal of John McCain as a war hero, only to somewhat turn around again. In his peak anti-Trump phase, Heer noted:

Kristol then went through a phase of constantly and incorrectly predicting Trump’s imminent demise, saying on nine separate occasions that we had hit “peak Trump.”

That only lasted so long, however:

But now that it's clear he was wrong about Trump's staying power, Kristol is articulating an “anti-anti-Trump position.” As Kristol explained in a series of tweets on August 20, “I remain not pro-Trump, but I'm once again drifting into the anti-anti-Trump camp.” Kristol’s feelings about Trump have been going up and down like a yo-yo. How do we explain that?

Heer's explanation was to turn to family history, specifically to Kristol's highly influential father, who in 1952 “published an inflammatory article in Commentary magazine which offered an ambiguous account of the anti-Communist crusader Joseph McCarthy.” Specifically, Heer pointed out:

While the elder Kristol acknowledged that McCarthy was a demagogue, he also thought that liberal critics of the red-baiting senator were worse. In outlining his anti-anti-McCarthy position, Irving Kristol wrote, “For there is one thing that the American people know about Senator McCarthy: He, like them, is unequivocally anti-Communist. About the spokesman for American liberalism, they feel they know no such thing.”

It was, Heer notes, “hugely polarizing.... In philosophic terms, Kristol, in the manner of the political theorist Carl Schmitt, was setting up a basic friend-enemy distinction, allying himself (and the American people) with McCarthy against cosmopolitan liberals, seen as inherently untrustworthy.” If that sounds familiar, it's for good reason, as Heer goes on to note:

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In a 2003 editorial for The Weekly Standard, William Kristol echoed his father’s words to defend Bush’s foreign policy: “But the American people, whatever their doubts about aspects of Bush's foreign policy, know that Bush is serious about fighting terrorists and terrorist states that mean America harm. About Bush's Democratic critics, they know no such thing.”

And—lo and behold!—the exact same “stinking thinking” logic showed up again:

...echoed in William Kristol’s recent anti-ant-Trump tweets: “So much of the sniping at him misses the point. Much of the criticism of Trump has the feel of falling (fairly or unfairly) into the hobgoblin-of-small-minds category. Trump's appeal is that he seems to speak unhesitatingly for America and against our enemies, rivals and threats to our well-being.”

There was a deeper reason for Kristol to echo his father's argument, Heer noted: fear. The elder Kristol and other Jewish intellectuals were driven in part by the fear of being smeared as pro-Communist, simply because they were Jewish. “So Kristol’s anti-anti-McCarthy stance sprang from not just a shared anti-Communism with McCarthy but also the fear that the McCarthyite mob might turn against himself personally, as someone who was Jewish.” A similar fear could well be read into the younger Kristol's ambivalence around that time:

In 1952, Irving Kristol wanted to make sure the McCarthyite mob didn’t go after him. In 2015, William Kristol is trying to keep the Trumpite hordes at bay, appeasing them with his anti-anti-Trump position so they don’t turn their ire against him. The task of standing up to McCarthy was left to people other than Irving Kristol, just as the fight against Trumpism will have to be waged without the help of William Kristol.

Now, of course, Kristol feels differently—now that it's too late. But it's impossible to understand what he feels today without placing it in the larger context of how he has tried to double-deal reality in the past. Kristol has repeatedly tried to place dim bulbs at the forefront of American politics, to play that role, and had remarkable success in elevating some to prominent positions. But he's never gotten any of his Frankensteins close to the presidency. With Donald Trump as the presumptive nominee, suddenly Kristol worries about the future of the party. But it's the Palins and Quayles he elevated that helped build the GOP's know-nothing wing.

Naturally, the last thing Kristol will to do is take responsibility for what he's done. Personal responsibility is for losers. On that, Trump and Kristol still entirely agree.