Donald Trump caught various West Wing officials off-guard on Tuesday when he decided to describe the woman alleging that they’d had an affair as having a “horseface.” But privately, the president not only thought that it was strategically smart to go after the adult film star Stormy Daniels in such a visceral way; he workshopped the insult prior to tweeting it.

Well before Trump mocked Daniels’ physical appearance, he trial-ballooned the “horseface” dig privately—among White House aides, close friends, and acquaintances. One source close to Trump even recalled him saying in passing, “that fucking horseface.”

The president often tosses around ideas for snide new nicknames in smack-talk sessions with associates, if only to gauge their reactions. And, as in past cases, the “horseface” incident saw Trump defying presidential norms (whatever those are anymore) and ignoring senior aides and confidants who advised him simply to let the matter go.

According to a White House official and two other sources who talk regularly to Trump, many people in his orbit had for months told the president it was best not to elevate Daniels by, for example, rage-tweeting about her. Trump, for his part, argued that hitting back publicly and “hard” at the porn actress would not only be right, but could prove politically advantageous.

That’s the lesson he’d drawn from prior instances in which he’d chosen to counter-punch, even in the context of petty feuds deemed beneath the dignity of the presidency or schoolyard-style taunts aimed at brutal dictators.

In the days leading up to his first speech before the United Nations, for instance, Trump asked senior officials and friends if they thought it was a good idea for him to call North Korean leader Kim Jong Un the “rocket man” or “little rocket man” during his speech, according to two sources with knowledge of these conversations. He even told some people that others had advised him that such a move would be unwise and unnecessary, even though he thought it would be “smart” and effective branding.

Despite the chorus of official and informal advisers urging the president to forgo the moniker, Trump did it anyway, declaring before the UN General Assembly last year, “Rocket Man is on a suicide mission for himself and for his regime.” He went on to warn that the United States was ready to "totally destroy North Korea," if it came to war.

The president came away from that moment relishing the “rocket man” headlines and hoopla, viewing it as a great triumph. In the months that followed, Trump would playfully and repeatedly tweak his advisers who told him not to utter “rocket man” during his debut UN speech.

“They love it—love it—when I fight. It’s great,” Trump told people around him in recent weeks, according to a participant in the conversation. He was referring to his conservative base voters.

When it comes to Daniels—who has taken Trump to court in a legal drama that has exposed a cover-up and potential campaign finance violation—the instinct has been invariably the same even if, by Trump standards, the tweet was viewed as a bit reckless. One source who has been with President Trump as he privately tests out nicknames and put-downs he’s considering told The Daily Beast that “horseface” is “one of the wildest nicknames so far, that’s for sure.”

The insult stems back to allegations that Daniels and Trump engaged in a consensual affair, during which Trump was married to his third (and current) wife and had recently fathered his youngest child. As the 2016 campaign was coming to a close, Daniels was paid to keep her story quiet. When reports of that hush money arrangement leaked out, Trump world became embroiled in a series of legal and public-relations headaches.

Those only worsened when Daniels decided to get out from under the non-disclosure agreement and, ultimately, began discussing the alleged affair with Trump. In graphic detail, she’s recalled how Trump had an unimpressive penis, comparing its size and appearance to Toad from Mario Kart. She didn’t miss the opportunity to use Trump’s tweet on Tuesday to remind her followers of those details.

“Ladies and Gentlemen, may I present your president,” Daniels tweeted in response. “In addition to his...umm...shortcomings, he has demonstrated his incompetence, hatred of women and lack of self control on Twitter AGAIN! And perhaps a penchant for bestiality. Game on, Tiny.”

Such an exchange is almost certainly unprecedented in U.S. political history. And among Trump’s prominent allies on media organs like Fox News and Fox Business, it appeared no one knew just how to react. Those who did weigh in, however, were mostly supportive, even enthusiastically so of Trump’s “Horseface” Twitter salvo.

Corey Lewandowski, Trump’s former campaign manager and a current outside adviser, said on Fox Business on Tuesday, “She's attacked him so many times and what he did was he responded in kind.”

“He's a great counter-puncher, and now people will always think of her as ‘Horseface,’” he added. “Because he has this magical ability that when he gives someone a nickname, it sticks with them for the rest of their lives. Now she'll be Stormy ‘Horseface’ Daniels forever.”

Jesse Watters, a Fox News host and a friend of President Trump’s, expressed similar sentiments on The Five on Tuesday evening.

“Now all of a sudden [the left is] clutching their pearls when the president says the word ‘horseface.’ Please,” he said. “To be surprised now that Donald Trump says bad things and uses dirty nicknames about people three years later either you haven't learned a thing or you're just dense. This is what he does and this is how he wins.”

Even some of the president’s conservative Christian supporters were more than willing to publicly argue that Trump’s “Horseface” strafe was just another example of his strong pugilistic instincts—even if physical insults don’t quite jibe with Christ’s teachings.

“I would naturally not condone any type of the language that would be [used] berating another human being, but yet, I do understand that [with] Stormy Daniels—clearly attention-seeking, clearly wanting to take the situation and wanting to profit from it, she is in the adult industry,” Mark Burns, a pastor who campaigned for Trump in 2016, told The Daily Beast. “‘This person came after me so now I’m gonna come after them’...That’s not what I would teach, as a pastor...But that’s his character, and it’s one of the things I believe has made him successful as a president and as a politician.”

But Trump’s comment comes with obvious risk too. At a time when Republicans are desperately attempting to hang onto female suburban voters, GOP officials have recoiled at Trump’s repeatedly vulgar and degrading comments about women.

Recent polls show that Democrats have made inroads among married, white, college-educated women, many of whom traditionally vote Republican but live in districts that Democrats are hoping to pick up in November.

In what’s become a normal occurrence following many of Trump’s remarks, Republicans mostly ignored the president’s language. Those who did weigh in to condemn it happened to be on their way out of elected office.

“To say this is unbecoming of any man, let alone the POTUS, is a vast understatement,” retiring Rep. Ryan Costello (R-PA) posted to Twitter. “And to say this enables teenage boys to feel they have a license to refer to girls [with] such names is obvious. It’s all very embarrassing.”

The president, by his own words, couldn't care less if Costello and others find it embarrassing. In an interview with the Associated Press, when asked if his conduct was appropriate, Trump replied, “You know what? You can take it any way you want.”