Donald Trump might be the worst president in American history, but with his incompetence, belligerence and intellectual deficits come a perverse advantage: it’s tough to shame someone who has no shame; it’s hard to hold a man accountable for a lie when he doesn’t care if he’s a liar; you can’t chasten someone for breaking the rules when he never believed the rules applied to him.

But while Trump has snaked and slithered his way in and out of scandal, corruption and self-dealing his entire life, there’s one force that seems to truly destabilize him: a competent woman. Which is why, in the Trump era, there’s no better speaker of the House than Nancy Pelosi.

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This week, the simmering Trump-Pelosi conflict ratcheted up another notch as the president declared that he will indeed give the State of the Union as scheduled on 29 January, despite a request from Pelosi that he delay, given the ongoing government shutdown and security concerns it poses. Pelosi volleyed back hours later, writing that lawmakers “will not consider a concurrent resolution authorizing the president’s State of the Union address in the House chamber until government has opened”.

Whether the president actually does speak on Tuesday or not, this will not be the last time he and Pelosi face off.

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Luckily, she has the upper hand, and not just because she’s smarter and more experienced than the president (although she is) or because she knows his job better than he does (although she does). She’s also a foreign creature to him.

Trump has spent the whole of his personal life surrounding himself with a particular type of woman: young, working hard at being attractive to men, and compliant. He filters the women in his professional life through this same lens, demanding unyielding female loyalty and prizing female beauty.

As each of his wives grew older and more assured, he replaced them with someone younger and more dependent on him. He dedicated a significant amount of time and money to beauty pageants, where he was accused of being a serial sexual harasser and clearly enjoyed the spectacle of young women parading for male approval (and judgment). His own daughter has seen career success thanks to his money and connections, and yet his first impulse is always to brag about her good looks. He comments leeringly on the physical appearance of reporters and first ladies.

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To Trump, a woman’s worth is measured by her sex appeal, and age knocks some points off – no doubt because, for many women, age also increases confidence and conviction. Trump “loves” women, but really, he loves it when women play along with his fantasies of what a woman should be. He simply does not consider women peers and equals. Just look at his cabinet: he’s appointed twice as many men as women. Day to day, he’s surrounded by advisers who are almost entirely white and largely male. As far as diversity goes, there are as many men named “Alex” in Trump’s cabinet as there are women with brown hair.

He is also particularly appalled by women who don’t go out of their way to compete for male attention – and enraged by women who challenge men directly. When Carly Fiorina ran in the Republican primary, he told Rolling Stone: “Look at that face. Would anyone vote for that? Can you imagine that, the face of our next president?” He added: “I mean, she’s a woman, and I’m not supposed to say bad things, but really, folks, come on. Are we serious?” His vitriol toward Hillary Clinton is well-documented, and went far beyond normal political sparring. His attacks on female detractors inevitably zero in on their looks.

Aside from insults, he doesn’t really know how to deal with assertive older women

But aside from insults, he doesn’t really know how to deal with assertive older women, because for his entire life they have existed outside of both his immediate view and his broader imagination. When he talks about “women”, it’s obvious that only a small subsection of us fit into his definition; some might have qualified, but by virtue of challenging him can be written off as bimbos; a few others are witch-like hags who have surrendered their claim to womanhood; and the rest are simply invisible.

The women of Trumpworld have a single role, and that is to say “yes”. Trump has long bought and paid for that acquiescence. Now, Pelosi is telling him no, and she has real power and can’t be ignored, replaced or waved away. They aren’t in direct competition (as he was with Clinton and Fiorina), so he is less able to leverage more generalized public sexism to win his battle against her. He’s used to women helping him feel like a big man. Now, here’s a woman who makes him look small and impotent.

Which is why Trump will respond the only way he knows how: with feeble insults and exclamation-point-laden letters. Pelosi will play it cool. She knows how the rules work and how the system operates, and she’s no stranger to condescending men who insult her before they vastly underestimate her.

Trump, on the other hand, has never had to work directly with a woman like Pelosi, and seems completely perplexed by her behavior, which is so different from that of all the other women in his world. She knows what she’s up against. He can’t seem to tell what species she is. And it usually ends poorly for the man who can’t tell a kitten from a lion.