AI Experiment

Karoline Leavitt's response to the reporter's question as to how the White House decided Jared Kushner's involvement in all the Middle East negotiations was appropriate kind of triggered me:

It may be frankly, but it's not despicable. It's what we call *normal*. The reporter isn't suggesting it's inappropriate, he's presupposing that any normal person would regard it as inappropriate prima facie.

[image or embed]

— Yastreblyansky (@yastreblyansky.bsky.social) July 22, 2026 at 8:40 PM

But am I right on that? Is it really prima facie inappropriate? It seems obvious to me and my Bluesky pals, but then of course I and they don't like Trump or Kushner. We think they're horrible and criminal malefactors. So we could be biased.

So I thought I could put it to an LLM test: If I put it to Google's Gemini as a pure hypothetical case, the way they do in in law school, at least in the movies I've seen, without any names, what would it say?

suppose the president of a country invites his son-in-law to join a diplomatic negotiating team dealing with parties some of whom have given the son-in-law's investment firm billions of dollars, while the other parties haven't given him anything. Is that appropriate?

The LLM responded, and I'll give you the whole thing, in the purest LLM style (note the em-dashed parenthetical and the bullet list):

Such an arrangement constitutes a severe ethical breach and a massive conflict of interest. Mixing official government diplomacy with a family member's personal investment firm—especially one heavily funded by foreign governments that stand to gain from those negotiations—is widely condemned by government watchdog groups. [1, 2, 3]

The situation presents several major ethical problems:

Self-Enrichment: Having a relative use an official government position to negotiate on behalf of foreign entities that have funneled billions into their private equity firm blurs the line between public service and personal financial gain. [1, 2]
National Security Risks: Critics and ethics experts have repeatedly stated that a diplomat cannot fairly and objectively represent their country's national interests while acting as a financial beneficiary of the very foreign governments with whom they are negotiating. [1, 2]
Nepotism: Appointing family members to influential government roles violates the spirit (and often the explicit statutes) of anti-nepotism laws designed to prevent corruption and ensure government officials are appointed based on qualifications rather than personal connections. [1]
Skewed Negotiations: Even if the son-in-law does not let the investments impact his decisions, the appearance of a conflict fundamentally undermines the integrity of the diplomatic process. The parties that haven't invested are placed at a disadvantage, and the public is left with no way to verify whether foreign policy is being dictated by national interests or the financial interests of the president's family. [1, 2, 3]

So take that, Karoline. You are so utterly wrong, and of course dishonest; the real answer to the question would be something like, "Nobody dared to suggest that it might be inappropriate because President Trump might have gotten mad at them, and definitely wouldn't have changed his mind. If he wants Kushner, he gets Kushner, no matter what it looks like from outside."

And it's extremely categorical and fulsome, not waffling and skimpy like ChatGPT, which merely says

This situation raises ethical concerns regarding conflicts of interest and nepotism. It may be perceived as inappropriate for the president to involve a family member, especially one who has financial ties to certain parties in the negotiations, as it could undermine the integrity of the diplomatic process and lead to biased decision-making. Transparency and the avoidance of conflicts of interest are crucial in diplomatic negotiations to maintain trust and credibility among all parties involved.

(the "may be perceived" and "could undermine" show how frightened it is of taking a position), and is unable to offer corroborating sources, unlike Gemini, which is a big reason why I use Gemini, which always gives you something, from the traditional Google search engine, though it may be wrong, and is maddeningly more likely to send you to (Google-owned) YouTube rather than material published by more respectable means (the LLM itself blames this in part on its being programmed to avoid paywalls and copyright material; it acknowledges that Claude is better on this, but as far as I can tell Claude won't do anything I want for free). 

It's pleasing to me that Gemini doesn't seem to know (or "know") at all that I'm asking about the Trump-Kushner case, and accepts my presenting it as just a hypothetical—if only because it makes me feel I formulated the prompt pretty well. But also pretty interesting, because the cited sources are all about Trump and Kushner anyway. 

You can see why, because the Trump-Kushner material is the only instance you can find of corruption this blatant in a society that has supposedly adopted the rule of law. I mean, did Ferdinand Marcos or Mobutu Sese Seko or one of their relatives ever accept a huge bribe in such a public fashion? Their advisor Paul Manafort certainly would have advised them not to, as he also would have done with his Ukrainian client Viktor Yanukovych if necessary,  but I think Yanukovych didn't need the advice either—only Trump, in his second outing, refusing advice from anybody. (Manafort has new clients in the Bosnian enclave of Republika Srpska and in Albania, the latter of which has recently shown up in a dreadful Kushner project.) Trump and Kushner were uniquely relevant to my prompt because nobody else has ever tried to do it so shamelessly.

But it's also an interesting illustration of the inhumanity of the LLM that it doesn't need the real-world examples, that it can carry on the discussion at such an abstract level, even when it's got all the examples, extremely salient ones, in its pocket. Like a survivor from the age of Descartes and Kant, as if it didn't want to lower itself. Am I reading that right?