Let me ask in a different, though related, way:
When the halakhic decisor or interpreter comes to interpret a given Talmudic passage, does he come with his own conceptions and assumptions? Put differently, if a certain Jewish law stands in tension with the decisor’s philosophical outlook, will he (even if subconsciously) interpret it differently rather than simply according to its plain sense? In other words, what place do my basic outlooks have when I encounter a sugya?
A somewhat different formulation: behind a given halakhic (or legal) determination, are there only internal halakhic explanations (that is, interpretations of ancient sources), or also philosophical/intellectual/ideological explanations? I see a problem with the second possibility, because an “explanation” means a necessary and sufficient reason. Therefore, if there is an internal halakhic reason for a certain law, why look for another reason (namely, the philosophical outlook)? That’s Occam’s razor.

Or let me put it this way:
We all agree that the decisor comes with his prior assumptions; he brings himself (which is shaped by his upbringing, etc.) to the sources. That’s simply a fact. But my question is whether he ought to make a special effort to neutralize the influence of his outlook on his interpretation of the text?

An explanation provides a sufficient reason, but not necessarily a necessary one. A decisor’s outlook certainly finds expression in his interpretations and rulings. Who would even dispute that?
And he certainly does not need to neutralize it. That is his outlook. Of course, there is always a balance against interpretive honesty.

Would you be okay with an interpreter whose outlook tells him that homosexuality is fine and permitted and all that, and he manages to interpret the halakhic sources in such a way that they come out permitting homosexuality—wouldn’t that be suspicious in your view? Even if his interpretation is, say, plausible, maybe he’s being misled by his outlook, no?

Absolutely. That is just a particular case of what I wrote. As long as his interpretation holds water (in his view).

Regarding the categorical difference between Jewish law and morality,
what stands behind any given halakhic law? Do the Torah’s laws reflect an ideology or different ideologies? Put differently, can one know, from the fact that the Torah commanded such-and-such, that the Torah advocates, for example, a communist/capitalist ideology, or a feminist one, etc. etc.?
That is, does the question, for example, “Is the Torah misogynistic?” have any meaning or not? And if people answer, “Yes, because only the husband acquires and divorces, a cheating husband is no problem, it says ‘who has not made me a woman,’ etc.”—are they right?

What stands behind the law “put on tefillin” / “write a ketubah when you marry” / “an unpaid bailee is exempt from theft” / “a married woman is liable to death, but a cheating husband is no problem” / and so on and so on with all the laws?
Is there a logic behind them that can be pointed to?
Is the Torah only a system of laws that teaches us no ethical/moral/judgmental/other lesson, or does the Torah want us to draw ethical/ideological/moral/philosophical conclusions from the laws it commands us?

In general, in my opinion, one cannot derive general principles from the laws. In most cases where I’ve seen people do this, it’s just homiletics. An economic outlook depends on common sense and should not be sought in Jewish law.
That Jewish law discriminates against women is true, and there is probably some conception behind it of the woman’s role in society. But in most cases these are laws shaped by the Sages and not by the Torah itself (even when we’re talking about Torah-level laws), and therefore one should not derive general principles from them either. The status of women has changed, and even if there are laws concerning which we have no authority to change them, there is neither any necessity nor any logic in drawing from them ethical and principled conclusions.

Okay, but is there logic behind the laws, even if we cannot understand it because of our limitations? In purely Torah-level law—for example, the prohibition of interest— is there some logic/ideology/philosophy behind it, or is it just an arbitrary decree?

I assume there is logic and purpose behind every commandment. But attempts to get at them are usually highly dubious in my eyes. Beyond that, most Torah-level Jewish law as we have it was created by the Sages and not from the Torah itself, and I already noted that above.

Here, for example, in Column 503 you inferred from halakhic sources that the correct philosophical outlook is tolerant monism. Does that mean one must be a tolerant monist philosophically? And if I think the truth is that one should be a pluralist, and I also think you are right that from halakhic sources a tolerant monist outlook emerges, what am I supposed to do?

I am not talking about general tolerance but about the meta-halakhic approach. I proved there that in Jewish law the correct approach is tolerance. That does not mean this is the approach in other areas unrelated to Jewish law. There you should follow your own reasoning.

Rabbi, I feel a bit unsatisfied with the discussion above. I wanted to go over a few points with you that I didn’t fully understand:
1. What is the meaning of the separation between Jewish law and morality, if moral considerations sometimes stand behind Jewish law? You see here that Jewish law can be derived from morality, and if so one can learn morality from Jewish law.
Is there a difference here between rabbinic law and Torah law?

You explain that in matters of fact there is no formal authority, whereas in norms there is. But what does that mean, since behind a norm there stands some fact—some ideology? Obviously, when the Holy One, blessed be He, commands me to do X, He is not merely commanding me to do X like a robot, period; rather, He wants me, when I do X, to internalize the ideology, the value judgment, that stands behind X. But we already saw that ideologies have no authority, and if I don’t identify with one then nothing in the world can change that. And this is connected to the question of hermeneutics: when I see that the Holy One, blessed be He, commands me to do X, can some ideology be inferred from that?

I’d be very grateful if you could clarify this for me.

1. Moral considerations do not stand behind the laws. Sometimes, when there are two interpretive options, we choose the one that accords with morality.
2. You are assuming several unfounded assumptions here. In Jewish law we do not generally derive the reason for the verse, and from this it follows that it is incorrect to say that the purposes of the laws must be known to us and cause us to adopt certain outlooks. Factually, that is not true. The Holy One, blessed be He, has reasons and purposes for which Jewish law was created, but those are His considerations, not ours.

In your view, can Jewish law regulate the day-to-day life of the Jewish people while containing no moral principles and moral norms?
If the Holy One, blessed be He, wanted the Jewish people to conduct themselves according to Jewish law, and nothing else is needed for the Jewish people to live in an orderly way like any other nation, that means that in order to achieve social order we do not need moral or legal rules (since in Jewish law the principles and considerations are not moral or legal but religious and metaphysical)??

I’m not even beginning to understand this strange question. Jewish law and morality together regulate the life of the Jewish people. But why identify the two?

The role of morality is not to regulate social life. Otherwise we would legislate it.
A legal system comes to achieve social order that will exist even if the members of society are not morally upright people in their hearts.

Jewish law is sufficient to run a proper society (even if there were secular law, there would still be Jewish law, and the Jewish people would be supposed to act by it, so it can regulate social order).
Behind Jewish law there do not stand moral principles (unlike behind any legal system, where one can find moral principles).
Conclusion: here is an amazing phenomenon—a proper society can exist even without morality.
It is not plausible that a society can exist without morality.
Conclusion (by negation): certainly moral considerations and moral aims stand behind Jewish law, and not only religious aims. QED.

Come on! Where does this pilpul come from? Moral rules are needed together with Jewish law, and the way they operate is such that they do not require legislation and enforcement. What does require enforcement will enter through Jewish law, or in some cases the Sages will bring it into Jewish law (we compel against the trait of Sodom, and the like).

Is the purpose of the Torah’s laws (both prohibitions and civil laws) to achieve justice (human, social, moral, universal, etc.)?
If so, then when there is a conflict between morality/justice and Jewish law, apparently I should correct my conceptions of what is just.
And if not, then what is their purpose at all? Or if you prefer: are the commandments arbitrary?

You asked exactly this in a parallel thread and I answered there. Their purpose is religious values, not justice in the sense accepted by us. I referred you to Column 15, and to the beginning of the third book of the trilogy.