Holy Boycotts - Permitted, recommended, obligated or forbidden?

Question

It is a well known principle that we must make sure that the people we give tzeddakah to are definitely poor and not scammers/fraudsters (see Yoreh De'ah 251:10).

I am sure this principle is not directly related to my question, but in general, Torah makes it a moral imperative that we should be careful who we give our money to. If giving our money to a thief is so questionable, then what about giving our money to businesses whose conduct is immoral?

In this case, it is not tzeddakah; they are giving us a service or product which we are paying for. However, by providing them with a profit, they are able to continue and even grow their operation, and more immoral conduct will take place. One is also, in theory, showing support for them, which raises questions of chillul Hashem.

There are 3 general levels to this question. I am personally most interested in the last, weakest case and will award the bounty to whoever can answer, but would also be keen to see answers for the other cases.

Strong case of immoral conduct

A typical example would be a company that is known to use terrible working conditions in what is effectively slavery. A pretty uncontroversial example is the granite counter-top industry, or the construction industry in Dubai.

Case of conduct antithetical to Torah hashkafa

Another example might be a company who donates to causes that are not aligned with Torah, such as gay marriage, late term abortion, transition surgery for minors.

More subtle cases of political issues

More subtle examples might be companies that support a political party that is anti-Israel, or in favour of anti-Torah policies, or who deplatform Jewish or Torah-aligned speakers (for their alignment with Torah) or who themselves boycott Jewish institutions or Israel; companies that pollute and wreck the climate or don't pay tax, or it has been claimed that they discriminate against race and sex etc. I.e. things that can get quite political, and we can't really be completely sure what is really going on, in today's crazy political confusion.

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What is the halacha for doing legitimate business with such companies? How exactly should we arrive at the conclusion of which companies are aligned with Torah and which are not?

NOTE: I am not looking for an itemized list of all possible evils a company can partake in and a yes/no for each - the examples given are just to help explain the question. I am looking for general support/lack of support and discussion regarding the principles of doing business with immoral businesses, to whatever level of detail is available. Thank you.

Answer 1

Strong Immoral Conduct

"It is forbidden to buy a stolen article from a thief. This is a severe sin, for it reinforces a transgressor and motivates him to steal in the future" (Rambam, Theft 5:1)

Case of conduct antithetical to Torah hashkafa

"On the three days before the festivals of gentiles, it is prohibited to engage in business with them" (Mishnah, Avodah Zara 2a)

More subtle cases of political issues

The Gemara asks later what's the reason for the prohibition against conducting business with them. "Is it because of profit (Rashi - and he will subsequently give thanks to his idol) Or perhaps it is because 'you shall not put a stumbling block before the blind' (Rashi- he'll use the animal you sold him for worship)" (Avodah Zara 6a).

It would seem, if the subtle political issue is halachically problematic for the business owner, then one should refrain from doing business with them.

Answer 2

Regarding what you called the most subtle case. Here's what I can find in Sefer haMidot, and I think it answers that case. Basically if your mind is there then you already ought to consider where the money comes from and where it goes and be conscientious to the extent possible.

Likutei Etzot - Mamon u'parnasah

10. "There is also another rectification for the desire for money, which is to look at the root from which all money and its influences come. Through contemplating this, one's desire is nullified, for there in its root, all influence is pure, clear light, and spiritual pleasure, and there is no desire except for that which is connected to holiness. And who is foolish enough to abandon spiritual pleasure and take material pleasure in its place? But this contemplation is impossible to achieve until one rectifies their covenant, as it is written, 'And from my flesh, I behold God,' as in the beginning, one must rectify the holy flesh, and then they can look upon Godliness. And for this reason, the essence of the rectification of the desire for money is through the covenant, and when one rectifies their covenant, it is impossible to fall back into the desire for money" (Likutei Moharan, 23:5).