> a blacklist is less work than a whitelist

No, it isn't. It's so much more tremendously difficult that I don't think it can reasonably be done that way. Do you have any idea how much software is in PyPI? There is no requirement for any package to use any trove classifier, or to list any license. So checking these would not be enough. You would have to manually check every other package for the license to see if it needs to go on the blacklist. And as new software gets uploaded, you would have to keep doing this. Any package not getting caught would completely undermine your efforts.

If you instead just whitelist based on classifiers, and possibly secondarily by recognizing particular license strings, you wouldn't need to worry about it. A package being wrongly assumed to be proprietary because it doesn't have a proper classifier on it wouldn't be a disaster.

> The Linux Libre kernel blacklists non-free bits, so why can't our custom pip?

Apples and oranges, my friend. PyPI is a software repository containing some proprietary software, not a program with blobs in it.

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