Well, AFAIK it's not clear that in the US the courts have the right to compel someone to modify their software in that way. The FBI holds that it does, but so far it's been fought and they've given up when they've tried it. I think if such a thing were to happen, the fundamental ability to secure any software goes out the window. Even package signing, etc go out the window because they can just compel you to produce new software, signed with your existing key.

But let's step back a moment and presume that they do have that ability to compel. The first step here is that none of the PyPI Administrators are the legal owners of PyPI, so such an order would not be sent to any of us, but rather to the PSF itself. The PSF would then be on the hook to either comply or fight said hypothetical order, but individual members of the administration team would not be, and would be free to quit. They may not be able to say why they've quit, but quitting AFAIK would be entirely possible.

The PSF, while not having Apple's war chest, does retain counsel for dealing with things like this, and I can say personally I'd spend myself broke before I'd be willing to do so.

We are going to be implementing signing, and I'm hoping we'll be able to make strong progress on that soon.