What makes the situation with these wheels so much more drastic than
what happens with python-virtualenv already?

https://packages.debian.org/sid/all/python-virtualenv/filelist

I don't understand why there needs to be an entire effort de-bundling
and de-(re-?)-vendoring files and why this hasn't been applied to
virtualenv as well?

With the `--without-ensurepip` flag on, the code is only used in
isolated venvs, so it can't effect the system.

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https://bugs.launchpad.net/bugs/1290847

Title:
  pyvenv fails due to mising ensurepip module

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