> However, in the case of assertions, a nice and secure feature of Python has 
> been lost without any apparent benefit.

It's always been possible to have side effects from an assertion:

>>> always
Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
NameError: name 'always' is not defined
>>> def f():
...     global always
...     always = True
...     return True
... 
>>> assert f()
>>> always
True

The walrus operator just adds another way to do it.
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