Given there is no ! operator in Python, I next tried ~ (despite that I'm after a logical not). This came as a surprise:

>>> bool(~True)
True
>>> bool(~False)
True
>>> bool(~~False)
False
>>> ~True, ~~True, ~False, ~~False
(-2, 1, -1, 0)

Is there any consideration to "fixing" this? Is int(True) 1 due to C? Why is it preferred over -1?

It seems more appropriate to me that True have:

def __invert__(self): return False
def __int__(self): return 1 # or even -1

This also "fixes" this case too:

>>> -True
-1

Did you try the "not" operator?
http://docs.python.org/reference/expressions.html#boolean-operations

>>> not True
False
>>> not False
True

This is deliberate, and will not be changed (at least not until Python 4, and likely not even then). Please ask on a Python forum about history and motivation of the boolean type in Python if you want to know more.