IWBNI you could write it like this:

   with (open('/etc/passwd') as p1,
         open('/etc/passwd') as p2):
         pass

This seems analogous to using parens to wrap long if-statements, but maybe
there's some subtle corner of the grammar that makes this problematic (like
'with' treating the whole thing as a single context manager).

Of course, you can wrap with backslashes, but ick!