I wouldn't go so far as to say it's never come up; it's something I've thought about a number of times, and I've waffled on it a few times.

It's not fundamentally unreasonable to want it to adapt to the current terminal window, though I think it would be in a minority among the Unix command line tools that I use.

Raymond's point about potentially confusing students is an important one, though.  If adaptive behavior is sufficiently desirable, the module should check the value of an environment variable, and default to the current behavior.  PYTHONADAPTIVEPPRINT ?