Apple's documentation states that by default the controller and window aren't deallocated, because it's useful to not have to reload everything, which makes sense. But their documentation goes on to say that you can override that behavior, but not explain how.
Apple's Docs:
When a window is closed and it is part of a document-based
application, the document removes the window’s window
controller from its list of window controllers. This results
in the system deallocating the window controller and the
window, and possibly the NSDocument object itself. When a
window controller is not part of a document-based application,
closing the window does not by default result in the
deallocation of the window or window controller. This is the
desired behavior for a window controller that manages something
like an inspector; you shouldn’t have to load the nib file
again and re-create the objects the next time the user requests
the inspector.
If you want the closing of a window to make both
window and window controller go away when it isn’t
part of a document, your subclass of NSWindowController
can observe the NSWindowWillCloseNotification notification
or, as the window delegate, implement the windowWillClose: method.
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