I am currently looking somewhat carefully at how TeX manipulates skips, and I am having trouble finding practical use cases for skips with a negative stretch or shrink component, such as \Askip and \Bskip in the following.
\newskip\Askip
\newskip\Bskip
\Askip 0pt plus -2pt minus 3pt
\Bskip 0pt plus 1fil minus -4bp
They lead to odd situations. For instance, putting a skip with a large negative stretch component in a box that it somewhat underfull will cause other skips to shrink proportionally to their stretch component.
\hbox to 200pt{A B C\hskip 0pt plus -50pt}\bye
What happens is that since the box is underfull, TeX looks at the sum of the available stretch components. Since this sum is negative, the stretch components are multipled by a negative number.
So, obviously this example is not useful, but are there some more useful examples of what negative glue can be used for?

\hfilnegand\vfilneg(where the shrink component is infinite). – egreg Mar 6 '12 at 13:56