This question is about the semantics of glues like 0pt plus -1fill, where the coefficient in front of the fill is negative. The following minimal example shows my attempt to figure this out empirically:
\documentclass{article}
\begin{document}
\noindent
\framebox[80pt]{\hskip 0pt plus 1fill 2 \hskip 0pt plus 2fill} \\
\framebox[80pt]{\hskip 0pt plus 1fill 1 \hskip 0pt plus 1fill} \\
\framebox[80pt]{\hskip 0pt plus 1fill 0.1 \hskip 0pt plus 0.1fill} \\
\framebox[80pt]{\hskip 0pt plus 1fill $-0.5$ \hskip 0pt plus -0.5fill} \\
\framebox[80pt]{\hskip 0pt plus 1fill $-1$ \hskip 0pt plus -1fill} \\
\framebox[80pt]{\hskip 0pt plus 1fill $-2$ \hskip 0pt plus -2fill} \\
\framebox[80pt]{\hskip 0pt plus 1fill $m2$ \hskip 0pt minus 2fill}
\end{document}
Here's the output:

Comparing the -2 and m2 lines, we see that plus -2fill really is different from minus 2fill. The -0.5 line makes sense to me. I said I wanted the ratio of the two spaces to be -0.5, and it looks like tex made it so. The space on the left-hand side is positive, while the space on the right-hand side is negative and about half as big.
What I don't understand is the results for -1 and -2. They don't seem to extrapolate logically from the preceding examples. Is this just some kind of artifact of the internal implementation of the data structure, like an integer overflow or something?
-------------- material added later -------------
After playing with this some more, I think I understand it at least a little better. This code produces the following output.
\documentclass{article}
\begin{document}
\newcommand{\foo}[1]{%
\noindent{}$#1$\hfill%
\framebox[20pt]{\hskip 0pt plus 1fill{}.\hskip 0pt plus #1fill}%
\hfill\par%
}
\foo{-0.5}\foo{-0.6}\foo{-0.7}\foo{-0.8}\foo{-0.9}\foo{-1}
\foo{-1.1}\foo{-1.2}\foo{-1.3}\foo{-1.4}\foo{-1.5}
\end{document}

This makes sense because it's trying to place an amount of whitespace L on the left and R on the right such that L+R=w and R/L=x, where w=20 pt and x is the number such as -0.5 in the above code. The solution of these equations is L=w/(1+x), which is what we see graphed. What is still a little odd to me is how it handles x=-1, for which there is no solution.
related: Mathematical description of TeX's infinite numbers?
-0.85it is quite near the right margin. – samcarter_is_at_topanswers.xyz Jun 23 '14 at 15:33plusrefers to the stretching component,minusto the shrinking component; the shrinking component is disregarded if the text has to be stretched and conversely. Soplus -2fillandminus 2fillhave nothing to do with each other. – egreg Jun 23 '14 at 15:42\framebox[20pt][s]{...}so the implicit centering glue (offilorder) is not inserted at either end of the box (see fifth example in my answer, where I added some words). – egreg Jun 23 '14 at 18:27