If you've ever worked with legacy systems older than 10 years, you'd notice that they become a victim of their own "success". You can't throw away features added over years, because a lot of users depend on it, and if you tried to rewrite it, you'd have to rewrite bug-to-bug.
I worked on such systems, and I did try rewriting, and gave up because of sheer volume of work and the knowledge of institutional lore that was required to do it. On the other hand I'm currently embarking on our startup's "rewrite" and things are much much easier, because the feature set is small and I can freely throw away stuff that didn't work.
See also, http://en.wikipedia.org/wiki/Gall's_law