i don't think typing was the issue. at the time there didn't exist any typed languages that were as easy to use as python or ruby. (ok, not true, there did exist at least one: pike (and LPC which it is based on). pike failed for other reasons. otherwise if you wanted typed your options were C, C++ and then java. none of which were as easy and convenient to use as python or ruby. java was in the middle, much easier than C/C++, and that did catch on.