One thing that would help Python in this "debate" (or, perhaps simply put it in the running, at least as a "next Java" candidate) would be if Python had an easier migration path for Java developers that currently rely upon various third-party libraries. The wealth of third-party libraries available for Java has always been one of its great strengths. Ergo, if Python had an easy-to-use, recommended way to use those libraries within the Python environment, that would be a significant advantage to present to Java developers and those who would choose Ruby over Java. Platform compatibility is always a huge motivator for those looking to migrate or upgrade.
Personally, I'm using Andi Vajda's JCC for this purpose. Recommended. The nice thing about it is that it turns jar files into Python modules; you don't need the source.