The gospels do indeed whitewash the relationship between Rome and Judaism because they were written after the destruction of Jerusalem. It was no longer cool to side with the Jewish militants, so the Jewish messiah had to be spiritualized. Hence, Christianity.

Still, Jesus's countercultural message shines through, as twisted as it might have been for all sorts of political and propagandistic reasons. For instance, "turn the other cheek" makes for a condemnation of Roman imperialism and war, not to mention of punishments like crucifixion. And "the first will be last and the last will be first" makes for a condemnation of the conventional social hierarchies. He didn't just say it's good to be poor. He said it's impossible for rich people to go to Heaven since they become attached to their wealth. Jesus hung around with a female prostitute and treated women as equals, or on an individual basis, so he wasn't exactly pro-patriarchy, contrary to the Roman Empire.