What is more, the Church’s foundation documents (to say nothing of its Founder himself) were notoriously on the wrong side of history. The Gospel was foolishness to the Greeks, said St Paul, and a scandal to Jews. The early Christians got a reputation for believing in all sorts of ridiculous things such as humility, chastity and resurrection, standing up for the poor and giving slaves equal status with the free. And for valuing women more highly than anyone else had ever done. People thought them crazy, but they stuck to their counter-cultural Gospel. If the Church had allowed prime ministers to tell them what the “programme” was it would have sunk without trace in fifty years. If Jesus had allowed Caiaphas or Pontius Pilate to dictate their “programme” to him there wouldn’t have been a Church in the first place.
–N.T. Wright, Women Bishops: It’s about the Bible, not fake ideas of progress
David W. Swanson 
Wright misuses the phrase, I think. It (“on the wrong side of history”) is not commonly used to mean that a position is “in line with it’s contemporaries”, but quite the opposite, means that the view may not be popular contemporaneously, but over time (i.e., “history”) is proved to be victorious. In this sense, history now looks at many of the then controversial teachings of Jesus and says that he was on the right side of history – just at odds with the contemporaries around him who refused to change.
Gender equality, care for the poor, justice, mercy, the end of slavery, opposition to religious dogmatism, opposition of oppression – these were Jesus’ ideals that garnered him so much anger by the contemporaneous “powers that be”. But history has shown these ideals to be the winners over time of where society and civilization is trying to go (with many shortfalls, setbacks, and much ground to gain, still, no doubt). So Jesus was on the right side of history in the sense that that phrase is most commonly used – that is, on a larger timescale than the contemporary events.
Further, on issues like gender (and, birth control and homosexuality) the tables now appear to turn where Jesus was still on the right side of history (in being progressive, inclusive and expansive on these issues), whereas the contemporary church has now taken the role of the Roman & Jewish authorities in Jesus’ day, in occupying the outdated, outmoded, reactive, dying, unsustainable positions.
Jeff, you must be reading Jesus through the lens of some progressive pulpit talker or some other progressive source, maybe even your own intellectual skills. Jesus did not progress on anything. He always went back to the original, to the beginning, to His father who is from the beginning, in whom nothing changes, not even a shadow of it. “On the wrong side of history”, if it means that it is victorious through thousands of years, has nothing to do with anything determinative or authoritative. Sin, in all of it’s gross, wronch reality, has been here since almost the beginning of earth time. The road to destruction is wide and many find that road. It is only the narrow road that few find, that which goes into eternity, beyond history, that has any value for life now. If you are keyed into the “progress of man”, then you will never understand God. He is in need of zero progress.
“…outdated, outmoded, reactive, dying, unsustainable positions.”
This describes homosexuality to a tee. What is new, balanced, living or sustainable about putting sex organs where they are not designed to go? A simple honest question.