Wholeheartedly recommend this Slouching Towards Columbia post on the idea of historical teleology.
We must ask what the point even is of being on “the right side of history.” There are different forms of this argument, but all of them are inherently problematic. Inherently, they are teleological, and give history a moral or rational predetermined course. In most cases, these arguments bestow our preferences with inevitability (perhaps with the exception of disillusioned environmentalists such as James Lovelock). We direct these arguments at our leaders and others in positions of power, to compel them to stand with us, on that “right side” which will inexorably wipe out our opponents.
Indeed, the concept of a "right side of history" in itself directs us towards policy decisions that are fundamentally ill-advised. It makes us believe in a linear concept of history in which outcomes are fundamentally pre-ordained. I've always thought that counterfactual history can be of great use to policymakers and analysts. Within realistic parameters of course--"what if black ninjas were present at Gettysburg" is of no use to anyone. But thinking about the way outcomes are fundamentally contingent can be a good source of insight, whether in analysis of military developments or revolutions.
This will also allow me to pimp this thoroughly awesome book again. Best thing on revolutions that Gene Sharp hasn't written.