Does "Less Blessed" = "Less Fortunate"?

During his speech tonight at the RNC, Senator McCain said that his wife Cindy's "concern for those less blessed than we are ... show [sic] the measure of her humanity."

This reminds me of a phrase I often hear at church and in prayers: the wish that God bless those "less fortunate" than the speaker.

Are these two expressions equal? Are people less fortunate because they are less blessed? Are people less blessed because they're less fortunate?

This is an idea that goes way, way back in U.S. philosophy. In fact, it predates the U.S.A. In a famous sermon given on board the Arbella in 1630 by the British immigrant and Massachusetts Bay Company Governor John Winthrop, the Puritan leader argued essentially that God made some rich and others poor "for the glory of [their] Creator and the common good of the creature, man." It was important that both rich and poor existed, so that "so that the rich and mighty should not eat up the poor, nor the poor and despised rise up against and shake off their yoke."

That is, poor people exist so that rich people can learn to be charitable. Rich people exist to govern the poor people. This causal link between material prosperity and God's favor is, it seems to me, a shaky proposition theologically, but it fits well into the idea of the (U.S.) American Dream and the concept of (U.S.) American exceptionalism.

By Winthrop's logic, and, it seems, Senator McCain's estimation, those who are materially prosperous are so because they are more blessed by God. By the same logic, then, those who suffer more of the many indignities of human life are less blessed.

I reject this equation of wealth and prosperity to blessing. We may receive whatever we have because God loves us. But what we have is not and should never be seen as an indication of God's favor. Such is a perversion of our relationship with our Heavenly Parents, a mean quantification of inscrutable providence and invaluable charity.