In the above verse, Jesus is basically defining generosity by examining the effect the gift had on the life of the giver. The gifts of the rich people were meaningless in this sense, because it didn’t affect their lives as much as the gift of the poor widow. In other words, the rich folk could afford to be generous, but the widow could not.
This point is, I think, especially pertinent when thinking through benevolent claims that are made about the generosity of wealthy philanthropists (e.g., the Carnegies, Rockefellers and Vanderbilts of the world). You don’t usually hear about great philanthropists ending up poor. The reason for this, I suspect, is because they give out of their wealth. We need to be honest here, you don’t get rich by being generous, you get rich by being frugal.
This isn’t a secret. It’s been known for a while now that, in the U.S., rich people are not more generous. It seems that when you’re poor, it’s just easier to accept Jesus’ message that generosity is supposed to hurt a little.
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