Having recently compared two lunch companions to each other in point of having checkered pasts, but aware of recent shifts in the meaning of the phrase, and not wishing to give offense, I quizzed one of them on the meaning of 'has a checkered past' as applied to a woman and to a man. He replied that it suggests that the woman was a prostitute and the man a crook. That answer is not wrong and accords with current usage. But the phrase origninally had no such pejorative connotation as far as I can tell. My old Webster's defines checker, vt, as to vary with contrasting elements or situations and gives the example of a checkered career as a racer. Nothing pejorative about that: the racer's career had its ups and downs. Or one might describe a man whose 20s were spent in the Jesuits, his 30s teaching philosophy, his 40s as a soldier of fortune, and his 50's as an exterminator of insects as having had a checkered past. Nothing pejorative about that either.
Only an idiot thinks that change qua change is good. And so I hold to the old way of using 'checkered past.'
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