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The current wording of the passage "Match objects always have a boolean value of True" implies that the value compares equal to the ‘True’ constant. That implication is incorrect.
I disagree with R. David Murray; if we want to say that a value is considered true *in a boolean context*, that's very different from saying it has the "True" value.
Georg, "evaluates true in a boolean context" has the meaning you're seeking; it is chosen precisely because it does *not* imply equality to the True constant.