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If he picks her, he must think that he has this election in the bag, as I don't see her helping him particularly with any constituency he doesn't already have.

Guess it depends how badly he thinks his comment about African Americans hurt him with them.

Yes, that is true, and I suppose it is somewhat of an olive branch towards progressives as well.

Whoever he picks for VP will be trying to have a pillow put over his head at night

It is much more likely that they might become president during the four year term, or at least are going to be the nominee for the next election, so it is going to be a pick that's more important than usual.