

I think “plotting” doesn’t see a ton of use in that more neutral sense outside of a few idiomatic cases like “plotting a course”. I definitely did not naturally associate a presidential run with that navigational sense of “plotting”, but instead the “plotting an evil scheme” connotation jumped out. I’d think of planning a presidential run to be more similar in activity to plotting a scheme, another literal plan of actions to achieve a goal, than to plotting a course as a figurative map of those actions. That’s why I interpreted pretty sharply that way, at least.
Let him apply for his own unemployment. Pull himself up by his bootstraps (of other people’s money). Maybe he should even pull the old “as a black man …” while he’s at it and see how it goes there.