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I wouldn't call that wishcasting as much as the "well Mr. X went to the same school I went to so obv he's probably pretty smart QED" part.
Giving DS benefit of the doubt, I think his argument was that Trump had to take a course in it (which DS knows by the fact that Trump went to Wharton), whereas Maddow did not.
Still, I have a hard time imagining that Trump understands this, or much of anything beyond the level of a 12-year-old. Being required to take a course in something 40 years ago != understanding what was taught in that course.