posted by gut
I actually think the answer is really simple. He's always grouping them together and attacking them together, and in this case he's simply thinking specifically about Omar.
He should have directed it only at Omar. I think it's a fairly powerful observation to look at her rhetoric, and then point out how she came here as a refugee, and goes on to win a seat in govt making $192k per year. Trump completely fumbled that, practically ruining the argument by including the others, but actually including the others completely distracted everyone from the point.
I get that America was "never great" for a lot of people. But with Omar, her dad even held a govt job working in the post office. So for her to say America isn't great is kind of a GFY moment.
He might have intended it for only Omar, but he never ultimately veered the rest of his point at her, even in a hinting, roundabout way. The whole way through, it was consistent (Congresswomen, countries, places). Even if we assume he was, there is genuine, impartial room to question if he would have done so had one of them been a white man or woman (or whatever other 80 genders there are now).
As for Omar, she's absurd and this little back-and-forth between any of the "Squad" and Trump gives all of them more attention than they warrant.