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Being serious, it seems like he picked his people from a couple of pools.
Don’t forget name-recognition (even outside the social media spheres.) When’s the last time so many cabinet picks were names the average American already knew? It’s not like we’re the most informed group of people. Yet out of all the millions of people in the United States, what are the chances that the best people for these jobs are ones the public has already heard of?
Trump has gotten as far as he has by treating his own name like a brand. It’s not surprising that he prefers to associate with others who’ve done the same.