Bruce Springsteen is a billionaire too, but he's still a champion for the blue collar worker after all these years. His songs are able to hit a nerve with people at a certain socio-economic station.
I am no fan of this woman's music, but I hope that these MAGA folks are not really that dense. Swift's enormous bank account has no relevance to her political endorsements. Her legions of followers and immense popularity are what matters. She is the Elvis, the Michael Jackson, the Beatles of the present.
We don't identify with our celebrities because we connect with their lifestyle. We identify with and love them because they light a spark in our otherwise (often) drab and mundane lives. Again, I don't care for her music, but it speaks to people. I think her songs are quite mediocre, but it's a fool's errand for me to convince my 14 year old that Joni Mitchell's Hejira is much better than any Taylor album.
David Giglio, whoever he is, can post what he likes, but he's a fool to try to explain logically why Swift's endorsement is invalid.