I think the whole premise is kind of irrelevant. Deathwish has a great team of talented skaters and their image works and their videos consistently deliver.
Baker has a way more iconic legacy and mythos, and Reynolds seems to forgo skill assessments in favor of something else that I don't think even he can put his finger on.
Baker riders tend to become STARS and icons, while Deathwish is a great home for people who are nice and rip on a skateboard.
Andrew Reynolds has an amazing ability to identify not just great skaters, but generation-defining skaters. Think of all the quotes and memes and storied careers that came from Baker 3 alone. And give them the space to shine and bring out the best (and worst) of themselves and each other.
It's not 100% on the money every time (for every Jacopo or Kader, you get Cyril Jackson and Dee Ostrander) but wow it is incredible to see how Reynolds has managed to keep his finger on the pulse for several decades now.
I think that's why he will almost always be respected and borderline revered by the skateboarding community writ large.