I'm often a Simmons defender, which is probably partly because I line up with his natural demo perfectly - 36 year old white dude from New England that loves sports and pop culture. But he brought a bunch of the most recent **** on himself with the NY Times interview, and the podcast he did with Russillo roughly two Mondays ago.
They usually just do an NBA "redraftable" on a past year lately, but they felt compelled to wade into politics, and it went about as well as you'd expect. During it, Russillo praised Simmons for hiring a diverse group of writers, which got a clapback from the Ringer Union at first, and then got further blowback after that NY Times article. Its hard to say that you just can't find talented podcasters when you're giving shows to 1) your buddy from college and 2) your daughter and 3) of all the people to hire as a producer, you pick your nephew.
I don't know. Simmons has obviously "matured" in some ways - I cringe at times when I read some of his older columns, and I imagine he does too now, since he has a teenage daughter. He's not Adam Carolla, who I also liked in the early 2000s, but who's just gotten more bitter and entitled as he's aged. After that awful Russillo pod two weeks ago, he's had on more diverse guests. I suspect that like a lot of people, he's trying to be better here, but part of that is making missteps and getting called out for it. Hopefully his response to this is to hire more diverse voices, instead of just digging in.