The Ringer is not equivalent to an NBA team, and that is where your comparison immediately falls apart.

The NBA is a hugely successful business still on the rise, with so much money involved that it can support a ton of ancillary businesses because of its booming worldwide popularity.

The Ringer is a website trying to start up in a business model every other media company is abandoning. They are trying to make online publishing of written articles a profitable venture, where every other media company has moved away from that as fast as they can. It makes as much sense as starting a new "print only" newspaper does today. It's already a dead end, only Simmons doesn't realize it, won't admit it, or likes hanging out with millennials so much that he's willing to overpay for the privilege.

So The Ringer is nothing like a failing NBA team. It's more like a team in a sport with very limited current interest and with viewership still declining, without any real chance that the public will come back. It will always be niche, not mainstream like the NBA. If the economics of podcasting takes a bad turn, it's probably over for them. CPM for YouTube has fallen off a cliff, so it's not unlikely too.