1. Homophobic. It was dumb, unnecessary and offensive but not nearly as bad as people treated it. It really was just an angry young adult rambling on stream.
2. OWL was super uptight trying to be as "professional" as possible back then. These days, it's much more relaxed. A lot of casters will say "nice" if the number 69 appears on screen and meme on production issues while the players get small monetary fines if they swear on broadcast. One of the main memes of OWL is "sex big dick" having been written in match chat.

That’s also the one that advertised online casino and gambling to his young audience…