The problem wasn’t that Contessa wasn’t woke enough, aside from a period of time that Stacy was allied with Zak Smith, and that was several years ago with Stacy since burning her relationship with Zak. There were a couple of problems:
1. It seemed that anyone Stacy associated with she’d eventually turn on in quite public and aggressive ways. Sometimes this may have been warranted, but I can’t recall any associations that survived Stacy’s standard of wokeness. Eventually even GenCon went from being a partner into being a horrible and monstrous place that should be avoided, and also GenCon needs to pay Contessa money for showing up. Any con of significant size is going to have issues. Doesn’t mean those issues can’t be improved upon, but it seemed Stacy’s default mode was set the flamethrower to 10 each time. So going back to the idea that Contessa (and Stacy was the driving force behind Contessa) wasn’t woke enough seems implausible. If anything Stacy’s drive for instant woke utopia now, led her to publicly burning bridges faster than they could be built.
2. Stacy had a vision for how to include women more in gaming that didn’t seem to allow for alternate paths. It seemed like she wanted to set herself up as the ‘Pope-ette’ of women in gaming. She’d criticize in particular efforts by members of the OSR who were taking steps to encourage women in gaming essentially because they weren’t doing it her way. A more productive route may have been for her to say “It’s great that you’re making an effort, even though it’s not how I’d do it. The more trying the better overall.” Instead of viewing games be run for women by male members of the OSR old guard as additional (if different from her approach) avenues to encourage women in gaming she’d trash the efforts. We’re not talking about constructive criticism, which is hard to do anyways on the internet, but essentially demands that these men stop trying to make the effort. It came across to me that she saw these other efforts more as competition than anything else.