How the Regime Captured Wikipedia
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I'd say the problem started with Sue Gardener, who was executive director starting in 2007. She's the one who started with the DIE shit by accusing the userbase of misogyny. Jimbo was almost completely absent by that point because he was more interested in finding ways to grift off of Wikipedia's success than seeing through any particular vision. That doesn't excuse his refusal to be the adult in the room when the lunatics took over the asylum but this wasn't his plan from the start. He didn't have a plan and a lot of Wikipedia's dysfunction (which goes far beyond woke infiltration) stems from there being no control at the top in the early days. Their whole "governance" structure consists of gangs of anonymous weirdos fighting turf wars behind the scenes. Jimbo just goes along with the bullshit because he doesn't want the gravy train to end. He's a coward and a grifter but he's not a committed leftist.
He's on twitter retweeting takes from Stephen King about Trump's trial. He may not be the driver of the leftist rot, but I doubt he disagrees with it.
You're really overestimating how principled the dude is. He'd be parroting the shit we say if he thought it would gain him access to the circles he wants to run in and keep the cash flowing. I'm not defending any of the shit he enables, I just think he's opportunist rather than an idealogue.