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I can pinpoint the exact moment: When the admins actively gave t_d a full pass on anything they wanted to do in 2016.
That single act drove away more users than any previous exodus.
There were even earlier signs of Reddit caring more about profit than the best interests of the users.
2014: buying and crippling Alien Blue. Reddit could've built its own official app and users would have two to choose from; or it could have bought and improved Alien Blue. By doing neither, Reddit showed complete disdain towards user experience.
2015: Reddit fired Victoria Taylor. Except that Taylor did an essential job there, as she was a bridge between Reddit Inc. and mod teams; she was for example the one verifying people for Ask me Anything (back then it was a big deal).
You probably could find even more signs of that, if digging further. And while neither is as serious as the way that Reddit handled T_D, both already show that it was putting revenue over users.
There were a few around that same timer period. IIRC, that’s also about when the whole /r/jailbait controversy happened, and the site suddenly had a really bad reputation among non-users. Like before it had been seen as a weird site, but then it was suddenly seen as outright predatory. Users suddenly didn’t want to associate with the site. Then the t_d stuff happened, which just compounded the issue of users not wanting to associate with the site due to the bad reputation.