I listened to the recording, and read the transcript, and I can... I can see it. Not overtly, not intentionally - but the dev did not communicate clearly at all.

Twice the Reddit representative asking him to repeat himself, and still he failed to actually specify his intentions. The wording in the transcript never actually expanded what the dev was saying ('buy out Apollo'). The evasive language made it sound like a shakedown, 'pay me $10mil to make this all go away'.

I linked the dev's own transcript above, but the actual quotes from the dev:

I could make it really easy on you, if you think Apollo is costing you $20 million per year, cut me a check for $10 million and we can both skip off into the sunset. Six months of use. We're good. [Low voice:] That's mostly a joke.

Okay, if Apollo's opportunity cost currently is $20 million dollars. At the 7 billion requests and API volume. If that's your yearly opportunity cost for Apollo, cut that in half, say for 6 months. Bob's your uncle.

I was just saying if the opportunity cost of Apollo is currently $20 million a year. And that's a yearly, apparently ongoing cost to you folks. If you want to rip that band-aid off once. And have Apollo quiet down, you know, six months. Beautiful deal. Again this is mostly a joke, I'm just saying if the opportunity cost is that high, and if that is something that could make it easier on you guys, that could happen too. As is, it's quite difficult.

Now, we know that what the dev is doing is essentially offering to outright sell Apollo to end the demand it represents to Reddit. He doesn't expect them to take it, but a lot of users asked if it were possible, and he's suggesting it anyway.

But the wording of all of this never specifies 'buying Apollo'. It sounds like he wants Reddit to like... pay him his 'protection fee'. I'm sure he means 'go quiet' as in like, 'go quietly into that good night' (shut down) or 'stop being so demanding' (be retooled), in fact he later clarifies he means the latter and the Reddit representative apologises profusely.

But man, that was worded so poorly, and he was given two opportunities to clarify, and he just... didn't. Only when the Reddit stand-in asked if he was suggesting Reddit buy his silence and compliance did he clarify that wasn't at all what he was saying.

It was completely unintentional, no doubt. But it was miscommunication of the highest order, and it damaged the lines of communication so irrevocably it probably incentivised Reddit to cease negotiations completely.