Historical Lord Timothy Dexter - America's First Lolcow who constantly failed up and felted his alogs. The original teflon tard.

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Nice thread, Dexter is definitely a historic lolcow.
I'd say he goes beyond a lolcow. He could've been a fucking Looney Tunes character with how he always seemed to get the best of his A-Logs. If he had a thread today, most of the posts would be about people seething about him.
Everything I'm reading about him makes him sound awesome.
I can't tell if he was just an elaborate troll or what the story was exactly.
He wasn't a troll but he also wasn't as stupid as people thought he was. The example of him selling cats in the OP came as a result of his town being overrun with feral cats and nobody knew what to do with them. So he graciously volunteered to get rid of them by loading them all up on his ships and selling them to the plantations he did business with. That would be an impressive business move for someone who wasn't a famously illiterate moron.
 
The one unanswered question I have is WTF is going on with the cats in the red square:

cats.png

These look like @Cats type cats. The one further back has a head that narrows to a point skyward so it is apparently a conehead cat. The one in the middle has what appears to be a bobtail where it's head should be, so truly ass backwards. The one furthest forward is literally a headless cat. So, he was trading in derpy cats apparently.
 
The one unanswered question I have is WTF is going on with the cats in the red square:

View attachment 6937041

These look like @Cats type cats. The one further back has a head that narrows to a point skyward so it is apparently a conehead cat. The one in the middle has what appears to be a bobtail where it's head should be, so truly ass backwards. The one furthest forward is literally a headless cat. So, he was trading in derpy cats apparently.
they're AI images - OP says it
 
they're AI images - OP says it

Yes... I know... the point of my post was to shitpost about the AI rendering derpy cats. Essentially shitposting the shitpost. Shitpost inception. Apparently I was too subtle in my analysis. I'll have to be less convincing next time that I was making an effortpost rather than a shitpost.
 
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