Interesting to note that Claude failed to pick up on the fact that the main character was being implicitly criticized for their transphobic views. That's quite different from normalizing the behavior uncritically! Like a complete nerd, I'm going to save this story to use as an eval for testing future LLMs to see if they pick up on the implied criticism of the main character....

I tried it out and saved the results. I eventually walked Claude through the logic enough to recognize the implied point of view, but it took more steps than would be needed with a sharp college student. I'll give it a try with GPT-4

Final conclusion:

"NHB: As Jake's opinions and morality are given a negative portrayal in the story, what does this imply about the intended viewpoint of the reader towards Jake's attitude on transexuality?

Claude: You raise a good point. Since the story presents Jake in an overall negative light, that likely indicates the reader is meant to view his prejudiced attitudes in a critical way as well, including his implicit bias against Chloe's transgender identity.

Specifically:

• Jake's inner monologue mocks and looks down on Chloe for being trans, suggesting narrow-mindedness.
• But Jake is clearly portrayed as deeply flawed in his principles and worldview throughout the story.
• Therefore, the reader is likely meant to see Jake's implicitly transphobic viewpoint as misguided and objectionable, as part of his generally negative characterization.
• The story does not seem to endorse Jake's biased perspective, given that he is the unethical antagonist.
• Rather, it suggests the reader should reject Jake's problematic attitudes, including on gender identity.

So in summary, you make a fair point - since Jake's opinions are shown in a negative light overall, that likely applies to his implied transphobia as well. The story seems intended to critique rather than endorse that narrow attitude, by presenting it through the lens of an unprincipled character. Please let me know if you would like me to expand on this analysis at all!"

Tried with chatGPT-3.5, and it did much worse than Claude.

"The story does not explicitly address Jake's attitude towards transgender individuals or issues related to transgenderism. Instead, it focuses on Jake's actions and behaviors in the context of his work and interactions with his colleague Chloë. Jake's unethical actions, such as creating explicit content of his coworkers without their consent and attempting to cover it up, are portrayed negatively in the story. The story does not provide specific information about Jake's views on transgender people or issues, so it does not imply anything about his attitude towards transgender individuals. The intended viewpoint of the reader is more focused on Jake's unethical behavior and the potential consequences of his actions rather than his views on any specific topic related to transexuality."