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Episode 77, after the attack and the Nein meet with Dairon:

I don’t think Essek did it to gain their trust! I think Essek was legitimately trying to get Caleb killed or stage an incident that might undermine the Dynasty’s willingness to consider a peaceful resolution.

Essek previously permitted unhindered access to the captive Scourger, even with the Bright Queen watching. It was episode 74 that Jester (on Caleb’s behalf) requested a delay for the execution, and then Essek insisted to Caleb in person that they needed to give advance notice to schedule a time to see her again.

While it’s possible that Matt did that for above-table reasons (Mica’s a guest and maybe they didn’t know she was going to join them for more than 1 additional episode), it doesn’t seem especially likely. If they were hard pressed for time toward the end of an episode, Matt could have ended it whenever he needed to and they would pick up in the next.

So for in-game reasons, the cinch of it is why would Essek want the Nein’s trust at this point? They’re a constant security risk for him. Their investigation of the missing beacons carries enormous risk that he would be exposed as the traitor, and he’s been pressed by the Bright Queen to insist that they carry it out. Allowing them to get to know him is practically inviting scrutiny. I think that instead Essek wanted to be rid of them, and when a dragon didn’t eat them, he had an assassination ploy arranged as a backup.

But this is the moment where Essek was standing in ear shot to hear Caleb desperately converse with a Scourger to see if any portion of her regretted what she had done. Essek was there last time and knew that Caleb would speak to her in Zemnian; if he didn’t know Zemnian, it would have been easy to come prepared with Comprehend Languages, either as a scroll or his own cast. Even if Essek hadn’t arranged the shiv (and I still believe he did), he certainly wanted intel at the very least. I expect that he understood the whole conversation.

“Maybe if I could talk plainly with you and see one inch of change, then I wouldn't believe we're all damned.”

I don’t think Essek planned this as a way to gain the Nein’s favor. I think witnessing Caleb’s conversation was the moment that Essek began to have a change of heart. I think Essek believed he was as damned as the Scourger, and he hadn’t believed there was any other option until he heard Caleb say that.

In the aftermath, Essek’s tone of conversation with the Nein is far less abrasive and curt than earlier in the episode. The next time they offer, he agrees to have dinner with them and tells them about himself. Essek invites Caleb to his home. He helps with the spell for Veth.

Let’s play the biggest game of kick the can on the internet.

So may I present my own casting choice for Odysseus:

Absolutely not

You know who would try that shit?

Is this the face of a man who would defy the very gods to get home to his wife?

You know who would defy the gods just to show he could get away with it?

For once I'm not actually doing a bit; those "any resemblance to real persons living or dead" disclaimers genuinely exist because of Rasputin.