Weyoun’s face is everything and Jake is still way over his head
vortaesthetic
This is it. The scene that I fell in love with this sassy little shit.
But if you think about it, he could have been a lot worse to Jake. The fact that he’s still gentle with him despite knowing that Jake is an obvious political dissident suggests that despite their ideological differences, he genuinely likes Jake. Perhaps he identifies with Jake’s youthful optimism, however unrealistic it may be.
In fact, the books take this out even further. In the short story “Three Sides to Every Story” in the anthology Prophecy and Change, Weyoun actively advocates for Jake’s freedom on multiple occasions, going so far as to openly go head to head against Dukat over the way he treats Jake and the Bajorans on the station. Sure, one could say that he’s looking out for a political pawn, but I don’t think it’s anything as sinister as that.
When Jake runs into Weyoun Nine in his cameo in Rising Son, he cheerfully asks Jake about his books. He admits to reading and enjoying Jake’s work, even as his duty required him to suppress it.
ravenamore
There is a scene in the “Millenium” trilogy where Jake says the following to Weyoun::
“Don’t you remember any of the ‘discussions’ you used to have with me on DS9 when you were in control? You never used to care if I didn’t agree with you. You might have clamped down on what I could write, but you never had a problem just listening to me!”
That talk we see in this episode apparently wasn’t the only one Weyoun had with him. It also sort of came off sounding like Weyoun actually liked Jake in a weird, avuncular sort of way, enough that he let Jake vent to him. Could have been part of a long play on Weyoun’s part - converting his enemy’s son to his cause would be a prize - or Weyoun might have kind of admired Jake’s passion.
