Like Una, maybe.
Because he has a very specific and explicit concern: is Kirk impulsive enough to start a shooting war.
And yet I remain concerned this brash, young Starfleet captain follows his own rules. I can't help but wonder, is Kirk the reason I was sent here? If I wasn't here to stop him, would we be lead into a war?
There's one, actually, in which Kirk is startlingly smug about Pike's error: "Did it ever occur to you that sometimes you can't avoid a fight? If you had just chased that Romulan ship from the get-go and taken it out, maybe none of this would've happened."
("Did it ever occur to you?" WTF, Pike's got shipmates dying in Sickbay. Kirk's being a callow prick.)
In our culture, your words are a show of weakness.
Just seen as weak, not "as opposed to Kirk." Kirk's not a factor in the Romulan commander's evaluation.
I don't think I can explain it, but... I think I was supposed to meet you...Enterprise would be lucky to have you.
Okay.
This is your original context, which is what I was addressing. Pike does not "know that it has to be Kirk," and certainly there's no strong reason to think that he'd discourage Una from seeking command on the kid's behalf. If they hand off from Pike to Kirk, it's unlikely to be a situation where Kirk is picked ahead of Una by Pike.