Okay, Kasumi: A: is not too comfortable leaving Olafsen's pirate crew, which by all accounts is pretty substantial, just lying around with their leader and quite possibly sole voice of conscience, and B: thinks that if Olafsen is serious about walking a more righteous path and finding peace, he gets to start right now.
She proposes that Olafsen give his personal wealth to the citizens of Kargbeck, tell the Imperial Navy where his secret base is, but give his men time to clear out and high-tail it back to whatever country they came from. And he delivers his donation to Holger in person.
When planning treason and revolution, those are two resources it's probably not wise to give up without some degree of consideration, especially since we're considering allying with Olafsen instead of just executing himout of hand.
Especially given that clearing out the base of a fearsome pirate crew is only going to increase the General's political capital and potentially provide him prior access to Olafsen's records before we get to them.
They're not going to listen to us, and they're not going to be happy just sitting on their hands. They're pirates, not a personal navy. We're not going to be able to co-opt them. It's either get rid of them or let them keep raiding local villages.
Do they raid local villages? How many of them, like Olafsen, fell into piracy because it was there?
They will listen to Olafsen. He is a fierce man who inspires loyalty in his followers, and many will probably join him in retirement. And again, it's better for any dissolution of the pirate menace not to be seen to come at the hands of the General but rather the legitimate successor to the throne.
Here's the thing about the pirates. Some of them would probably like to get out of the game, too - maybe they were already thinking of retirement, maybe they agree it's better than getting killed, maybe they were shanghai'd in the first place and were just looking for a way out all this time. However, on the other side, there's a lot of them that won't want to retire. Maybe they're justifiably afraid of what will be done with them for their part in the raids. Maybe having Olafsen come out and betray them will cause them to dig in their heels and fight just for that reason - not to mention how they feel about all the other pirates who would want to give up. There's some who hate the empire or the Hanse and are pirates because it's a convenient way to strike back. And there's undoubtedly some who actually like being pirates and won't want to give that up in any case.
Even if you can convince, say, half of the pirates to give up, you're still talking about two ship's crews worth of pirates who are against you. At best, they'll leave, creating a new splinter pirate faction that's still a threat, more likely you get a fight between the hard cases and those you could convince, and at worst the hard cases are loud enough that most everyone figures it's best to kill you and Olafsen and then carry on.
You're gonna need a little more than speeches here, I think.
Exactly. So, you direct the pirates on raids that are going to mess up the conspiracy's resources. It has the effect of making the conspirators look weak as well as actually weakening them, and the side benefit of whitling down the pirate numbers through simple attrition up to the point where Yukio's people, once she's installed, can ambush the remaining pirates who won't side with the retirees in their HQ
a) identify the conspiracy's resources.
b) convince the pirates that these are good targets.
c) keep convincing the pirates that your plan is sound while they're suffering bad attrition from attacking targets that are too difficult.
Even if they don't suspect that you're deliberately thinning them out, they will think that it's bad leadership to keep losing people on unprofitable raids.
(a) Just as well there's a top flight nosey parker on the team then,
(b) That's Olafsen's job
(c) That assumes they're unprofitable.
Our immediate concern is safely getting to -- and departing -- Olafsen's lair. I don't see any way of doing without Olafsen's cooperation, which means we're either going to make the trip on one of his actual pirate ships, or this imperial ship with its equally untrustworthy crew who, unlike the pirates, probably realise they have a genuine interest in offing the lot of us before that happens.
Doing anything that even looks like ratting out his men before we're wat passes for safely back on home soil might be enough to (a) make him decide to take his chances with the conspirators since he's finally managed to get Yukio where he arguably wants her, or (b) get us in a lot more difficulty than we need to be at this point.
Hmm. The core of the problem, as I see it, is getting them to repeatedly thin their numbers. On the other hand, one spectacularly poor raid could easily do the same job. I think if you can figure out one worthwhile target and make it look easier than it is while arranging for additional opposition, you might be able to get the pirates to break their back on it in either a Pyrrhic victory or a rout. Then you would need another force to come in and mop them up. Oh, and of course in all this you need to convince Olafsen to lead the men who trust him to their deaths.
This also assumes that you're willing to engineer the death of those pirates and whoever they'll kill at the target - probably loyal Imperial citizens or soldiers. Is proper Aiko really thinking in such dastardly ways?
Aiko is an ends can some time justify the means sort of girl.
And the truth of the matter is that by engaging in regime change against a corrupt incumbent is by definition going to get a lot of loyal people killed.
If those loyal people are at least, well, Dirty Dozenish/Section Oneish in that they're all deserving of death and they'll get it dying to further your objectives, then that's a good thing.
