So Sampo is canon described as the only person who can travel between the overworld and underground, but it's never actually revealed HOW he gets around.
I'd like to believe part of the reason he's so secretive really is just because of business. One of the best ways to keep your customers is by being the only one to offer something, and Sampo stands to make a pretty nice profit if he's the only one able to smuggle in supplies. Gotta protect the trade routes ☆
BUT the other part is because he's probably one of the only ones that could SURVIVE it. I'd like to think a lot of his routes enter the overworld either in places like Backwater Pass, where it's technically in the city but is overrun by Fragmentum, or on the frontlines, where it's frigid cold and crawling with Silvermane Guards.
If someone manages to get all the way up, and even if they manage to sneak past all of the Guards/monsters and not freeze to death, there's still the possibility of getting caught in the city proper by regular civilians.
And if Cocolia heard word of someone caught in the overworld, I can't imagine there's any way she would just leave that, she separated the halves for a reason. This person would be interrogated, and then the route sealed off, and then the Undergrounders would lose a vital supply route. Sampo has to be extremely careful to not get caught and not be tailed.
And I'm sure he does a lot of shady trading in Belobog proper, but I think a lot of it also comes from him looting the Fragmentum-corroded areas, too. After all, in the Cyrille the Fool quest line, when the trailblazer sees something strange in the Fragmentum, the first person they think to consult is Sampo.
So I love the thought of Sampo being like extremely disciplined and being able to be out there for like days at a time.
Looting is easier in the beginning, but eventually Sampo has to go farther and farther out for supplies. Sometimes he'll be out there for days, and it's not exactly a safe place to sleep, but he can stay awake and alert for absurd amounts of time if he needs to be. Going for 24+ hours isn't unusual for him on a big supply run; Sampo will be awake for a day or two, he'll bring back everything he finds to Natasha, then sleep for a solid 8-12 hours and be back up again. He takes a couple of low key days where he rests or does easy work, then he's ready to plunge into the fray again!
On the rare occasions he sleeps in the Fragmentum, it's not for very long, less than an hour, and Sampo has traps he sets all around him while he sleeps sitting up with daggers in hand. Caelus finds out about this habit the hard way because he gets restless and decides to go explore (I'd like to think with the Stellaron dwelling within him, he's largely immune to any kind of Fragmentum corrosion), and he sees Sampo curled up in a corner, head down. So of course he approaches to see if he's ok, and-
A trap pops and hisses
There's a bright flash of pink
Caelus blinks
His back hits the wooden wall behind him
There's the sound of reverberating metal-on-metal right next to his ear
Caelus blinks again
...and is shocked to suddenly find that Sampo is looming over him, pinning him to the wall, one dagger sunk into the wood and the other blocked by his metal bat.
And they both just stand there for a beat, until Sampo blinks the bleariness out of his unfocused eyes, and then he yawns obnoxiously right in Caelus' face and tells him he shouldn't interrupt people's beauty sleep! How is Sampo supposed to stay so handsome otherwise!?
Caelus only notices shortly thereafter that there's a thin line of blood on his neck, and he belatedly realizes that Sampo really would have taken his head off by pure instinct if he weren't also incredibly quick with his reflexes. No wonder he's the only undergrounder surviving out in the Fragmentum; anything that approaches in his sleep thinking they have easy prey is almost instantly demolished.
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I cannot stress enough how much I appreciate JJBA's willingness to explore morally grey characters, especially as the series progresses. At the end of the day, this facet of a character is what keeps me engaged, because you have an (often) deeply flawed person doing their best to achieve their goals, protect the people they care about, and to survive. I genuinely don't think it'd have the same effect if this series was full of Perfect Heroes.
JoJo protagonists (with the exception of Jonathan but I'll discuss that in another post), are messy. Yes they're strong and brave and have a sense of justice but they're also rude, con artists, manipulative, and hurt/kill people as they see fit. And honestly? I love it. I wouldn't have them any other way. It humanizes them. It transforms characters who essentially have superhuman or even godlike abilities and makes them relatable. They struggle with guilt, regret, shame, and anger just like anyone else. They have damaging coping mechanisms. They sometimes take their frustrations out on people who don't deserve it. They're fucked up just like a regular person.
The whole point of this is creating a world where there are no true Good Guys. Everyone's hands are dirty. AND YET, in spite of all of this they still have good hearts. This series could have very easily taken a turn in the other direction and gone the nihilistic route but it doesn't. JoJo could have become a series full of nothing but characters who are only motivated for selfish reasons but it isn't. Not to be cliche, but, at it it's core JoJo is a series about love and friendship and protecting it at any cost. It understands that the connections we have with each other are stronger than any stand. That no matter how fucked up a protagonist or supporting character is they still have the potential to do good. This is a story where, at the end of the day, love will always prevail and I think that's pretty damn wonderful.
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