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While Jumbo is the strongest, he's not the most dangerous.
When you upgrade Crunchy's skill, it shows that there's a second voice and something about him or you not being alone.
I'll be working off of that, but don't know where to go from there yet.
... but someone actually posted the way to get the achievement in the game's discord (and earlier on in a comment under a achievement guide). I used it to get the achievement myself. As the description says, it has something to do with your fists...
You actually have to fight, and beat, all opponent in the boxing ring, and do the prison fluff piece. On the 2nd sunday, you'll be approached by a guard to go to the new route. Be wary : you'll have three (really) tough fights ahead of you without any weapon (but with time between each to use buff items, etc...), I recommend at least a NG+. Then, once it is done, you'll have sit up and escape when opportunity arise, or else you'll be back in the prison. Note that if you didn't obtained the proof at the point, you won't be able to get it before escaping.
Credits where it's due : https://discord.com/channels/924966668017500201/1187090789591945287/1204490002885517433
i did all that and i wasnt approached by any guard on the 2nd sunday . am i missing something?