Justin nailed it. Its not about who broke it, it's about how the box represents trust within in the group, and after Guarma, all the trust in the group is gone
Metaphor aside, I'm pretty sure it was Karen. From what I've seen she's the only one who really starts acting up around that time, getting drunk often and causing drama. Everybody else is depressed but docile.
It could be anyone, after all a failed bank robbery, Lenny and Hosea's deaths, and being trapped on an island, would be the kind of events that would leave to most people wanting to break something
Whoever did it. They obviously lost faith in the gang and Dutch. Dutch wouldn’t have done it. Micah wouldn’t have done it. Susan didn’t because she found it destroyed. Arthur didn’t obviously. John was in jail. Javier and Bill wouldn’t have. I’d like to imagine a drunk Karen did it.
In my head it was obviously bill you can see him stealing from it so it only make sense he went for what he wanted I’m just I lost 300bucks cause of it.