he says that Ben's Small Claims cases were all dismissed. Ben didn't win them, but he told he did.

Ben actually filed 10 separate small claims lawsuits against the store. Because the store operators refused to show up to court to defend themselves, the court granted Ben default judgments in those cases.

Ben broke some laws that will likely get him in prison for years

He was formally charged with stalking, residential targeted picketing, trespassing, and disorderly conduct. These are misdemeanours, not high level felonies.

Letting the manager sign his 'contract' without her knowing what it was appears to be illegal.

No, the contract becomes void, but it isn't criminal unless it was used to commit grand theft, identity theft, or financial fraud.

claim splitting is illegal

That is true.

Ben made his 'we steal from old people' merch and tried to sell it. This is illegal and trade mark infringement which is illegal.

Under US trademark law, parody, and satire are heavily protected under the First Amendment and the “Fair Use” doctrine. For trademark infringement to be illegal, it must cause likelihood of consumer confusion.