Imagine a corporate executive named John Doe who's worth about $100 billion and ranks as one of the tree most famous people in the world. I want to write a tell-all book about him, focusing on corruption. I'm going to make the case that he's a cutthroat businessman who knows how to bribe people and manipulate the law.
My book is titled "John Doe 101." The front cover features a photo of John Doe. (The photo is public domain.) The book features several pictures of John Doe, including photos and caricatures.
I also make a companion poster titled "John Does's Tips for Getting Rich by Cheating People." It features a caricature of John Doe above a list of ten tips and sells for $5.
I then make a flyer advertising the book and poster. The flyer features a picture of John Doe.
Could any of the above be characterized as unlawful commercial appropriation of likeness?
My guess is that everything I've described is perfectly legal except perhaps the poster.