His problem was that the image became iconic enough for someone to a.) notice and b.) care. If Dubya’s paintings ever become as iconic as Shepard Fairey’s, someone will probably sue him, too.
The problem is that all art is derivative to some degree. The better you are, the less derivative your artwork is, the harder it is to recognize your influences, and the less likely you are to face a lawsuit or be accused plagiarism. If we decide to let the Associated Press’s legal department decide where to draw the line, then a lot of art simply doesn’t get made because most people aren’t that good, and the subjects that appeal to them aren’t ones that they can render from imagination, or draw from life—and they never get good because we don’t give them permission to suck.