When using artist’s materials for political purposes, there is nothing about mass production or selling of said artwork involved.
Specifically in regards to political parties/individuals using the visual arts, there are no corresponding performing arts societies or central places where campaigns can go to license large bodies of artwork or photographs. There are websites such as Getty Images and Corbis, where millions of images are available to individually license, but fees need to be paid and restrictions often apply that prohibit or limit political use. The specific license agreement should be read carefully to determine the extent of the license and its limitations. Again, there is no obligation on the part of the copyright holder, that is, the photographer or artist, to grant a candidate or advocacy group the right to use their work. Using work without permission creates the potential for litigation as well as negative publicity.
HBO can go after him for using their licensed designs and materials regardless. And I for one hope they do.