Rockwell did make attempts to make political work towards the latter part of his career. The hard part about being an artist/celebrity of any renown is that your audience becomes sort of like your golden fetters. You can’t change the content of your work less you alienate your fans and more worryingly, your patrons. I admire Rockwell to some degree for taking a chance to address civil rights in some of his works, but theres a lot of reasons why ultimately throse pieces fell short. Rockwell’'s audience at the time didn’t want him to step outside of his folksy genre he had pigeonholed himself into. Its the equivalent to “I just wanted to watch my football and drink my beer man, why you’d have to bring up politics. I get enough of that elsewhere.”

Additionally, in the case of illustration, sometimes your art style just limits the kinds of messages you can say effectively. Rockwell was an illustrator whose style emphasized and romanticized sweet scenes like from a movie. There’s a reason Disney’s artists take so much inspiration from specific artists and illustrators with a certain romantic flair. Take a look at the sickeningly sweet pastel portrayals of the Victorian bourgeoisie from Fragonard, and imagine that style attempting to address political injustices at that time. It just doesn’t work. Not unless you completely overhaul your style and the way you communicate visually can you convey the message effectively.

Rockwell tried to use his talents to address the civil injustices of his time, but due to the preconceptions he had built up over he years around the kinds of messages that work could convey, he ultimately was unable to convey it as effectively as other artists at the time would be able to.

It may not be a fair comparison to make, but the works of Barbara Jones-Hogu were far more effective illustrative pieces that conveyed the sociopolitical sentiments of the time, partially because she was not pinned down by the limitations of what her previous works conveyed.