#1, That's why it's extremely unfortunate that Dale Jr. drove the 88 in the second half of his career. It was simply because he prior drove the "8", but his prior team wouldn't let him keep the number, and he simply doubled-it-up for his second number. Compared with others in that realm of sports, he's rather apolitical, and if I had to guess, I'd say he's probably a moderate.
The connotation with white supremacy/neo-naziism is an extreme annoyance for what is otherwise an innocuous number.