Rocky was not without experience. He had personally commanded the fights against Baron Wolin and the Wild Horse Air Pirate Group, and these battles had allowed him to amass quite a bit of experience. Thus, he had immediately adjusted his formation after the first battle to prepare for an even larger conflict—a decision that clearly stemmed from experiential judgment.
However, his experience, while perhaps rich compared to some, paled in comparison to that of Madison, a veteran of many battles. This gap led to Rocky's relatively superficial understanding of aerial combat, his immature grasp of the situation, and incorrect judgments on the spot.
Take the present situation, for instance.