Jackson Riles is a racing plane who attempted to become part of the Wings Around the Globe Rally. His racing number is 18.
"Like Dusty, Jackson Riles, was a first-timer at the Lincoln Qualifier. And like every racer, Jackson dreams of racing in the Wings Around the Globe Rally. Powered by a compact air-cooled horizontally opposed flat-four engine, Jackson Riles may not have the horsepower of his unlimited-class competitors, but he has enough passion to make up for the difference."
In Planes, Jackson was seen at the Lincoln Qualifer, attempting to become a competitor in the rally. However, Riles did not make it into the Top 5 to compete after hitting one of the gates.