I love this stuff.
Horse drawn carriages were operated by someone who drove the horses forward, or a “driver.” The advent of automobiles removed the horse but kept the operator, but the term “driver” stuck. (jtgibson describes this better in their reply)
The term pilot historically refers to the person steering/operating a boat rudder. The first (steerable) airships were controlled with a rudder, so the operator is still called a pilot.
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