Both on-deck and in-the-hole were originally naval aircraft carrier terms. In-the-hole is the designated spot where the pilot would wait before going “on the flight deck”. For safety and to avoid confusion this “hole” was below the level of the flight deck. On older carriers, it may have been an actual pit or just a designated off-the-flight-deck spot the pilot would await. So the sequence of a pilot was to be “in-the-hole” until he boarded his plane on the flight deck (“on-deck”). He was then taxied to the catapult where he was launched.*

*http://en.wikipedia.org/wiki/On-deck
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