Having suffered net losses; in debt.
Further testimony to his commercial incompetence lay in the fact that, at fifty cents a copy, a complete sellout would have left him worse than $300 in the hole—proof enough, if proof was needed, that it wasn't primarily money he was after; it was fame.
Of a card ("the hole card") which is dealt face down and thus unknown to all but its holder; hence (idiomatic) in reserve; in particular ace in the hole.
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