1993, Shelby Foote, introduction to Stephen Crane, The Red Badge of Courage, The Modern Library (1993), →ISBN, unnumbered pages:
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.
Instead it was a critical and commercial bomb that put his production company millions in the hole, necessitating two Pusher sequels (in 2004 and 2005) to get him in the black.
(stud poker) 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.