Fig.: to be in an unfavorable, uncomfortable or difficult situation

Michael's nasty remarks about the office were reported to his boss, and he really ended up behind the eight ball

Il povero Michele si è trovato in una situazione davvero difficile dopo che i suoi perfidi commenti sull'ambiente di lavoro sono stati riferiti al capufficio

My sister wants me to hire his son in my art gallery, but the guy knows nothing about art and he's hopeless. I'm behind the eight ball on this one

Mia sorella vorrebbe che assumessi suo figlio nella mia galleria d'arte, ma il ragazzo non sa assolutamente niente di arte ed è un incapace. Siamo messi proprio male!

This saying comes from the game of 8-ball pool, which is played on a billiard table. In this game, each player is assigned seven balls which have to be all pocketed before the black eight ball. If a player sinks the eight ball before the others, he/she automatically loses the game. That's why, trying to hit a ball that is behind or just too close to the eight ball, is seen as a risky situation.