Meaning: an impossible 'no-win' situation
Originally exclusive to bureaucracy, and used to describe a regulation which depended on another, which in turn depended on the first, this idiom today is used to describe any no-win situation, or a situation which seems impossible or difficult because it contains two opposite facts. It originated from Joseph Heller’s famous 1961 novel of the same name.
'He couldn't get a job because he was homeless and he couldn't get a house because he didn't have a job. That's a real Catch 22'!