bail (one) out of jail
To pay for one's release from jail. I have to go bail my brother out of jail again. I wonder what he did this time.
bail someone out of jail
and bail someone out 1. Lit. to deposit a sum of money that allows someone to get out of jail while waiting for a trial. John was in jail. I had to go down to the police station to bail him out. I need some cash to bail out a friend!
2. Fig. to help someone who is having difficulties. When my brother went broke, I had to bail him out with a loan.