Since breaking out of jail, even if helped by someone, will most likely fail, after a lot of wasted time, just add a satchel breakout optioon, in which the prisoners get damaged by the explosion, with a massive general breakout. The satchel dude will obviously get MW status, and all the jailed people will be broken out. Also triggering the fire alarm using a molotov and unlocking all the cells would be cool (The cells are togglable like in the story mode, can be opened and closed).
Maybe there should be a cell breakout, instead of a single guy. So if someone manages to open a cell, all the prisoners inside it can escape. This would also give an use to the cell transfer option. Also picking the inmate you wanna be with would be useful.