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Try demolishing your prison, that should release the prisoners
Demolishing the prison worked (dident find a free crime lord in almanac) there really should be option to use shady deal or release crime lord from prison because, you know, you're the el presidente and can do what ever u want.
Could easily be a bug, or could do with the automated arrest mechanic of your police officers. I think they mark criminals for arrest based on the police station efficiency and the criminals proximity to the station. Then it can take months to get a police officer to report for duty and head out on foot to track down the wrong doer