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What if i'm not able to on my own? ;p Or do you not need to besiege the castle to do that?
Go up to the prison guard, ask him if you can talk to some of the prisoners, he won't allow you, unless you pay him 300 ducats or something. This won't do, even if you pay him, you won't have the keys and can't free anyone; So demand the keys and kill him, enter the prison before the rest of the guards arrive.
Talk to the guy you want to free, and ask him to come with you. Bring along any other imprisoned lords, as they will help you fight during the jailbreak.
If you talk to one of his Lady relatives first, they might offer you a quest to free him. Which will add to the profit of having your lord back.