The password is 'jailbreak'.
For a jailbreak to be done right you will need to be very thorough.
C4 comes to mind
High Trust, Low Trust, No Trust
Then - degringolade.
The trust that used to bind us together didn't fail due to its internals - it was pushed down the stairs by those seekign to collapse our once free Republic and replace it with... something else. Solzhenitsyn wept.
The password is 'jailbreak'." - The Comedian
Jailbreaks are too difficult to pull off successfully... Someone or something always gets messed up. Work smarter, not harder...
To that end: Forget trying to bust him out of a structure, bust him out of a vehicle. He has to be transported outside of prison walls for a trial or appeal, right? Block in transport vehicle, yank an innocent bystander (not really innocent - bystander is actually part of team and in on the plan) up as a hostage and hold gun to their head telling guards hostage will be shot if they don't release the prisoner. With this plan executed on a side street (used by prison transport to avoid perceived threat from heavy traffic) there is less chance of getting caught, better chance of blending in with other traffic, especially if you drop primary vehicle for secondary vehicle once out of view (may involve entering a parking garage in order to get out of view of an observing aircraft, but effective). Have all required "new identity" documentation, anonymous Tracphone, along with check/carry-on luggage ready to get subject out of the country and drive him to straight to the nearest airport (tickets paid for with prepaid debit card in an untrackable name.) Send subject support money in new country via established PayPal accounts by purchasing (non-existant) items from him on eBay. The subject needs to be out of the country, or at least on an outbound flight, within 1-2 hours in order to stay ahead of the BOLO.
See what happens when I can't sleep at night? And this plan just scratches the surface. ;-)
Regards,
Raven6