in this day and age sneaking something into prison is pretty easy. even with a 3rd generation ipod touch you can jailbreak it and install various hacking tools (command prompt, file browsers and the hacker network known as tor) It is possible Ross might actually be able to hack his way out of prison and escape to freedom. A master hacker like Ross could do it in no time. Prisons are practically automated with all the locks controlled by computers, gards arent even really needed. A team of two to three hackers on the outside armed with camera drones to give ross eyes in the skys could easy project this onto a smuggled google glass that ross could use kind of a HUD from a video game to escape. Im sure ross could do it, if he wants to escape that is. Prison is actually pretty cool, free food, exercise and hanging out with your friends. Im sure he get sa lot of street cred for his hacking skills in the prison, whee most inmates couldnt even successfully install custom firmware on a psp...
You watch too many movies. There are still armed guards watching the towers and patrolling at night. They are ordered to shoot them if they try to escape. Many prisons inmates get no access to computers. I doubt people who had millions of dollars thinks prison is cool. From what I have been told by people who went to prison is that it is incredibly boring. What if you don't make friends but enemies in prison? Life can be very long and harsh.