so at 65, anthony peppe is an anomaly. >> the system does not discriminate from young to old or middlens. if you do something bad in boston, you're coming to here or maybe you're going to state prison. >> he's an old-timer. he's a hardened criminal, been in and out of institutions his whole life. he's one of those guys, he doesn't really bother anybody. he does his time, knows how to do time. >> peppe is currently serving a two-year sentence for the unauthorized use of a motor vehicle and possession of a firearm. >> i call him the don because of the way he walks around and he walks around like he owns the unit or thinks he owns the unit. >> part of peppe's swagger is due in part to his skill at gaming strategy. in jail, the stakes can be for canteen, phone calls, or something more creative. for william allen, losing means sweating. >> you're down 77 pushups so far what would you like to play for? >> another 20. >> okay. your first move. >> we play for pushups on demand. i can call for these pushups at any time of the day or night, no matter where he is on this unit or if we're in the y