Recently, I met a man who had spent more than five years in isolation at a prison in the Boston suburb of Walpole, Massachusetts, not far from my home. Bobby Dellelo was, to say the least, no Terry Anderson or John McCain. Brought up in the run-down neighborhoods of Boston’s West End, in the nineteen-forties, he was caught burglarizing a shoe store at the age of ten. At thirteen, he recalls, he was nabbed while robbing a Jordan Marsh department store. (He and his friends learned to hide out in stores at closing time, steal their merchandise, and then break out during the night.) The remainder of his childhood was spent mostly in the state reform school. That was where he learned how to fight, how to hot-wire a car with a piece of foil, how to pick locks, and how to make a zip gun using a snapped-off automobile radio antenna, which, in those days, was just thick enough to barrel a .22-calibre bullet. Released upon turning eighteen, Dellelo returned to stealing. Usually, he stole from office buildings at night. But some of the people he hung out with did stickups, and, together with one of them, he held up a liquor store in Dorchester.
“What a disaster that thing was,” he recalls, laughing. They put the store’s owner and the customers in a walk-in refrigerator at gunpoint, took their wallets, and went to rob the register. But more customers came in. So they robbed them and put them in the refrigerator, too. Then still more customers arrived, the refrigerator got full, and the whole thing turned into a circus. Dellelo and his partner finally escaped. But one of the customers identified him to the police. By the time he was caught, Dellelo had been fingered for robbing the Commander Hotel in Cambridge as well. He served a year for the first conviction and two and a half years for the second.
Three months after his release, in 1963, at the age of twenty, he and a friend tried to rob the Kopelman jewelry store, in downtown Boston. But an alarm went off before they got their hands on anything. They separated and ran. The friend shot and killed an off-duty policeman while trying to escape, then killed himself. Dellelo was convicted of first-degree murder and sentenced to life in prison. He ended up serving forty years. Five years and one month were spent in isolation.
The criteria for the isolation of prisoners vary by state but typically include not only violent infractions but also violation of prison rules or association with gang members. The imposition of long-term isolation—which can be for months or years—is ultimately at the discretion of prison administrators. One former prisoner I spoke to, for example, recalled being put in solitary confinement for petty annoyances like refusing to get out of the shower quickly enough. Bobby Dellelo was put there for escaping.
It was an elaborate scheme. He had a partner, who picked the lock to a supervisor’s office and got hold of the information manual for the microwave-detection system that patrolled a grassy no man’s land between the prison and the road. They studied the manual long enough to learn how to circumvent the system and returned it. On Halloween Sunday, 1993, they had friends stage a fight in the prison yard. With all the guards in the towers looking at the fight through binoculars, the two men tipped a picnic table up against a twelve-foot wall and climbed it like a ladder. Beyond it, they scaled a sixteen-foot fence. To get over the razor wire on top, they used a Z-shaped tool they’d improvised from locker handles. They dropped down into the no man’s land and followed an invisible path that they’d calculated the microwave system would not detect. No alarm sounded. They went over one more fence, walked around a parking lot, picked their way through some woods, and emerged onto a four-lane road. After a short walk to a convenience store, they called a taxi from a telephone booth and rolled away before anyone knew they were gone.
They lasted twenty-four days on the outside. Eventually, somebody ratted them out, and the police captured them on the day before Thanksgiving, at the house of a friend in Cambridge. The prison administration gave Dellelo five years in the Departmental Disciplinary Unit of the Walpole prison, its hundred-and-twenty-four-cell super-maximum segregation unit.
Wearing ankle bracelets, handcuffs, and a belly chain, Dellelo was marched into a thirteen-by-eight-foot off-white cell. A four-inch-thick concrete bed slab jutted out from the wall opposite the door. A smaller slab protruding from a side wall provided a desk. A cylindrical concrete block in the floor served as a seat. On the remaining wall was a toilet and a metal sink. He was given four sheets, four towels, a blanket, a bedroll, a toothbrush, toilet paper, a tall clear plastic cup, a bar of soap, seven white T-shirts, seven pairs of boxer shorts, seven pairs of socks, plastic slippers, a pad of paper, and a ballpoint pen. A speaker with a microphone was mounted on the door. Cells used for solitary confinement are often windowless, but this one had a ribbonlike window that was seven inches wide and five feet tall. The electrically controlled door was solid steel, with a seven-inch-by-twenty-eight-inch aperture and two wickets—little door slots, one at ankle height and one at waist height, for shackling him whenever he was let out and for passing him meal trays.
As in other supermaxes—facilities designed to isolate prisoners from social contact—Dellelo was confined to his cell for at least twenty-three hours a day and permitted out only for a shower or for recreation in an outdoor cage that he estimated to be fifty feet long and five feet wide, known as “the dog kennel.” He could talk to other prisoners through the steel door of his cell, and during recreation if a prisoner was in an adjacent cage. He made a kind of fishing line for passing notes to adjacent cells by unwinding the elastic from his boxer shorts, though it was contraband and would be confiscated. Prisoners could receive mail and as many as ten reading items. They were allowed one phone call the first month and could earn up to four calls and four visits per month if they followed the rules, but there could be no physical contact with anyone, except when guards forcibly restrained them. Some supermaxes even use food as punishment, serving the prisoners nutra-loaf, an unpalatable food brick that contains just enough nutrition for survival. Dellelo was spared this. The rules also permitted him to have a radio after thirty days, and, after sixty days, a thirteen-inch black-and-white television.

