Growing up in the old West End in the 1950s, Bobby Dellelo mastered stealing cars before he knew how to drive one.
Trouble found him early. He graduated from routine burglaries as a teenager to more sophisticated robberies. During one appalling episode, he and a friend attempted to rob a liquor store in Dorchester. They marched the store’s customers, at gunpoint, into a freezer. As other customers arrived, they put them in the freezer, too. Then they took the money and ran.

Comments
No sympathy for cop killers. And, with lines like this . . . "But the crime that has come to define him involved the murder of a Boston police office in 1963." No sympathy for poor proofreaders. I assume he killed a Boston police officer, not a police office.
Dude..really.. couldn't you find a HERALD this morning? This Article says nothing in sympathy to the killer of a Policer. Dellelo's partner shot the Dectective. Adrian Walker is merely saying that we need to retink the use of Segregation in our Penal System. Again. Stick with the HERALD
Like the songs says "if you can't do the time then don't do the crime.". Perhaps its my age but I have zero sympathy for criminals who complain about conditions in prison, its not there to educate you or tuck you in bed at night, its a place to go after you have broken the laws we all live by. If you can't deal with that then be a productive citizen like the rest of us and realize that life is hard.
Good Column Adrien. Right on Point.
Adrian Walker's article has a hollow ring to it. His compassion would seem more authentic if he expressed it first for Detective George Holmes, then his family and last on the list -Mr Dellelo.
I want to hear the case for Det Holmes and his family after that there may be some compassion left for Bobby Dellelo, otherwise Mr Walker begins to sounds like just another bleeding heart.
What if he didn't rob people and murder them? Just a thought.
Try being in isloation then form an opinion. All the tough on crime advocates have no clue. Part of the reason criminals re-offend is the treatment of prisoners. More then one has opted to shoot it out with the police versus returning to prison, that says something about the conditions which no one understands until they live it. News flash; not all inmates are guilty especially in Mass. where we have the second highest amount of wrongful murder convictions in the U.S., there are innocent people being assaulted and abused in our prisons daily.
This bill stands as much chance as a bill to prohibit hand held devices while driving. Then again, it probably has a better chance.
Some 93 percent of all prisoners will return to society. where we want them to be as peaceful and successful as possible. If being in Solitary confinement for years on end makes them crazier, I agree with Sen. Eldridge's proposed bill to treat criminals as humans who made mistakes, not mistakes who are less-than-human.
Sympathy to the cop and his family for their loss, of course. That's a given, whether Adrian says it or not.
Kudos to Sen. Eldridge for having the courage to speak up for the powerless and disenfranchised in our state.