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I don't think he could possibly lead a free and unencumbered life even if he's not imprisoned/killed. How many people would sell him a place to live? Food? How pleasant will his life be?
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There are 6 billion people on this planet; I'm sure there are a couple of billion who have never heard of the guy.
How pleasant is Whitey Bolger's life? If it's unpleasant at all, it's only because he's bothered by consistently trying to escape law enforcement. Perhaps a better question would be "how pleasant was White Bulger's life for the decades the Boston Police ignored him"? I obviously don't know the guy, but given his reported lifestyle, the answer is: very. Even when he was a fugitive, he apparently lived a happy life living with friends in Louisiana before he ostensibly left the country.
In case my point isn't clear,
Bulgar was a criminal, murderer, feared gangster, etc. who pretty much ran South Boston for a couple of decades. You can surely Google him up for a list of all the brutal [censored] he did to people for twenty or thirty years. It was absolutely no secret to anyone what he did and what his lifestyle was like, and yet he had no problem running a convenience store where people shopped, finding friends, buying food, socializing, etc. He had a family. A house. He worked on political campaigns. Took vacations. Had millions of dollars. And then the feds finally came after him after a couple of decades, and he disappeared and is apparently living it up with his mistress in Europe. Why is that? Let's try this Socratically.
I understand, you know some ridiculous ACist talking points. That's cute. Maybe you could try thinking critically about this one for a little bit, though. pvn and Boro may or may not have this answer for you, try PMing them I guess.
I suppose half of me isn't intending to be a huge douche, so I'll go ahead and just let the cat out of the bag and answer this for you: the notion that bad people (even ones who commit terrible crimes and horrid acts of inhumanity) won't be able to live a happy life after said acts because "people won't sell them a place to live" or "sell food to them" is hilarious on its face, and is completely contradicted by no less than thousands of contemporary examples, I'm sure. I'm sure you're actually aware of all this, had you thought about it for more than a moment or two. Of course, ACtarding is more fun, so why bother with thinking and such.