It's one to live with the thought or shame of flipping while in a small town in Montana, quite another when your staring at slabs of concrete in your cell. It's more of a regret feeling. In Casso's situation, flipping or not flipping, he'd still be in prison. I don't think he has interaction with other inmates, which must make him wonder, if he didn't flip and instead went to another USP instead of USP/ADX Florence he'd be less regretful.
"The Feds are a business Anthony, millions of tax dollars are invested in watching your ass, sooner or later, just like you, their gonna want a return on their investment." --- Neil Mink, Tony Soprano's lawyer
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