In this article in the Weekly Standard about the situation involving Michael Vick, the NFL quarterback who was just released from a sentence for running a dog-fighting club, the question is posed, “When is a crime paid for?”, which is an excellent question in the arena of criminal reformation.
The best answer, I believe, in this era of total access to criminal records, is that for reentering penitential criminals with extensive criminal involvement (which doesn't apply in Mr. Vick's case)—regardless of the crimes—is probably never; and for the penitential criminal the best response is to assume the rest of your life should be committed to helping the society you harmed during your criminal life, and you should expect nothing in return for that help.
It is very reasonable for most people to always remain suspicious and wary of someone with an extensive criminal past, and for the reformed criminal to not accept this is not really on point with what his internal and external work should be about, coming closer to God.
An excerpt from the article.
“It was Vick's lack of "remorse" that led the judge in his case to slap him with a longer sentence than his fellow defendants. But one cannot measure remorse. (One can measure servility, which is perhaps what those who call for remorse are generally seeking to procure.) And why should we care about remorse? We don't need Vick to love dogs. We just need him not to repeat his crime.
“One of the great things about incarceration is that it relieves us of the need to look into our fellow citizens' hearts. "He's done the time," said Terrell Owens of the Buffalo Bills. He is right. We need to revive the idea of "paying one's debt to society."
“Other-wise we blacklist people forever, which is to say, we establish "debts to society" incapable of being paid back.”