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How many who would prove to deserve their freedom should stay locked up to prevent the release of one who would prove undeserving?
Conor Friedersdorf "Why Second Chances for Prisoners Are So Hard to Come By"

That depends. How willing are people to accept a false positive that ends in a serious crime? The answer tends to be: "not very." It's a fairly safe bet that people will be watching Alice Johnson, and if she turns out to commit a serious crime while President Trump is still in office, his campaign's Super Bowl ad featuring her will come back to bite him. A cynical case can be made that this is the very reason why. Ms. Johnson was featured in the ad, and possibly even granted clemency in the first place. Middle-aged women, even those who have few other prospects, rarely go on to become murderers or armed robbers. To a degree, the Trump Administration made a safe choice, and then requests credit for radical reform of the criminal-justice system.

Clemency for prisoners is a form of decision theory that resembles Pascal's wager. If a person is released, and they go on to commit a crime, the public feels the direct harm of that criminal act. But if a person remains incarcerated when they would have avoided recidivism, there is a lot less notice of the unnecessary expense of keeping them behind bars. For many in the public, given that they don't follow the data on the costs of incarceration, keeping people in prison who could be released has no downsides; the money spent on incarceration may as well be a sunk cost, and the human potential has already been written off. In the end, Mr. Friederdorf's question can be considered a corollary to Blackstone's ratio: How many guilty persons should escape, rather than one innocent suffer? Interestingly, according to the Cato Institute(https://www.cato.org/policing-in-america/chapter-4/blackstones-ratio), early core supporters of President Trump said that it's preferable to punish the innocent than to allow the guilty to go free. They were also more likely to support warrentless police stops and other shortcuts of due process.

Generally speaking, I suspect that people are more likely to support protecting innocence over punishing guilty to the degree that they identify with (or fear they may become) the unjustly convicted innocent. Likewise, people who identify with the "deserving" incarcerated are likely to support early release for those who seem harmless than those who don't identify with them. And as there is greater distance between the reformed guilty and the general public than there is between the public and the prosecuted innocent, there is less of a desire to take risks, even small ones, for their sake.

For all that President Trump likes to proclaim that the United States is the best it's ever been, a large part of his message is still about the need to have him protect people from clear and present (not to mention possible) threats. Alice Johnson made a good subject for a commercial specifically because she was non-threatening. Even those people who would use a lapse into recidivism on Ms. Johnson's part as a weapon against President Trump would, I suspect, be surprised to actually see it happen. But for many other people, the idea that if given the chance they'd resort of violence and mayhem is much less of a stretch. And when a society as a whole is risk averse, it's easier to guess which side of the Wager they would come down on.

What would really drive a greater predisposition to seeking out and freeing those who could thrive in society, or at least keep themselves out of further trouble, is need. The public has a certain fear of released criminals going on to commit more criminal acts, and doesn't have any need to see those people as a resource. And so they can eal with their fear by leaving them locked up, and not feel any cost for having done so. Only when there is a need for human capital that has people searching under every stone for more of it will releasing the once-guilty be seen as worth taking a risk for.