Is there any strong justification for keeping (first-offender) crack dealer in federal prison after 20 years?

The question in the title of this post is prompted by this lengthy new story appearing in the Chicago Tribune, which is headlined "Supporters seek freedom for convict serving life sentence for first-time conviction; Reynolds Wintersmith, 37, has served nearly 20 years on drug offense; his only hope may lie in presidential commutation."  Here is the factual set-up for the question in the title of this post:

Reynolds Wintersmith's first conviction was a costly one.  At 20 he was sent away for life after being convicted in a large-scale drug conspiracy.  It was a mandatory sentence that troubled even the judge, who questioned if lawmakers really intended this kind of outcome for someone so young....

In the nearly two decades since, Wintersmith has been fighting from inside federal prison to convince higher courts of the unfairness of his life sentence — the result of a decision he says he made at 17 to start peddling crack and cocaine after being raised in a family where drug dealing and addiction were part of daily life.

Now, in what seems a quixotic effort, because all his legal appeals have fizzled, a small group of supporters has rallied to his cause. There is his sister, who has stood by him from the beginning. The old friend who dropped back into his life last year and refused to accept that a life sentence was just. A new attorney who was moved to lead the legal fight after taking a phone call about Wintersmith's plight. And just last week, a lawyer who was the White House pardon attorney in the 1990s agreed to consult on the case.

At the time Wintersmith was sentenced, the country was still grappling with how to respond to the crack epidemic. The federal sentencing guidelines were mandatory, giving federal judges no real leeway. Under the guidelines, Wintersmith's crimes were churned through a mathematical formula that spit out a sentence for the judge to impose. A number of factors jacked up his punishment. He was convicted of being part of a Gangster Disciples-run drug conspiracy in Rockford. The law also held him accountable for being a leader in the gang and pushing large quantities of cocaine and crack on the street. The gang also used weapons to protect its drug trade. It all added up to mandatory life, a sentence in which the judge had no say.

For some attorneys and advocates of sentencing reform, Wintersmith's case illustrates the enormous risk behind strict, inflexible sentencing guidelines. They are particularly troubled by his young age and that it marked his first conviction. "There's even more reason to be discretionary in sentencing by not throwing away lives that could be turned around," said Kara Gotsch of the Sentencing Project.

And the federal judge who handed down the sentence lamented at the time that his hands were tied by mandatory sentencing guidelines. "Even though … other members (of the conspiracy) … seem to me to be more significantly involved, and there ought to be some latitude for the court to take that into consideration when you have a 17-year-old who gets involved … there is not another alternative available," U.S. District Judge Philip Reinhard said while sentencing Wintersmith. "It gives me pause to think that that was the intent of Congress, to put somebody away for the rest of their life, but in any event, it's there."

Since then, sentencing guidelines and laws have been changed to temper the stiff penalties in drug cases or give judges more discretion. But the changes came too late for Wintersmith, leaving him with little recourse.... Today, about 2,000 drug defendants — Wintersmith among them — are serving life with no chance of parole, according to the Federal Bureau of Prisons. Love cited a recent recommendation from the American Law Institute, a law-reform group, that calls for a review of lengthy prison sentences — from 15 years to life — to determine if the punishment is still appropriate....

In an interview, Wintersmith, now 37, described a childhood scarred by drugs. Virtually everyone in his family was either using or dealing, he said. He — as well as his sister, Rashonda, in a separate interview — recalled how their mother dragged them into social service agencies, coaching them to "act the fool" so she could get a Ritalin prescription to sell on the street. Wintersmith was 11 and his sister 9 when they woke one morning to find her cold to the touch, dead of a heroin overdose.

They and two younger brothers were then sent to live with their grandmother, but she dealt drugs out of the home, both said. She was arrested when Wintersmith was about 16, leaving him feeling responsible for caring for the three siblings. Under pressure to help pay the electric bill and the rent, he turned to the life he knew — dealing on the street. While he was 17 when he joined the conspiracy, he continued selling drugs for more than a year.

Wintersmith trafficked drugs in Rockford with the Gangster Disciples. The gang had introduced crack — and with it a plague of violence. Wintersmith knows his decisions led him to prison. He has spent almost 20 years understanding why he made them and what influenced him.

Today he has multiple degrees and certifications, earned through the Bureau of Prisons. He counsels suicidal inmates and mentors inmates about to be released — even though he has virtually no prospects for freedom himself. Relaxed as he recounted his story, Wintersmith clearly has spent time reflecting, but he has accepted his lot while still keeping hope for a second chance.

"I still see myself as outside of prison.  This is something I am traveling through.  And I don't want to waste my time. I want to get the things I need to get while I am here," he said of his education efforts in prison....

The best option for Wintersmith at this point would seem to be to petition the White House to commute the life sentence.  The argument would be that justice has already been served and Wintersmith's continued imprisonment would only add to the high cost of incarceration — tabbed at millions of dollars over his lifetime.

I can readily articulate a number of strong justifications for commuting Wintersmith's sentence.  Some are based in changes in the law:  given the SCOTUS rulings in Booker and also the passage of the Fair Sentencing Act, there is every reason to that a 2011 version of Wintersmith would face a much lower sentence than the LWOP term he received two decades ago.  Some are based in equity: given his rough childhood and good works in prison (as well as the constitutional principles articulated by the Supreme Court in cases like Graham and even Ewing), he seems to deserve a second chance at personal freedom despite his criminal activity when a teenager.  Articulated in statutory 3553(a) terms, Wintersmith's two decades in prison already seem sufficient to "reflect the seriousness of the offense" and "provide just punishment for the offense" and "afford adequate deterrence to criminal conduct" and "protect the public from further crimes of the defendant."

Meanwhile, I have a very hard time devising any strong justifications for Wintersmith having to serve perhaps another 40 years or more in federal prison.  Though the principle of "finality" has limited the ability of Wintersmith it get relief in courts based on changes in the law, that principle only provides a justification four courts not revising or revisiting long-ago rulings.  The clemency power in the US Constitution spotlights that the Framers recognized that concerns of finality and the limits of law should not preclude an accountable executive official from prioritizing other values and granting deserved relief or mercy in special situations.  

Perhaps my bleeding heart (not to mention the millions of tax dollars seemingly being wasted on Wintersmith's continued imprisonment) has blinded me to the best arguments for keeping him imprisoned until he dies.  So I hope readers will help me understand any strong justifications for Wintersmith's current fate.  I also hope readers who we especially concerned or moved by Troy Davis's plight will also help me understand why Reynolds Wintersmith's situation is not at least as compelling for national and international concerns as was Davis's.