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October 1, 2011

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.

October 1, 2011 at 12:05 PM | Permalink


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If if he was in fact part of a gang that used violence to protect its trade then he likely was untroubled by that until he was caught (though he might have been worried that the violence would turn on him rather than protect him, but that's a somewhat different issue). Mr. Wintersmith, has earned the reward of those who give up on society.

Posted by: Soronel Haetir | Oct 1, 2011 1:14:09 PM

sounds like society failed him, Soronel. Did you even read the article?

As explained in the article: As a child, his mom forced him to "act the fool" to get a Ritalin prescription for the mom to sell on the street. When he was 11, the mom died of a heroin overdose. He and his two younger brothers were then sent to live with their grandmother. Guess what? Surprise, she dealt drugs out of the home. The grandma got arrested when he was 16. "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, according to prosecutors."

Now, none of this excuses what he did. But it certainly warrants more than the flippant response you gave.

Posted by: anon | Oct 1, 2011 3:22:17 PM

Was the "mandatory" life sentence a result of a mandatory minimum statute or the then-mandatory guidelines? The article does not clarify that important point. Discussing the harshness and mandatory nature of the guidelines makes it sound like the latter. But if that were the case, why doesn't the Commission's retroactive lower guideline range help him? It makes me think the sentence was due to a statutory MM, which, if that were the case, why go into all the discussion about the guidelines and their calculation?

Posted by: question | Oct 1, 2011 3:35:36 PM

anon: If he had no prior record and he was not responsible for acts of violence I may agree that the sentence was overkill but I strongly disagree with any assertion that "society failed him."

His mother, grandmother, and absentee father set the groundwork for his anti-social acts.

Posted by: mjs | Oct 1, 2011 4:09:04 PM


Posted by: C.A.J. | Oct 1, 2011 4:29:22 PM

There was no applicable mandatory minimum. In fact, the conspiracy count that resulted in a life sentence did not allege ANY specific drug quantities. Therefore, on the face of the indictment, the statutory maximum sentence allowable was 20 years. However, at sentencing back in 1994, the trial judge made drug quantity findings that increased the stat max to life. I know, this seems like a clear Apprendi violation; and you are right. Mr. Wintersmith is no stranger to the Supreme Court, as he asserted (and lost) an Apprendi – esque claim in 1998, two years before the Supreme Court changed course and decided Apprendi. The Court’s opinion in Edwards v. United States is reported at 523 U.S. 511 (1998). You will also recognize Wintesmith’s Sup Ct. case Edwards, as it is the very opinion cited extensively in Booker as being bad law. Easterbrook’s Booker dissent states Edwards (the Wintersmith Sup. Ct. case) was on its “last legs” but the Court must put the final nails in the coffin– and we all know what the Supreme Court in Booker did from there. Bottom line: Wintersmith has repeatedly made claims in court – even the Supreme Court -- that were first rejected, then became non-retroactive law.

Posted by: Strong Ally | Oct 1, 2011 4:36:49 PM

There have been at least three known constitutional violations in Wintersmith's case. Each has been subsequently -- though not retroactively-- recognized by the Supreme Court.

First, the sentencing judge made drug quantity findings that jacked up the statutory maximum sentence that Wintersmith faced beyond that charged by the grand jury in the indictment or for which the jury convicted. The judge's sentencing findings increased the statutory maximum penalty Wintersmith faced from 20 years to life. The Sup. Court in Apprendi held such sentencing-stage findings violate a defendant's Six Amendment right to jury trial.

Second, the sentencing judge in 1994 was required to impose a life sentence under the mandatory guidelines regime. The Supreme Court in Booker struck down the mandatory nature of the guidelines as unconstitutional.

Third, Wintersmith's life sentence is predicated upon nonhomicidal conduct that occurred when he was a juvenile. The Court in Graham held a sentence of life without the possibility of release for a juvenile --who did not commit homicide -- violates the Eighth Amendment's prohibition against cruel and unusual punishment.

Berman, I will answer the inverse of the title question. I believe the most compelling reason for commutation is that executive relief would actually be a recognition -- rather than a rejection -- of the constitutional principles the Court has enunciated since Wintersmith's sentence was imposed nearly 20 years ago. I understand the finality argument; though I believe it is often overused -- perhaps to the point of cliche. If there were just one constitutional violation, maybe we could stand to let that slide as a freebie for the government. Wintersmith's case is different. The sum of constitutional violations, taken together, outweigh any finality argument and render his sentence fundamentally flawed.

Posted by: Strong Ally | Oct 1, 2011 6:15:14 PM

I would actually expect the Graham claim to be a winner, eventually as I expect that to have retroactive application even in federal court. Has he tried raising such a claim? Not that winning a Graham claim would result in immediate release or necessarily even an immediate parole hearing.

Posted by: Soronel Haetir | Oct 1, 2011 7:03:01 PM

I am a musician. Sadly, the sentences for drug offences are passed to correspond with the nation feeling at the time of conviction and this may not realistically express the magnitude of the crime. Selling champagne may have received a harsh sentence during the prohibition era, whereas nowadays no sentence would be applicable.

Posted by: Adwel Lo | Oct 1, 2011 7:08:25 PM

Yes, the Wintersmith case is as compelling, because wrongfully convicted is wrongfully convicted, whether it's 20 years on death row ending in death; or a lifetime in prison, which eventually ends in death. Truly the system is broken, which is why I cannot understand the lack of support for Jim Webb's bill that passed the House and died in the Senate. I'm sure at least some members of Congress didn't know what harm they were doing to human lives when they passed so many inhumane drug laws.
A very personal case in point is my son, a father of 3 who was never in a gang. A gang-banging drug dealer got caught in a sting, and named my son as the person who supplied the drugs he was caught with. He recanted before trial, and was not allowed to testify at trial - instead they used hearsay (which the appellate court found harmless). Because my son had an airtight alibi as to his whereabouts when he was supposed to sell this guy drugs, the jury found him not guilty of that count. But he was found guilty of the count of conspiracy. I have read the 500 page transcript several times, and nowhere was any evidence of a conspiracy mentioned, no co-conspirators, co-defendants, witnesses, physical evidence, surveillance - it was all done in closing statements, and afterwards, the appellate attorney did a motion for new trial, and the judge granted it based on the fact that the government falsified transcripts, used hearsay testimony, and lied to the judge about the missing witness. The appellate court overturned it and he was sentenced to 10 years. This judge also said his hands were tied by the mandatory sentencing, and also said my son did not receive a fair trial and deserves a new one. My son and Wintersmith are only 2 cases, there are many, many more cases of injustice- e.g. Clarence Aaron, Euka Wadlington (google them).

Posted by: msyoung | Oct 1, 2011 9:11:14 PM

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

I am a diabetic. I have done well after 20 years on insulin. Is there any strong justification for keeping me on insulin after 20 years?

Yes. There is. I did terrible before being placed on insulin. I am doing great on it. Why on earth would anyone sane want to mess with that success? The only possible reason would be medical rent seeking, to generate massive medical costs after I stop insulin, go into a coma, and generate huge medical bills. Same with the lawyer and prison.

The prisoner was doing terribly outside. He is doing great inside. He has superior function in the structured setting of the Bureau of Prisons. Releasing him may result in catastrophic relapse into his prior life. Antisocial personality is as permanent and chronic a condition as diabetes. Insulin is a miracle drug. In this case, prison was a miracle life saver. Anyone will releasing him will be fully responsible for the foreseeable, catastrophic consequences to him and to his surroundings. Given this certainty, the person releasing him should be sued by both the prisoners and his crime victims.

Posted by: Supremacy Claus | Oct 1, 2011 9:22:26 PM

Miss Young: Is your son black?

Posted by: Supremacy Claus | Oct 1, 2011 9:25:30 PM

Miss Young: Is your son black?

Yes. Why?

Posted by: msyoung | Oct 1, 2011 9:43:48 PM

Race explains his torments, and unfair treatment.

Posted by: Supremacy Claus | Oct 1, 2011 10:30:36 PM

We discussed the treatment of black people by the feminist lawyer running the law today.

It took the KKK 100 years to lynch 5000 extra-judicial murder victims. They did so publicly, sent post cards of the scene to friends as if at the beach. You may have been taught the lawyer lie that they hanged black kids whistling at white trash women. Not so. They lynched rich balck people and took their assets, including their expensive homes.

Today, feminism has replaced the Klan. The black family survived kidnapping, slavery, war, poverty, discrimination. It did not survive the assault of the feminist lawyer, and today 70% of black kids are bastards. That is not an accident. Please, review the definition of child abuse. It describes the child rearing of Southern culture that produces very mannerly young women and men.

And the number of excess murder of black people, especially productive black males, is 5000 a year. We reviewed that blacks are 10% of the population, and should have 1700 murders, instead they have 7000 murders a year, with an excess of 5000, for the past 50 years. That means 250,000 black males were murdered that should not have if the murder rate were truly randomly distributed. The feminist is 100 more lethal than the Klan.

Black men are targeted by the feminist at every step of the judicial system, from the police not providing protection as they pledged to, to arbitrary, lawless appellate decisions as in the case of your son. These feminist lawyers are on a all out war against our people to generate lawyer fees. Your son was a commodity traded and sent around like corn or beef.

Whites should not feel smug or safe. The feminist lawyer is coming after the white family as well.

Posted by: Supremacy Claus | Oct 1, 2011 10:45:49 PM

So let's say President Obama commutes this guy's sentence. Who gets the blame if this guy reoffends?

Posted by: federalist | Oct 2, 2011 9:48:44 AM


Society, of course. Don't you know that it's never the offender's fault? Always somebody else is to blame.

Posted by: Soronel Haetir | Oct 2, 2011 11:42:44 AM

federalist and Soronel --

You're a mite optimistic in thinking the press would ever let the story of a re-offense see the light of day.

Posted by: Bill Otis | Oct 2, 2011 2:30:03 PM

What if he re-offends? What happened to the idea of rehabilitation? He made these decisions when he was 20 years old. He now has multiple degrees and he counsels others in the institution he's in. I agree with Supremacy Claus that Black men are targeted, however, I don't think it's the feminist lawyer alone. The feminist lawyers, just like the smug white men, are representative of a corrupt and broken system of injustice, where prosecutors are rewarded for convictions, by any means necessary. Where non-violent offenders are given life sentences, while violent criminals are given years and let out to commit more crimes. But just for argument's sake, are there any statistics that say that men or women who get involved in drug traffiking at a very young age remain criminals all of their life. And, if this stupid war on drugs (i.e., war on Blacks) should ever end, what would they have to re-offend against?

Posted by: msyoung | Oct 2, 2011 9:47:54 PM

What if he never re-offends? What if he re-offends because after 20 years in prison he's incapable of coping with the pressures of life outside prison? What if he re-offends by driving over the speed limit? What if he re-offends by moving to California, getting a medical marijuana card, and smoking marijuana? What if he never re-offends, but is falsely accused of re-offending? What if he re-offends by agreeing with someone to smuggle drugs, but no one ever actually smuggles any drugs and no one finds out about it? What if he would have discovered a cure for cancer if he'd never been locked up? What if he lives a quiet life and is never heard from again? What if he dies from a horrible traffic accident? What if he has kids and they commit heinous crimes?

Posted by: C.E. | Oct 3, 2011 2:11:49 AM


Re-offense is a risk in every case where there is a non-terminal sentence. If release were only justified in cases with a verified 0% chance of reoffending, all felony sentences would be LWOP (if not death). Even under the common law, this was not true in practice (although death was for a time the only penalty on the books). In other words, you are not saying anything that can't be said in *every* case. (And most cases do not exhibit the evidence of rehabilitation present here.)

Granted, the original sentence here was LWOP. But there is abundant reason to think that sentence is flawed and was reached through procedures and rules that are now thought to be unfair and inappropriate, though unreachable through legal appeals. Seems like a classic case for executive clemency. There may be arguments against that, but the mere, always-present *possibility* that he could re-offend is not a good one, especially in the face of substantial evidence that he has reformed and sought to better himself in prison and is thus *less* likely to reoffend than most.

Posted by: Anon | Oct 3, 2011 11:55:49 AM

Posted by: Anon | Oct 3, 2011 11:55:49 AM

I have advocated numerous times on this forum that between 75 and 90% of felons should be executed, so your solution doesn't particularly bother me.

Posted by: Soronel Haetir | Oct 3, 2011 1:13:30 PM

'75 and 90% of felons should be executed'

I'd have to agree with that sentiment and those percentages if it also included the jackasses that make statements like that.

Posted by: General comment | Oct 3, 2011 6:50:45 PM

"Wintersmith's life sentence is predicated upon nonhomicidal conduct that occurred when he was a juvenile. The Court in Graham held a sentence of life without the possibility of release for a juvenile --who did not commit homicide -- violates the Eighth Amendment's prohibition against cruel and unusual punishment."

This is a particularly compelling reason, since it is essentially substantive and not procedural and is squarely applicable in this case.

Posted by: ohwilleke | Oct 3, 2011 7:18:17 PM

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