The Supreme Court takes another crack at sorting out the sentencing rules.

Oral argument from the court.
Oct. 2 2007 6:38 PM

Run-On Sentencing

The Supreme Court takes another crack at the sentencing mess.

At the risk of an unfair generalization, I think the legal world sorts rather neatly into Booker people and non-Booker people. One of my best friends is a Booker person. Can talk about sentencing cases for hours. Days. The wonderful Doug Berman is the Booker czar and his blog is the Booker holy grail. Me? Not so Booker.

The oddities of the high court's strange bedfellows and the weird twists and turns in its Sixth Amendment jurisprudence are endlessly fascinating to Booker folkprecisely because they defy all expectations and easy categorization. The world's non-Booker people evidently include an old college friend, now an attorney, whom I nearly mow down on the Supreme Court's plaza after argument today. "How do you think it went?" I ask him, eager for some insight. He rolls his eyes. "Booker," he sighs.

Dahlia Lithwick Dahlia Lithwick

Dahlia Lithwick writes about the courts and the law for Slate. Follow her on Twitter.

In 2005, the court held in United States v. Bookerthat the federal sentencing guidelines, formerly mandatory, were now "advisory." In case you think the justices were clear on that matter, let me just point out that John Paul Stevens delivered part of that opinion, joined by Antonin Scalia, David Souter, Clarence Thomas, and Ruth Bader Ginsburg, while Stephen Breyer delivered another part, joined by Chief Justice William Rehnquist, Sandra Day O'Connor, Anthony Kennedy, and Ginsburg. Stevens, however, dissented in part, and Souter joined, as did Scalia (except for Part III and Footnote 17). That doesn't account for all the dissents. This stuff is Christmas in July for the Booker people.

The obvious problem after Booker is that if the guidelines are less guidelines than "hearty suggestions," how precisely do you apply them? Both of today's arguments deal with this lingering question: How do you make advisory guidelines mandatory, while still ensuring that they are advisory? And how do you communicate all that to the sentencing judges, who are deeply confused about where the line between mandatory and discretionary sentencing now lies?

In the first case, Gall v. United States, the court must deal with a federal judge who decreased the guidelines sentence of 30-37 months' jail time for Brian Gall to three years' probation. Gall, who briefly sold a whole lot of ecstasy in college, impressed the judge with the fact that he voluntarily withdrew from the conspiracy, focused on college, started his own business, and was only 21 at the time of his offense. The 8th Circuit Court of Appeals was appalled at what it saw as a "100% downward variance" from the guidelines range to no prison time, and it slapped the district court for departing from the guidelines in a way it deemed disproportionate to the seriousness of the offense.

The second case involves a similar downward departure for Derrick Kimbrough, given 15 years for dealing in cocaine instead of the guideline minimum of 19. The judge based his leniency on, among other factors, Kimbrough's military service and the sheer dopiness of the so-called 100-to-1 powder-to-crack ratio in the sentencing guidelines. (If you are convicted of selling 5 grams of crack, you get the same five-year mandatory prison sentence as the dealer who sells 500 grams of powder cocaine.) As Harlan Protass explains, that 100-to-1 ratio is a dumb relic that has gone unfixed in Congress for years. The 4th Circuit, in reversing Kimbrough, spanked the judges who take it upon themselves to ignore the 100-to-1 ratio in sentencing. The appeals court found that sentences outside the guidelines range would be "per se unreasonable" if based on a judge's policy disagreement with the crack/powder disparity.

So today we have the court beating away at one side or the other with the same line of questions: Are the guidelines mandatory or not after Booker? If they are not mandatory, how do we curb runaway judges? If judges can depart from the guidelines, how much is too much, and who gets to measure? If they can't depart, the guidelines are mandatory, aren't they?

One of the first big concepts they teach at law school is the distinction between rules and standards. If you are worried about too much open-ended discretion and variability in the law, you'd prefer a system of rules: The sentencing guidelines ensured that similar crimes led to similar times. If cold, impersonal rules that aren't tailored to the nuanced facts of the case make you nervous, you tend to favor open-ended standards: If statutory sentences are too tough, judges should be able to ratchet them down under the right circumstances.

But how do you enforce a squishy standard? And how do you build discretion into a rigid rule? It's like a snake swallowing its own tail or a maze that inevitably leads back to the beginning. Jeffrey T. Green, arguing on behalf of Gall, tells the court that appeals courts may look at a broad range of cases to determine whether a downward departure is out of whack. "But what's the point of looking at a broad range of cases if the appeals courts can't do anything about it?" asks Roberts.

Breyer asks: "What words should be written that would lead to considerable discretion but not total discretion, so the goal of uniformity is not totally destroyed?" 

Roberts asks what's wrong with saying that sentences that are out of the norm need to be grounded in good reasons. "Because it sets a presumptive sentence that is the guidelines sentence," says Green. "It tells the district court you're taking a risk for going outside of the guidelines."

After beating up on Green because standards are not rules, the court takes aim at Deputy Solicitor General Michael Dreeben, because, well, rules are not standards.

Scalia asks how Dreeben can concede that the guidelines are advisory, yet make them "pretty much mandatory." He adds: "You are just blowing smoke when you say the guidelines are advisory. Your criterion for fairness is the guidelines!" Stevens adds: "You're saying a sentence is not unreasonable if it's outside the guidelines, but it's unreasonable if it's dramatically outside. You just can't tell me what 'dramatically' is."

Things get even murkier in Kimbrough, where Dreeben takes the position that there is something magical about the 100-to-1 crack/powder disparity that makes it even less advisory than the rest of the advisory guidelines. Stevens hammers away like Dreeben is Mr. Spock from Star Trek, begging him to offer some formula for downward departures that isn't cold and mathematical. Breyer almost weeps for the dying guidelines.

Scalia concludes that "it may be impossible to achieve uniformity in guidelines that are advisory … which is why Congress made them mandatory." Later he says, "We're trying to develop a rule that can be applied sensibly. ... You haven't given us a rule. … If I were a Court of Appeals judge, I would have no idea when I could [depart down from the guidelines] or when I could not."

So just to catch you non-Booker people up on what you've missed in the last few years: There used to be a lack of uniformity in sentencing. Congress created sentencing guidelines. The court decided the guidelines were merely advisory. Appeals courts said sometimes advisory guidelines are still mandatory. District courts got confused. And now the high court asks the parties to make immutable rules out of standards, and flexible standards out of rules. Kimbrough and Gall think a good rule is that the guidelines should go away. The Justice Department thinks a good rule is that the judges should go away. And the court? It may finally have to pick a side.