After a jury convicted him last year, former Dynegy executive Jamie Olis was eligible for a relatively light sentence of six months in prison for his part in a natural-gas trading scheme. He wound up getting 24 years - the longest sentence in the history of securities fraud - because the judge was required to take into account the amount of shareholder losses, valued at $100 million.
Now the US Court of Appeals for the Fifth Circuit is considering whether the case should be sent back to Houston for resentencing in light of the recent Supreme Court decision to throw out the guidelines used to calculate Mr. Olis's sentence.
The case is being watched closely by many in the legal community who see it as one of the worst examples of the restrictions placed on federal judges by the now-defunct sentencing guidelines.
Whether the case will be remanded could portend the path of hundreds of other cases on appeal. But even if those cases do make it back to trial courts, how will judges determine appropriate sentences?
Since the high court's ruling in January, the federal court system has been reeling from uncertainty. As trial judges wrestle with how to sentence new cases without the help of guidelines, appellate judges are struggling with how to handle the crush of old cases sentenced with guidelines.
"Judges are still generally following the guidelines with new cases. But figuring out what to do with all the cases that have been sentenced under the old guidelines is the closest thing to chaos you can describe," says Douglas Berman, a law professor and expert on the federal sentencing guidelines at Ohio State University in Columbus. "It's going to take a while for the lower courts to sort through all the issues the Supreme Court has left them with."
Indeed, at least two circuit courts of appeal - in New York and San Francisco - have asked lawyers to hold off on filing appeals until judges can offer some guidance in the coming weeks.
Congress enacted the federal guidelines in 1987 to give judges a sentencing range for particular crimes. Initially, judges could go outside those guidelines for extenuating circumstances, but Congress has continued to cut back on judges' discretion - so much so that the high court finally found, in United States vs. Booker, that the mandatory guidelines violated a defendant's Sixth Amendment right to a fair trial.
The ruling now makes the guidelines advisory. But district judges around the country are questioning what that means as they proceed with new sentencings.
"In light of the Supreme Court's holding, this court must now consider just how 'advisory' the Guidelines are," wrote US District Judge Paul Cassell in a recent opinion involving an armed bank robber. He sentenced the Utah man to 188 months - the exact time called for under the guidelines.
"In all future sentencings, the court will give heavy weight to the Guidelines in determining an appropriate sentence," he wrote. "In the exercise of its discretion, the court will only depart from those Guidelines in unusual cases for clearly identified and persuasive reasons."
In fact, Judge Cassell's sentence is typical of how other judges are responding to the Booker decision. Earlier this month, Judge Ricardo Hinojosa, chairman of the US Sentencing Commission, testified before the House Subcommittee on Crime, Terrorism, and Homeland Security about the impact.
He reported that as of Feb. 4, the Sentencing Commission had received and analyzed sentencing documents in 733
cases since Booker and found that judges had followed the guidelines 90.9 percent of the time. Only 7.8 percent of the cases were sentenced below the guidelines and 1.3 were sentenced above.
"At this point we only have a brief snapshot, but it seems that while judges have been given the discretion to deviate from the sentencing guidelines, they are not doing so in the vast majority of cases," says Kirby Behre, a former federal prosecutor and coauthor of the book "Federal Sentencing for Business Crimes."
While that may indicate to some that judges believe the sentences to be fair, Mr. Behre says it may also be because many of the judges who have come on the bench since 1987 have known no other system. In addition, he says, they have been under constant, sometimes blatant, pressure by Congress to strictly follow the guidelines.
That does not bode well for the hundreds of cases on appeal right now. "It might be a paper victory to have your case remanded, but it's going to be a huge uphill battle to get your sentence changed," says Behre.
Initially, legal experts worried that tens of thousands of cases - all those that have undergone sentencing since Congress enacted the federal guidelines - would be affected by the high court's ruling. But the Booker decision appears to apply only to those cases already on appeal at the time of the Supreme Court's decision.
"A lot of people already in prison had high hopes that their sentences would be reduced after the Booker decision," says Tim Lynch, director of the Cato Institute's Project on Criminal Justice in Washington. "But for the vast majority that is not going to happen."
David Porter, an assistant federal defender in Sacramento, has two such cases on appeal right now. He is hoping to get both remanded for resentencing, but says the difficulty is finding cases that qualify. The easier cases include those in which the trial judge indicated that he or she did not want to give the sentence prescribed under the guidelines, but had no other choice.
That is at the heart of the debate in the Olis case. The government argued in front of the 5th Circuit that Olis will receive the same sentence if his case is remanded, and points to a statement made by US District Judge Sim Lake to back it up: "The court concludes that this sentence is warranted not only by the letter of the sentencing guidelines, but by the need to deter others from committing similar crimes and to assure society that the law will punish those who commit such crimes."
But Olis's lawyer countered that during that same sentencing, Judge Lake lamented that he lacked discretion to give a lighter sentence.
There is no word on when the court of appeals will decide the case.