But perhaps his fortunes have turned again. The Supreme Court plucked his petition from the thousands that make their way to the court each year. This month, Pepper won his case in a victory that gives federal judges more leeway to provide second chances to the criminals who come before them.
The ruling will clarify the rules that guide judges as they try to set sentences that both comport with national norms and ensure justice is done in individual cases.
But Pepper v. United States also is a reminder of the real people behind the court’s cases. It comes with a story that might make even the most objective balls-and-strikes umpire on the mahogany bench feel a tinge of (can it be said?) empathy.
Justice Sonia Sotomayor, who wrote the court’s 7 to 1 decision, summed up the parameters of Pepper’s journey through the halls of justice pretty well.
“At the time of his initial sentencing in 2004, Pepper was a 25-year-old drug addict who was unemployed, estranged from his family and had recently sold drugs as part of a methamphetamine conspiracy,” Sotomayor wrote. “By the time of his second resentencing in 2009, Pepper had been drug-free for nearly five years, had attended college and achieved high grades, was a top employee at his job slated for a promotion, had re-established a relationship with his father, and was married and supporting his wife’s daughter.”
Nevertheless, the U.S. Court of Appeals for the 8th Circuit said that his original sentence had been too light and that, under federal sentencing rules, the remarkable changes Pepper had made in his life could not be considered at his resentencing. A different judge gave him three more years and sent him back to prison.
“It was crushing,” Pepper said in a telephone interview last week. “Honestly, I felt like my life might be over. I know that might sound overly melodramatic, but at the time, just to know that I had been out for four years and all of a sudden I’m going to have to go back and leave my family, and for what?”
Pepper, who lives in Sioux City, Iowa, acknowledges that he caught a break at his original sentencing; the plea agreement he reached with the government made him eligible for 10 years in prison. But District Judge Mark W. Bennett took note of his cooperation with authorities and sentenced Pepper to two years in prison and five years of supervised release — a sentence that was 75 percent below the lightest the guidelines recommended.
Pepper said he understands why the government appealed. “Judge Bennett gave me a break. I understand that,” he said. “But I do think I took full advantage of that break. I tried to show him and the government that the judge didn’t make a mistake by giving me that light sentence.”
He had just been released from supervision when the appeals court said he would have to be resentenced. He’d been named associate of the year by Sam’s Club when another judge ordered a new sentence of 65 months and sent him back to prison.
Sotomayor acknowledged that federal sentencing guidelines did not allow judges at resentencing to consider factors not considered at the original sentencing. The guidelines obviously would make Pepper’s rehabilitation off-limits.
But she said that restriction did not survive the court’s 2004 decision that the sentencing guidelines be advisory rather than mandatory. More important, she said, was that judges consider all available evidence to determine what punishment is best.
Chief Justice John G. Roberts Jr. and Justices Antonin Scalia, Anthony M. Kennedy and Ruth Bader Ginsburg agreed with Sotomayor’s opinion. Justices Stephen G. Breyer and Samuel A. Alito Jr. agreed with the outcome, but both worried that Sotomayor’s broad ruling was a further watering-down of guidelines meant to make sure sentences are uniform. Justice Elena Kagan did not take part in the case.
Only Justice Clarence Thomas voted against Pepper, saying he was “bound” by the federal rules. But he added, “In light of Pepper’s success in escaping drug addiction and becoming a productive member of society, I do not see what purpose further incarceration would serve.”
So Pepper waits to be sentenced again. Life is not quite as serene as it once was. His marriage has fallen apart. He is about to start a new job.
But Pepper was “ecstatic” when he got the call from his lawyers about the decision. “It was like I’d been waiting for that phone call for years,” he said. “I can’t imagine you can win a Supreme Court case and not have it affect your resentencing.”
But in the worst case, he said, he had only eight months left on his term when the Supreme Court intervened. If he had to, he said, he could do that.