The drug deal that led to Jesse Webster’s arrest was abandoned before it could be carried out, and no cocaine was ever seized to substantiate the kilos attributed to him — enough to compel life in prison. At Webster’s 1996 sentencing, his judge denounced the penalty — “in simple terms, it’s too high” — and conceded the policy that precipitated it was “essentially incorrect.” Nineteen years later, even his former prosecutors agree there’s no justice served by keeping him locked up until his health fails.

Webster was raised on the South Side of Chicago, where his family of seven often went without gas and electricity, supported entirely by his stepfather’s job as a parking lot attendant. Webster found work at a carwash in his early teens, and his unflagging ethic caught the eye of a customer, who offered him a job as a driver. “Where I grew up, drugs was like normal,” he says. “Any concerns I had were outweighed by the needs of my family. OK, I’ll drive you around, but one thing led to another. You get complacent, you get more involved.”

In 1994, when he was 26, Webster helped set up a deal to purchase a significant amount of cocaine from an acquaintance who was cooperating with the DEA. The arrangement was ultimately called off, but a few months later, he heard he was wanted for questioning. “We had a meeting at my mother’s house,” he remembers. “My mom, my stepfather, my brothers and sisters. We decided the best thing would be for me to turn myself in, and then we all drove together. I was handcuffed in front of my family.”

Although Webster wanted to take responsibility for the aborted transaction, the government refused to accept a guilty plea unless he agreed to serve as a confidential informant against a local gang. “They wanted me to wear wires on these guys,” he says. “Obviously I was scared for the safety of my family.” While in custody, he learned that gang members had murdered an informant assisting with the same investigation. Agents offered to put his relatives in witness protection, “but I couldn’t ask them to leave everything they’d known their entire lives so I could avoid a prison sentence,” Webster explains.

He went to trial, but his co-defendants had accepted pleas to testify against him, both about the abandoned deal and about previous drug activity. While Webster was acquitted of actually possessing cocaine, he was convicted of conspiracy to possess the drug, under provisions that extend mandatory penalties for substantive crimes to schemes or attempts to commit them. Because no contraband was confiscated, his co-defendants’ statements — their route to early release — determined how much he’d be held accountable for.

“There is testimony about 12 to 15 kilograms nine or 10 times a year,” Judge James Zagel explained at sentencing, staging simple multiplication to “wind up with” 288 kilos over two plus years. “Granted this pretty much takes the word of…others to establish,” he acknowledged, “and none of the witnesses could be said to have led the existence of choir boys.” Under then-binding sentencing guidelines, he was forced to send Webster away for life, while his co-defendants got off with less than five years each for comparable offenses.

Set by the U.S. Sentencing Commission, the guidelines were ruled advisory by the Supreme Court in 2005, but not retroactively. “How can you say something was broke before,” Webster wonders, “and not fix it for the guys it really affected?” Zagel and both prosecutors involved with his case have written in support of his clemency petition.

To cope with his uncertain future, Webster teaches resume writing to inmates with upcoming release dates, counseling on re-entry even though he’s never supposed to see the outside of his Greenville, Illinois facility. “Giving me a life sentence was saying I was beyond redemption,” he says. “I would like to see somebody succeed.”