Mitchell: Jesse Webster — from prison to redemption

SHARE Mitchell: Jesse Webster — from prison to redemption

Jesse Webster, whose prison sentence to life without parole for a nonviolent drug offense was commuted by President Barack Obama. | Ashlee Rezin / Sun-Times

Follow @MaryMitchellCSTEDITOR’S NOTE: Jesse Webster is free after 21 years, granted clemency under an initiative meant to counter the wrongs of mandatory minimum sentencing. Mary Mitchell follows Webster’s journey from prison to redemption — part 1 of a 4-part series.

Jesse Webster was 27 years old when he was sentenced to life in prison for dealing drugs — in his first run-in with the law.

More than 21 years later, he is free, back home in the Chicago area thanks to a historic clemency initiative President Barack Obama began two years ago. A key part of this initiative that may well prove to be Obama’s greatest legacy was to free nonviolent drug offenders who once faced much harsher sentences than they would today.

His family couldn’t even comprehend how he could have been sent to prison for life.

They were pillar-to-post folks — the people we now refer to as the working poor.

His mother Robin had divorced his father and remarried, giving birth to three more children. She stopped working outside the home when he was a teenager.

His stepfather had steady work at a parking lot across the street from the East Bank Club, but he never made enough to keep the lights on and food on the table.

Webster, as the eldest child, tried to pick up the slack. He started hustling odd jobs in the neighborhood while still in elementary school — working for tips at a carwash, shoveling snow, carrying his neighbors’ groceries home for them from the Jewel.

But by first year in high school, he was selling drugs. At first, he was just driving a neighborhood drug dealer around in the dealer’s flashy car. It didn’t take long, though, before he was seduced into the drug trade.

“I was trying to help my mother pay on some of the bills and buy some food for our family,” Webster said in a letter to his lawyer explaining his background.

He was 26 when he was indicted in 1995 for possession and conspiracy to deliver cocaine — even though authorities didn’t find any cocaine.

When he heard the law was looking for him, he turned himself in. The entire family went with him to his lawyer’s office. They watched as he was handcuffed and taken away.


Follow @MaryMitchellCSTHe figured he could plead guilty and serve maybe five to 10 years.

But the feds demanded that Webster wear a wire and set up drug deals with members of the Gangster Disciples to help put away drug kingpin Larry Hoover, the gang’s founder. When he refused, he was hit with life in prison — a living death sentence.

And there was nothing anyone could do. The sentencing guidelines at the time of Webster’s conviction not only tied judges’ hands, they also gave prosecutors the leeway to pile on.

Webster was indicted on five counts: conspiracy to possess with intent to distribute cocaine, possession with intent to distribute, attempting to possess and two counts of filing false tax returns. Someone flipped on him, testifying how much cocaine Webster had sold, and Webster was found guilty of four of the charges.

Under the guidelines, U.S. District Judge James Zagel sentenced Webster to life in prison and fined him $25,000 but also offered his blunt assessment that the sentence was “too high.”

Webster was stunned.

“I never thought I would be there for life,” he told me. “But you know what, I woke up every morning thinking, ‘I’m still here, I’m still here.’ ”

At the height of the nation’s War on Drugs, tens of thousands of non-violent drug offenders were given similar prison terms. The result for the black community was catastrophic — so many young black men swept into prisons that the War on Drugs quickly became a “War on Families,” leaving behind thousands of fatherless children.

Webster’s own father had been in and out of prison. He lost contact with him when he was just 6 years old.

Webster had been in for 14 years and had lost several appeals when he crossed paths with Jessica Ring Amunson, a partner with the law firm Jenner & Block working in its Washington, D.C., office. A federal appeals court had appointed the firm in 2009 to represent Webster in his last, and final, appeal.

It failed. That left petitioning the president for clemency as Webster’s last, if dim, hope.

“The chances of receiving a clemency at that time was really slim and close to none,” Webster told me.

President Obama had commuted the sentence of only one person: Eugenia Jennings, a downstate Illinois woman who had been sentenced to 22 years for distributing cocaine.

Jessica Ring Amunson: “I could not understand why someone like Jesse would be spending the rest of his life in jail for a non-violent drug offense.” | James Foster / Sun-Times

Jessica Ring Amunson: “I could not understand why someone like Jesse would be spending the rest of his life in jail for a non-violent drug offense.” | James Foster / Sun-Times

“I was very honest about how much the odds were against it,” Amunson told me. “But I decided to take on his clemency case because I could not understand why someone like Jesse would be spending the rest of his life in jail for a non-violent drug offense. It just made no sense to me that our criminal justice system would work that way.”

By 2013, when Amunson was putting together Webster’s petition, the tide had turned against mandatory minimum sentencing as a cure to the nation’s drug ills. Amunson was able to get the two prosecutors on Webster’s case and Zagel to support the clemency petition.

“I didn’t think he would do it just because I was a young black man from the neighborhood out here selling drugs,” Webster said. “I mean, he’s the judge. I was ecstatic.”

Zagel declined my request for an interview.

Webster filed for clemency in 2013 — a year before the Obama White House announced a clemency initiative.

“It was as if they had taken Jesse’s case and turned it into the criteria for the initiative because he fit all the criteria,” Amunson said.

On March 30, 2016, Webster finally got the news he’d been dreaming of: The president had commuted his life sentence.

Warrant of clemency granted to Jesse Webster. | James Foster / Sun-Times

Warrant of clemency granted to Jesse Webster. | James Foster / Sun-Times

The lifer was hunched over a keyboard in computer class in prison, about to take a typing test, when he heard his name called over a loudspeaker:

“I go in the office, and they hand me the phone and turned on the loudspeaker.


“It was Jessie. I knew then what it was.

“ ‘You did it, you got it,’ she said.

“ ‘Your release date is September 26.’

“I just sat there.”

All he could say was, “Wow. Thank you.”


The federal sentencing guidelines for drug crimes were always unjust. They became the catalyst for the prison reform movement. Still, the issue didn’t get Obama’s attention until midway through his second term.

Apparently making up the lost time, the president has granted a flurry of executive clemencies since 2014. In fact, when he leaves office in January, Obama will have granted clemency to more than 1,000 federal inmates. That’s more than the previous 11 presidents combined.

President Barack Obama will have granted clemency to more federal inmates by the time he leaves office than the previous 11 presidents combined. | AP

President Barack Obama will have granted clemency to more federal inmates by the time he leaves office than the previous 11 presidents combined. | AP

Though historic, the total is a drop in the bucket. Thousands of drug offenders sentenced under the flawed sentencing guidelines remain languishing behind bars.

As the Obama administration comes to a close, civil rights groups are urging him to go further. A coalition of former judges and prosecutors as well as civil rights groups is asking Obama to grant “sweeping commutations” before he leaves office.

“With the stroke of your pen, you could change the lives of thousands of individuals and their families and write a legacy that will stand throughout history,“ the group said in a letter to the president.

Former U.S. Rep. Jesse Jackson Jr. has made his own plea, delivered via Facebook, for Obama to grant mass pardons. Jackson, who served time for looting his campaign funds, is also seeking clemency for himself.

It might turn out that Obama’s historic clemency initiative will be his enduring legacy.

The Republican-controlled Congress can unravel Obamacare, trash the president’s foreign policy and put Cuba back in a deep freeze. But it won’t be able to undo the commutations.

Webster is one of 395 prisoners whose life sentences have been commuted by the president. Now, how he does on the outside will help determine how a major piece of Obama’s legacy ends up being judged.

Jesse Webster with his now-grown daughter Jasmine and her son LaTrell. | Family photo

Jesse Webster with his now-grown daughter Jasmine and her son LaTrell. | Family photo

This is a story about Webster’s first eight months of freedom after spending 21-1/2 years behind bars. It’s also about what it will take to integrate ex-offenders like him back into family and community.

On April 12, 2016, Webster walked out of the federal prison in downstate Greenville. He wore a gray sweat suit and New Balance gym shoes. He carried with him phone numbers of people he had kept in contact with over the years, college-level textbooks, a list of books he wanted to read and a photo album of family members he’d left behind two decades ago.

By the time he returned to the real world, his mother was elderly, his baby girl was now the mother of a toddler, and the brothers and sisters he used to pick up from daycare had families of their own.

“You know, you wait for something so long that, when you finally get it, the burden is lifted off you, and it’s like, wow, it really happened,” Webster said.

Note: While clemency has restored Webster’s freedom, he believes he will never really be free of dangers tied to his past. So he asked that the last name of his family members not be published.


Part 2 — Walking out of prison

Part 3 — Halfway to freedom

Part 4 — Home at last

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