Chicago Sun-Times, Mary Mitchell: Jesse Webster – halfway to freedom

Jesse Webster, whose prison sentence to life without parole for a nonviolent drug offense was commuted by President Barack Obama, walks out of The Salvation Army Freedom Center on Sept. 26, 2016. | Ashlee Rezin/Sun-Times

Jesse Webster, whose prison sentence to life without parole for a nonviolent drug offense was commuted by President Barack Obama, walks out of The Salvation Army Freedom Center on Sept. 26, 2016. | Ashlee Rezin/Sun-Times

Third in a 4-part series

By Mary Mitchell, columnist

In commuting Jesse Webster’s life sentence, President Barack Obama gave the 48-year-old Chicago-area man a second chance at life.

It was “one of the most precious gifts a human being could give another,” according to Webster.

After more than two decades in prison, and then five months at a Salvation Army halfway house on the Southwest Side before being totally free with his Sept. 26 release, Webster was desperate to get on with his life.

He found out quickly it wouldn’t be easy.

Webster had been on the street only a few weeks when we met at my office. He was still worried something could go wrong and he’d end up back in a cell.

So was his family. When Webster told his brother Lee he was taking public transportation to get downtown, Lee nixed that idea.

“What if something happens?” his brother told him. “What if the bus breaks down? I’m going to get you an Uber.”

Webster kept a close eye on his watch throughout our meeting.

“It is really annoying,” he told me. “They release you and got you on a short leash. I have a job interview on Friday, and they told me they only got three hours for it.

It was the first time we had sat down face-to-face. He was shorter than he looked in photos showing him in prison garb, staring directly into the camera. In those, there was an intensity and also sadness in his face.

Now, that sadness was gone. But the intensity was still there.

Jesse Webster, whose prison sentence to life without parol for a nonviolent drug offense was commuted by President Barack Obama, sits down for a conversation with the Chicago Sun-Times, May 17, 2016. | Ashlee Rezin / Sun-Times

Meeting with Chicago Sun-Times columnist Mary Mitchell in May, Jesse Webster worried that if he got back to his halfway house late, “They can charge me with escape.” | Ashlee Rezin/Sun-Times

“If I am late, they can charge me with escape,” he said, explaining why he was so anxious. “The worst thing of all is if I get out on clemency and I am late and get charged with escape.”

After the interview, I drove him back to the halfway house. We stopped at a Popeyes on the way. The anxiety was still there.

“The first time I don’t get back on time,” he said, “they’re going to put a monitor on my leg.”

He was free. But freedom still felt elusive. And even after facing far worse for more than two decades, the restrictions now were a burden.

It irked him that a residential assistant at the halfway house had reprimanded him for stopping at a Dunkin’ Donuts without permission even though the Dunkin’ Donuts was right on the corner.

“I was two hours early, but they say you can’t deviate,” he said. “They call it a halfway house. But you only get 20 percent of freedom.”

In prison, Webster had developed a habit of putting his most urgent thoughts on paper. The habit stuck with him. In an essay he emailed to me, Webster complained that in the halfway house he was constantly being reminded he was “still in prison.”



In prison, Jesse Webster had developed a habit of putting his most urgent thoughts on paper. The habit stuck with him when he got out.



“Most residents are familiar with being looked upon with a disparaging eye from prison staff,” he wrote.

“However, to hear such words from the very person, outside the prison walls, who is assigned to guide and motivate a resident into wanting to be a productive citizen once they have been released from prison creates a bad omen.”

He expressed disappointment that halfway house residents weren’t allowed to have devices with internet access.

“The resident was denied an opportunity because he or she did not have access to the way the world communicates in today’s society,” he wrote.

Richard Hart, a spokesman for the Salvation Army halfway house, declined to comment on Webster’s complaints. Hart said the “residential re-entry” program that the Salvation Army operates for male and female former federal prisoners in Cook, DuPage, Will and Kane counties under contract with the federal Bureau of Prisons covers job readiness, resume preparation, online resume preparation, mock job interviews, money management and life skills and includes consultations with case managers.

Webster, who while in prison had taught re-entry workshops for other inmates, wasn’t impressed by what was offered by the Salvation Army.

“Like I never had a job,” he said. “There are a lot of guys like me that want to do the right thing. But if you don’t give them any opportunity to learn the skills to present themselves — soft skills, like how to use the computer — that is a challenge right there for a person who has been in prison. It is too easy to go back to your old life.”

Webster was particularly perturbed he couldn’t get a pass to spend Mother’s Day with his mother. It would have been his first with her in two decades.

Though free, Webster wasn’t having much fun. He wasn’t going out partying, he wasn’t hanging with old friends, and he wasn’t dating. What he did know to do to help him cope was to exercise.

“I have to go run just to balance out,” he said.

As soon as he was released from the hallway house, Webster planned to move in with his brother Lee and sister-in-law Tanesha.

“It was just adding another family member to the home,” Tanesha told me.

Webster was luckier than many leaving prison. It doesn’t help that for people with criminal backgrounds, the Chicago Housing Authority has a three-year wait before someone coming out of prison can get into public housing and a five-year wait to be able to get Section 8 housing.

Jonathan Holmes. | Chicago Coalition for the Homeless

Jonathan Holmes | Chicago Coalition for the Homeless

“You can’t find housing right away, and many people end up homeless,” said Jonathan Holmes, a policy expert with the Chicago Coalition for the Homeless.

The organization has a pilot housing program that allows re-entry providers to recommend clients for housing without them having to go through a wait period and is currently working with the CHA and the Housing Authority of Cook County to improve their policies on providing housing access.

Meanwhile, organizations like St. Leonard’s Ministries, which provides emergency housing for up to 40 men at its St. Leonard’s House, and 18 women at Grace House, both on the West Side, are trying to take up the slack.

“They come to St. Leonard’s because they don’t have any other place to go,” said Erwin Mayer, its executive director. “Some have been in prison a long time and are estranged from their families. And, in some cases, the family is engaging in activities that they don’t want to be a part of.”


Webster was so eager to leave the halfway house for good in September that, even before the sun came up, he had cleared out his belongings.

During his incarceration, Webster developed high blood pressure. The Salvation Army halfway house referred him to a clinic. But his medical bills, which the state was supposed to cover, hadn’t been paid in light of the state’s continuing budget stalemate.

Now, he was getting past-due notices for the medical treatment he received while in the halfway house’s custody.

“I’m getting mail about delinquent medical bills where they are trying to mess up my credit,” Webster told me in September. “They told me, ‘We’ll get it paid, but it’ll probably go on your credit.’ ”

Webster was frustrated. “This is a recipe to set you back,” he said.

The Bureau of Prisons declined to discuss Webster’s specific complaints. But a spokesman confirmed the federal prisons agency generally authorizes routine medical services, including medications, and later reimburses the costs of the services.

Webster also felt it was unfair for the halfway house to keep 25 percent of the gross income he earned from a job he had landed.

“I’m just coming home from doing a 21-year stretch,” he said. “I don’t have anything. How do you expect me to succeed if I can’t save any money?”

A Bureau of Prisons spokesman said the halfway house’s residents are required to make “subsistence” payments each payday but said the fee can be waived for indigent residents.

So Webster asked for a waiver.

“I still got to pay for the bus for work,” he said. “I’ve got to feed myself. And I have to wear clothes. We are not asking for a silver spoon. We are asking for an opportunity.”

He sees his experience at the halfway house as “arrested freedom.”

“Arrested freedom surfaces,” he said, “when ex-offenders are hindered and deprived of necessary tools to seize opportunities beneficial for everyday life.”

To read the full series, click here.