Matthew C. Crowl hadn’t seen Jesse Webster since 1995, when the former drug dealer was sentenced to life in prison for a first offense.

Crowl was a rising star at the time in the U.S. attorney’s office.

More than 20 years later, when Webster’s lawyer put together his clemency petition, she asked Crowl for a letter of support.

“I did it,” Crowl told me, “because I felt at the time that the life sentence was wrong. It didn’t seem right to the judge. It didn’t seem right to the U.S. attorney’s office. But back then there was no way out unless a witness cooperated.”

Which Webster wouldn’t do.

On March 30, President Barack Obama granted clemency to Webster and 60 other nonviolent drug offenders — not clearing them of their crimes, not proclaiming them innocent or changing their convictions, but reducing their sentences so they get out sooner.

After Webster was released, he wrote to Crowl, thanking him for his letter of support.

The former prosecutor suggested they meet for dinner.

“He was somebody that I never forgot, and there are very few cases that kind of gnaw at you all the time,” Crowl said.

It was the first time he’d ever had dinner with someone he sent away as a prosecutor.


As soon as Webster saw Crowl walk into the restaurant, he recognized him.

“Hey, Matt,” he yelled.

Matthew Crowl.

Matthew C. Crowl | Riley Safer Holmes & Cancila

Crowl greeted him with a hug.

“I was just very nervous that he would be bitter, but he was so generous and forgiving, almost as if there was nothing to forgive,” the former prosecutor said.

Webster wasn’t resentful.

“He did his job. My job was not to get caught, and his job was to catch me,” he said.

The government had wanted Webster to wear a wire and set up drug deals involving the Gangster Disciples.

At the time Webster was indicted, the U.S. attorney’s office was working feverishly to take down drug kingpin Larry Hoover, founder of the nationwide street gang, who’s now doing life in prison.

“The only reason we focused on Webster was because he was supplying the Gangster Disciples at that time,” Crowl said. “He would have been a perfect witness against Hoover. He was smart and didn’t have a criminal background.”

He still remembers how that conversation went.

“I told him we would give him a 10-year deal,” Crowl said. “He told me: ‘You can’t protect my family. My family is that big. They will kill my family.’ ”

Months later, Webster learned that one of the cooperating witnesses was killed execution-style. Webster decided to take his chances at trial.

“The surprising part was even when he was convicted, no one expected the guidelines to result in such a draconian sentence,” Crowl said of Webster. “We didn’t have an ounce of cocaine.”

Now, at dinner, the pair caught up with each other like old friends. Their daughters were born a year apart. While Webster was in prison, the former prosecutor had moved on to other careers, including a stint as first deputy chief of staff for Mayor Richard M. Daley. He is a co-founder of the Riley Safer Holmes & Cancila law firm. But he never forgot about Webster.

“I kept thinking here I was living my life, and he was living the rest of his life in prison,” Crowl said.

“Everyone realized the system got the wrong result,” he said. “Not in terms of conviction, Mr. Webster knew he was involved in the drug trade. But a life sentence was just not right.”


Before going to prison, Webster had never held a real job.

While Webster was at the halfway house, a friend of his lawyer got him an interview with Catholic Charities’ John Ryan, the chief of staff there.

“I pretty much made my decision when he walked in the door,” Ryan said. “His smile could light up a room.”

Ryan had hired other formerly incarcerated persons before. But he called Webster’s case “extraordinarily different” because of the amount of time he served and how he “rehabilitated” himself.

“We have other ex-offenders that work here that deserve a second chance, but I personally didn’t meet or interview them,” he said.

Victor Dickson, president and CEO of Safer Foundation, which helps ex-offenders, said about 4.1 million people with criminal records are living in Illinois.

About 4,000 clients of Safer Foundation are hired every year, though employers typically are quiet about that, according to Dickson.

“The people who have records and are getting jobs are the most loyal, committed and grateful employees,” Dickson said. “Some studies are now showing that people with records are as good or better by just about every measurement as a person without a record.”

Ryan could have hired Webster as a janitor. Instead, he offered Webster the opportunity to learn a new skill.

“I think all of these guys deserve and want a second chance,” Ryan told me.

A critical aspect of the re-entry process is the development of people so they can take advantage of such opportunities.

“What we try to do is work with people to get their GED, vocational training and industry recognized credentials so they can have the skills and credentials to go into a living-wage job,” Dickson said.


Jesse Webster, whose prison sentence to life without parol for a nonviolent drug offense was commuted by President Barack Obama, works at the Homelessness Prevention Call Center at the Catholic Charities of the Archdiocese of Chicago, Sept. 26, 2016. | Ashlee Rezin/Sun-Times

Jesse Webster, working in September at Catholic Charities’ Homelessness Prevention Call Center. | Ashlee Rezin/Sun-Times

Webster would get up at 6 a.m. each day and catch a bus from the Salvation Army halfway house to a Catholic Charities facility on the Near North Side where he referred callers in crisis to not-for-profit agencies that could help them.

“I might take 50 calls a day,” Webster said. “People just need somebody to talk to when things get overwhelming and life is just stressful.”

Noreen Russo, director of the Homeless Prevention Call Center where Webster worked, didn’t know about his criminal background before he came on board. But he made a point of giving her a copy of one of the news articles that had been written about him.

“I thought it was awesome,” she said. She found him a quick study. “He is willing to learn, which is such an impressive thing, and he learned quickly.”

Getting a job is one of the most important factors for someone with a criminal record to stay out of jail. There’s a 60 to 70 percent reduction in recidivism when someone has a job, Dickson said.

“Getting people with records employed would significantly cut the violence and crime in the city,” he said.


A few days before Thanksgiving, I met Webster for lunch. He was leaning against a wall when I walked up, head down, tapping on his cellphone.

After two decades behind bars, he is now trying to navigate the great changes that have occurred in that time — like the internet and relationships. Women he knew before going to prison now had great expectations.

“I’ve been gone 21 1/2 years. I’m not looking for a relationship. I’m trying to get used to this world. I want a relationship with this world,” Webster said, flinging his arms wide.

He was looking forward to the first Thanksgiving in more than 20 years that he would be able to sit at his mother Robin’s table.


Jesse Webster at home with his family the day after Thanksgiving. | James Foster / Sun-Times

Jesse Webster at home with his family the day after Thanksgiving. | James Foster/Sun-Times

While in prison, Webster called his mother every night.

“Why?” I asked.

“She’s my best friend,” he told me.

Later, his mother said the same thing about him. Leaning heavily on a cane and carrying an asthma inhaler, Robin, 66, plopped down heavily into a chair at the dining room table.

“I knew he was always a good person and that the life [sentence] would not stand,” she said. “He has always been looking out for us or the next person.”

As a kid, Webster used to cut school and sell drugs. But years down the road, when it all came out, his family stood by his side.

“Were you disappointed that Jesse was selling drugs and that is what got him in this situation?” I asked Robin.

“No,” she said emphatically. “I can understand him feeling like that, but I’m saying he did not.”

“No one sitting at this table ever thought he would have gotten life for that crime,” Webster’s brother Lee said.

All in all, Webster’s transition has been relatively smooth, though he finds he still has to adjust to being around family again.

“You’ve got to get used to that affection, that attention, that demand that comes along with being with family,” he said.

Some have called for more mass pardons and commutations from Obama before he leaves office next month. As a society, though, we are a long way from being ready to welcome these returnees home.

Stanley Balcom, a volunteer chaplain at the Cook County Jail who is co-founder of 7-70 Re-entry, a faith-based organization in Brookfield, said we should start by establishing a prison ministry at our local churches.

“Once they are out, we need to have a spirit of forgiveness, when those hands get extended to us to really reach for them without condemning and without looking down on them,” Balcom said.

It took a lot of caring people to get Webster back home safely.

Without them, he would still be wasting away behind bars.


Part 1 — From prison to redemption

Part 2 — Walking out of prison

Part 3 — Halfway to freedom

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

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