Courtroom 100 is on the first floor of Chicago’s dreary, neoclassical George N. Leighton Criminal Courthouse at 26th and California. And it is one of the dreariest rooms in the whole building. Unlike its wood-paneled cousins on the upper floors, this room has bleak, beige walls, PVC-tile flooring, and rows of uncomfortable wooden pews filled seven days a week by the anxious friends and relatives of the newly arrested. This room, where daily bond court hearings are held, is a gateway to the expansive machinery of the Cook County criminal justice system.

Here, a judge takes scarcely more than 30 seconds to assign a bail amount and give the defendant the next court date. As defendants grind through, they embark on a long, uncertain journey, beset with lucky breaks and unfair turns. Theirs are among the tens of thousands of felony or misdemeanor cases churning through the world’s largest unified court system. Whatever the outcome, these defendants are unlikely to encounter much personalized treatment.

Unless their case lands in front of Judge Jackie Portman.

Portman is an iconoclastic judge whose unconventional approach has won her countless fans—but also critics who question whether she’s overstepping the bounds of her office.

Just before the bond court call begins at 1:30 PM, the atmosphere in Courtroom 100 is decidedly more amped than its usual nervous torpor.

Portman swishes onto the high bench carrying her smartphone, a big, black cowbell with a red handle, and a carabineer jangling with keys and rewards cards.

“I require 100 percent,” Portman announces to a fresh batch of defendants lined up in front of her. “Everybody in this room is on 100. Every time we walk out of that door we are on 100.”

“Let me tell you what I will not take,” she continues, her voice loud and firm, rising for emphasis. “I will not take ninety-nine point nine nine nine nine . . . ” she trills on and on and on, the sound of repeating nines filling a courtroom growing tense with silent anticipation.

“NINE!” she ends, a good 30 seconds later. “One hundred is what I expect.”

Some of the defendants in front of her are smirking, some look stupefied. No one dares relax because they don’t know what to expect next. The staff milling around the bench, though, have heard it all before, and sometimes someone even sings along to the endlessly repeating nines.

Portman, a native of Englewood, runs two special programs at the Cook County criminal courthouse. One, known as the Deferred Prosecution Program, is designed for first-time, nonviolent felony offenders. Participants give up their right to a preliminary hearing in exchange for participating in the program for nine months to a year. If they fulfill all the requirements—like quarterly court appearances, paying restitution if it applies, and working, volunteering, or going to school—their charges are dropped and their arrest records can be expunged. Portman calls this her “second chance” program.

Her “last chance” program is Adult Redeploy Illinois, part of a statewide effort to reduce prison populations. Participants have been convicted of nonviolent felonies that could be punishable by prison sentences. However, within the program, they are instead offered probation if they comply with community-based drug rehabilitation and/or behavioral therapy in addition to school, work, or community service.

In this latter program, Portman is empowered to enforce compliance by briefly jailing participants for testing positive for drugs or breaking other rules. With the former, she can kick someone out for noncompliance; in that case, a defendant would then have to undergo prosecution for the original felony offense.

But neither of these outcomes happens often. Portman has her ways of motivating people to stay on the straight and narrow.

“I am not the typical judge,” she explains to a dozen “second chance” defendants huddled in front of her on their first day in the program. “I sing, I rap, I fuss, I dance, I shout, I flip, I do all kinds of stuff up here. Wanna know why? Because you’re not typical people. You made a mistake, you stood up and said ‘I made a mistake and I want to fix it.’ I applaud that effort. I am your biggest supporter.”

Portman wastes no time communicating her expectations in a well-rehearsed cadence. If “you do everything you need to do to take care of you,” she explains, “you will have noooooooooooooooooooooooo problem with me.”

But she warns: “When you mess up, I’m like the Incredible Hulk: You do not wanna see me angry. When I get angry, I lock people up. I’m known as the lock-’em-up judge.”

She warns program participants not to “play with the keys to their freedom,” thrashing her bulky carabineer in the air. And to get the point across about how important it is not to miss required meetings with pretrial officers, she paints a vivid picture:

“You go home tonight, you take a nice bubble bath, you all oiled down, you’re smelling good, looking good, chest just glistenin’, looking right. You got that tight outfit on, you got your house smelling like whatever your favorite meal is. Candles are lit, rose petals from the front do’ to the bedROOM, you got that favorite music on the radio playin’, be it Chris Brown, Rihanna, Beyonce, Neil Diamond, Julio Iglesias, whoever it is. And you watchin’ the clock, ’cause you know it’s gon’ happen TONIGHT . . . ” she pauses dramatically. “That person never shows up. You KNOW you’re gonna be mad. That’s how I feel when y’all don’t show up for their appointments. Because they set that time aside just for you.”

Even though this initiation spiel can seem intimidating, Portman’s softer, jocular side is just as readily on display. She inquires about defendants’ families, offers warm birthday wishes, and congratulates them on their achievements, such as going to therapy or finding housing. She vigorously rings the cowbell to celebrate every defendant who pays off restitution in full. When participants finish the program, she calls it “graduation” and toots a spirited rendition of Pomp and Circumstance through her lips.

“I appreciate you,” is a phrase Portman uses often. She greets everyone politely and inquires about their well-being, making empathetic eye contact. “How are you, kind sir?” she always begins with the men; she calls all the women “ma’am.”

While the typical demeanor of a Cook County judge is somewhere on the spectrum between boredom and impatience, Portman’s style is both maternal and authoritarian, like a tough high school principal or a strict grandmother. She adds an intensely personal touch to defendants’ daunting interactions with an often inscrutable court system.

Last winter, the sister of a young man killed in a Walmart parking lot appeared before Portman. The judge expressed her condolences and deep appreciation that the woman made her court date despite this tragedy. “My heart and my prayers go out to you and your family at this time,” Portman told her, leaning forward for emphasis.

That same day the judge had her bailiff and the relatives in the pews in stitches as she terminated a young man’s probation early. The man’s grandmother and uncle were in the pews with him. The grandmother announced that she was planning to move to Texas to save her grandson from the Chicago streets. She yelped with joy at the news of the early termination, and said she wanted to get the man married off too.

“Any takers?” Portman called out. “I’m a judge, we can do this right here, right now!”

As far back as she can remember, all Portman wanted was to be a judge.

Even though she was elected into the Fifth Judicial subcircuit in 2008 and has been retained since, there is not much information about Portman online besides campaign donation websites that list her parents, sister, and pastor as her biggest contributors. But she jumps right into telling me her life story minutes after I meet her in the chambers she shares with six other judges behind Courtroom 100.

Her father is the son of Irish immigrants; her mother came to Chicago from New Orleans during the Great Migration. After they married—much to the displeasure of her father’s Catholic community—the couple settled in the heart of Englewood and raised four daughters. Portman was the youngest.

“I never had a problem with being mixed, even growing up in Englewood being mixed,” Portman says. “A lot of people are like, ‘Did you have issues growing up?’ Because of my white face.”

She adds that her light skin drew some skepticism from voters when she was campaigning for her judicial seat. The Fifth subcircuit encompasses swaths of the south side from the lake to Western, between 26th and 75th Streets. “Of course the high yellowness of my skin made them ask if I was like them, really like them.”

Portman wastes no time establishing her south-side credentials in the courtroom. “I love when [defendants] come to court and they don’t know I’m from Englewood,” she says. “They tell me they were over on 63rd and Damen, or they were over on 67th and Ashland. Oh really? So you’re telling me that you went to the store. Did you go to the church right around the corner?”

The judge relates to her defendants in a way that she thinks will get them to take her and the program seriously. Though she won’t change her approach to suit who’s in front of her, she takes special care to connect with the young people coming from her own neighborhood. She wants them to know that she knows where they’re coming from.

“I give them real-life examples to show them that I’m not just saying that I live there,” she says. “I’m not just saying that I know the areas—I’m from the areas.”

Portman moved from Englewood to another south-side neighborhood shortly after she first began campaigning. She says an opponent distributed pamphlets with pictures of her family’s Englewood home, and she no longer felt comfortable having her parents live there.

“I still go back to the neighborhood all the time,” she is quick to note. “I really do think that kids need to understand that.”

Portman says it’s important for her to stay involved with her community and tell her story in order to show young people from the neighborhood that they have people to look up to among them.

“Everybody says [Englewood] is such a bad area, or such a bad place to be,” she explains. “It’s not. You make it what you want it to be. I came through the shootings just like everybody else. I walked past the drug dealers just like everybody else. But I still went to school, I got my education, I didn’t get pregnant, I didn’t get hooked up on drugs, I didn’t get into criminal activities. I was able to stand, and be an island, and do what I needed to do to take care of me.”

Portman also grew up around law enforcement. Her paternal great-grandfather had been a Chicago cop for 35 years; an aunt and sister worked for the sheriff’s department. She remembers going with her mother to drop her aunt off at work and seeing judges in the parking lot of the courthouse.

“I would sit there and think, man, who are these people?” She made up her mind about her future at the age of seven, after her aunt explained what a judge did. “I lived my whole life towards that,” she explains. “I had friends who were doing stuff they shouldn’t do and I was like, I can’t hang with you all. I gotta be a judge.”

After graduating from Maria High School, Portman double majored in political science and criminal justice at UIC. She went on to Thomas Cooley Law School in Michigan and scored a job with the Cook County state’s attorney’s office while she was still in her last year of school. Portman was a prosecutor for seven years before becoming general counsel at the Office of Professional Standards (now the Independent Police Review Authority) in 2005.

Three years later, before she even turned 40, her childhood dream came true.

Portman was one of the rotating bond court judges until early 2012, when the chief judge asked her to take over both the Deferred Prosecution and the Adult Redeploy Illinois programs. Until then she was one of a number of judges on these calls. But Portman’s ability to connect with defendants set her apart from her peers. She was willing to go far beyond her expected role as a judge to help defendants succeed in untangling themselves from the criminal justice system.

On an early November afternoon Portman enters a converted loft building on a postindustrial stretch of Cermak Road in Pilsen. She is out of her robes, wearing a light beige dress, a necklace made of shiny beige beads, and matching lipstick. Her face is carefully made up. “I just came from court,” she says apologetically. Normally, she likes to dress more casually on these visits, to show a more down-to-earth side of herself.

The building is home to WestCare, a health and human services agency that partners with the Cook County probation department to provide counseling services and other social support to defendants.

After she arrives on the fourth floor in the creaky industrial elevator, the judge presses herself against the exposed brick wall of a corridor leading to large, airy meeting space. Slowly, cartoonishly, she edges along, and peeks around the corner. Several men sit around a U-shaped table, their backs to her.

Portman sneaks up, nearly reaching them before she raises her voice in gotcha tone: “Who’s late? Who’s late? This can’t be the whole class!” A man turns around, his face registering surprise, then recognition. “It’s you!” he says, grinning. Just then another man walks in, tardy for the 1:30 PM group therapy session. His walk slows as he edges away from Portman in mock fear. She turns him around and points to a giant clock showing 1:35. The men at the table burst out laughing.

Every so often, Portman pays a visit to WestCare, where at any time about 50 to 60 defendants from her ARI program participate in counseling services. The goal of these appearances, she explains, is to show her defendants that she’s there to support their positive efforts, not just punish them. In the past, she has also come to the funerals of defendant’s’ relatives, made house calls, gone to her defendants’ sports games and music performances.

She does not intrude on the actual counseling sessions, but gives the staff a heads-up and, as she has today, comes a few minutes beforehand to give a pep talk, and school any latecomers about the importance of being on time.

With Thanksgiving around the corner, she chats with the men about their holiday plans, and the proper way to cook chitlins. She counsels a young man who arrived with a cut in his palm on how to dress and care for the wound.

At first the WestCare staff were apprehensive about these visits, and about the consequences of a judge appearing in defendants’ lives outside the courtroom. But their fears were quickly dispelled, according to the program’s director Gwen Maxwell.

“I have never encountered this,” she says of Portman’s approach. But, she clarifies, the judge’s sincerity caring for defendants is palpable. However unorthodox it may be for Portman to cross the usual boundaries, to Maxwell and her counseling staff it seems like a step in the right direction.

“We talk about bridging the gap—bridging community and law enforcement, bridging community and the legal system,” Maxwell explains. In her view, that is exactly what Portman achieves with these visits. “She’s not designed for [defendants] to continue to be locked up.”

As Portman continues talking with the men in the meeting area, periodically inducing roaring laughter, John Greenlees, the assistant public defender assigned to the ARI program, walks in. He is surprised to see Portman at first, but they quickly get to talking about one defendant who has not yet shown up for the group meeting.

Greenlees comes by WestCare’s offices often, since many of his clients do not have reliable phone access or stable addresses where he can reach them. Today he’s here to warn a man who is having some difficulties complying with ARI requirements that he needs to get his act together. Portman is also concerned about this defendant. They wait together by the elevator, and when the man finally appears, they scold him for being late. The process does not appear adversarial; the lawyer, the judge, and social worker Darryl Cooke all team up to convey that the man cannot be late without giving notice. They’re there to help, but he must communicate if he is having trouble doing what he needs to do.

Is this what criminal justice reform looks like?

“Yes,” Greenlees says unequivocally.

In an office, away from his group, Cooke reflects on the therapeutic value of Portman’s outreach. He leads cognitive behavioral therapy sessions with ARI defendants.

Like Maxwell, Cooke was first suspicious of having Portman there.

“We’ve been pleasantly surprised,” he says. His main concern was that her presence would undermine his clients’ trust in WestCare as a place where they could speak freely. He soon saw, however, that Portman’s appearances reinforced his own messages to his clients.

“When guys come to the program, they identify everybody in the criminal justice system as the enemy,” Cooke explains. “She talks directly to them like a family member.” Cooke says that many of the men he works with suffer from trauma and a life of abandonment and neglect. In some ways Portman is rebuilding trust that was lost long before these defendants entered her courtroom.

“You’d be surprised when was the last time they had somebody come in that told them they was doing a good job and gave them a hug,” Cooke says. “They don’t receive that on a daily basis. So to get it from somebody that you view as superior to you is an overwhelming feeling.”

Portman’s informal hands-on approach is not without critics, and she knows this well. In the past, observers from municipal and state judicial monitoring organizations have taken issue with her informality.

When she initiates defendants into Adult Redeploy Illinois, for example, she schools them on the consequences of trying to fake their drug-test results, pulling out a Whizzinator in court. The device is basically a fake rubber penis attached to a bladder that can be filled with someone else’s urine. “It’s not to shock and chagrin and show profanity to the clients,” Portman explains. “It’s to tell them, ‘Don’t do this, because if you do, you’re gonna get a new felony charge and get locked up again.'”

Portman says she has been criticized for yelling in the courtroom too—for pointing her finger and for saying, “I’m gonna lock you up.”

Indeed, when the Chicago Council of Lawyers released its evaluation of judges up for retention in 2014, they noted that a “few defense counsels complain that she can get inappropriately ‘animated’ in the courtroom, but most respondents praised her temperament.”

Portman points out that some of her critics, who arrive for brief, one-off visits, can’t understand the efficacy of her approach. “When I took on [ARI], I tailored my attitude and my demeanor, and how I speak and the examples that I use to the crowd, on a level that they could understand.”

However, some criticism has gone beyond her methods. “I had one complaint I’ll never forget,” Portman says.

“They told me I speak in an ‘Afrocentric tone.’ And I said, ‘Well first: What is an “Afrocentric tone?”‘ They were saying I was talking down to the defendants in this ‘Afrocentric tone,’ and I said, ‘Well it’s kind of difficult for me to address that because I don’t know what an “Afrocentric tone” is, one. And then two, I’m Afrocentric, in case you didn’t know. Born and raised in Englewood, spent my whole life there, don’t know any other way to talk. This is how I talk.'”

Portman says the racial undertones of the criticism were offensive: “I’m part African-American, so are you saying something’s wrong with the way I speak?”

However one feels about Portman’s demeanor, her approach sparks the larger question of whether the criminal justice system can be reformed through the personalized stewardship of judges like her. And even if it were possible to populate Cook County courts with dozens of Portmans, would that be desirable for the administration of justice?

Attorney Ali Abid says no. Abid is a policy analyst at the Chicago Appleseed Fund for Justice, an organization devoted to researching and helping implement reforms within the criminal justice system.

“Certainly one of the things we need in the criminal justice system is more humanization,” Abid says. But he also argues that the risk with Portman’s beyond-the-courtroom outreach is that information starts to flow in ways that could ultimately hurt defendants.

“You have lots of information that’s going to the court, directly to the judge, that may affect the decision making that’s happening, outside of the presence of the defendant’s attorney,” Abid explains. “One of our bedrock principles is that a defendant should be represented—that they should have control over what information goes and doesn’t go to the courts in order to defend their rights. And a judge showing up to a group therapy session, following that person out of the courtroom into other aspects of life, circumvents a lot of the infrastructure that’s set up to protect people’s rights.”

Moreover, Abid adds, even if these out-of-court interventions have worked in Portman’s programs and for her clients, there is no way to standardize her methods. Judges are not trained to do social work, nor could we count on all of them to do it right.

“You can’t expect every judge to be equally good at understanding the nuances of group therapy, of individual therapy, of drug test results, of all the other things that are happening,” he says. “You’re not going to get on board massive criminal justice infrastructures, involving dozens and dozens more judges, hundreds of other state’s attorneys and public defenders, and treatment providers, to all know how to behave in this new way where a judge can just show up and be expected to act responsibly on all the information that they’re getting.”

Instead, Abid says, to achieve true, lasting reforms, we need more programs like DPP and ARI, which involve a coordinated team of specialized professionals who work with defendants on various aspects of their cases and their lives, which have checks at various levels. Cook County already has more than 30 specialty courts in addition to Portman’s, ones that deal with veterans, the mentally ill, and other types of offenders. But very few defendants get access to these courts, Abid says.

Still, Abid says, Portman’s work and the positive response to it show that “there is a demonstrated need for looking at defendants in a more holistic way, as whole human beings with needs and goals that need to be worked upon and assisted with to rehabilitate them.”

Portman’s impact on the lives of defendants who pass through her courts can’t be denied, even if she’s destined to be a one-of-a-kind phenomenon within the Cook County criminal justice system.

Avery Brady, 60, was one such defendant. Brady’s parents, like Portman’s mother and many other black Chicagoans, came from the south. His father, Avery Brady Sr., was a noteworthy musician, playing an unusual repertoire of his own Delta blues songs at private parties and clubs around the city after World War II.

Brady Jr. was the baby of the family. He remembers his parents’ house parties and his father teaching him to play guitar.

Eventually Brady became a blues musician in his own right, playing bass guitar with A.C. Reed and other famous acts in the 1980s. But, Brady says, he got hooked on drugs, and his addictions to heroin and cocaine predictably took over his life.

On a February morning in 2013, Brady and a friend went out looking for scrap metal and other valuable materials in Austin, to sell for money to buy drugs. They came to an abandoned house and were about to make away with a bathtub when someone called the police.

Avery spent about a month and a half in Cook County Jail before being released on probation, he says. He started using again as soon as he got out.

His probation officer’s patience wore thin. “She put up with me for about six months, let me get high,” Brady remembers, “then she recommended me to a probation officer at 26th and California.” This was how Brady wound up with Portman as his new judge, in the Adult Redeploy Illinois program.

The first time he tested positive for drugs she locked him up for three days. He knew that this time he had to start taking the probation terms seriously. “I drunk plenty of water, cleansed my system of the little cocaine I had smoked,” he says. “When I came back and took my drop, it was clean.” From there, Portman released him from jail and sent him to WestCare, where he met Maxwell and Cooke.

Looking back, Brady thinks Portman was fair and sincere. “She was just a real lady, and I think she’s a good person,” he says. “If you do what’s right, she’s gonna do you right.” He says he had never seen a judge like that before.

Brady thrived at WestCare. He started bringing his guitar to play for the other clients and staff. One day, he invited everyone to come see his gig at Lee’s Unleaded Blues, a legendary south-side blues bar that has since gone out of business.

Brady was playing with vocalist Willie White and a four-man band. They were about three songs in, and the bar was packed, when “Gwen, Darryl, and all of them came,” he remembers. “They said, ‘We’ve got a surprise for you.'”

Portman was there, rounding out his support team in the bar.

Maxwell remembers how elated Brady was to see the judge. “His eyes lit up! He came on over and he was like, ‘Wow, you said you’d do this, but I wasn’t expecting it!'”

Brady says his bandmates were impressed, and he was proud to have “his judge” at the show. It meant a lot to him to have someone that important show up to support him.

“I think it was a blessing for all of them to come out,” he says. “It was a real good feeling. It made me feel that I am somebody. That made me stronger.”

Portman recalls it as “a wonderful night.”

“He kept saying, ‘My judge is here! My judge is here!'” she says.

“I saw pride,” Cooke adds. “That’s an acknowledgment. You never see people put a judge in the same category as some celebrities, and that’s what happened that night.”

“And ever since that day I’ve been moving up,” Brady says. “No getting high, no nothin’.” Brady hasn’t had any new arrests since he successfully completed ARI.

He now lives in Austin, playing occasional shows around town and in his church band. He doesn’t like taking the bus and is working on restoring his driver’s license. Once he does, he plans to pay Cooke and Maxwell a visit at WestCare, and to go see Portman too.

“One day I’m gonna go to court and I’m just gonna sit there, just listening to her,” he says. “If you hear from her, tell her I’m not getting high and that I’m still doing real good.” v