The trials of Stuart V. Goldberg, Chicago’s flashiest defense attorney | Feature | Chicago Reader

The trials of Stuart V. Goldberg, Chicago’s flashiest defense attorney 

He wears $5,000 suits and is chauffeured to court in a Rolls-Royce. He’s made a fortune off the war on drugs. He claims Oprah once wanted to have his baby. He is the most interesting lawyer in Chicago. But who’s the man behind the megawatt smile?

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Stuart V. Goldberg - KEVIN PENCZAK / ASSISTANT: SNAKEBITE
  • Stuart V. Goldberg
  • Kevin Penczak / Assistant: Snakebite

In a half hour Stuart V. Goldberg needs to be in three different Chicago courtrooms dozens of miles apart. It's 8:30 AM on a Tuesday in October 2016. He takes off the jacket of his gray, three-piece Tom Ford suit before sliding behind the wheel of his white Rolls-Royce.

He is a man of many mantras and rituals. "If you don't take your coat off while you drive you're like the hundred other lawyers in court with a wrinkled suit," he says.

Goldberg is widely known in local legal circles as one of the city's busiest criminal defense attorneys. He swings by to pick up his nephew Matthew Kaplan, then a student at Goldberg's alma mater, John Marshall Law School. The 27-year-old will drive his uncle from court to court, semireclined behind the wheel, assisting him in preparing arguments and drafting motions throughout the day.

Goldberg gets on speakerphone. "Linda, you're doing a great job!" he announces earnestly to the courtroom clerk who picks up. "Running a little late." He asks her to push his case to a later slot on the morning's docket. "R.J., what's up, it's Goldberg," he says to the next clerk on his speed dial. "Just pass it for me." Whichever judge he knows to be the strictest about starting hearings on time, it's his or her courtroom he heads to first.

No sooner does Goldberg walk through the doors of a courthouse than people begin approaching to ask for his card. ("They're hand engraved," he likes to point out. He estimates that he's handed out a quarter million of them over the years.) Guards, other lawyers, and judges greet him as he floats by, back straight, leading with his chest. No matter how short he is on time, he never looks rushed. "The way I dress, the way I act, the way I walk into a courtroom is all part of the brand," Goldberg later tells me.

Entering a courtroom in Pullman on the city's far south side, Goldberg—a dead ringer for Michael Douglas in Beyond a Reasonable Doubt, with his silver mane and angular features—struts past rows of pews filled with mostly black men, women, and children, and then two filled with mostly white cops. He shakes hands with one of the officers, then goes to talk with his client's girlfriend. Her boyfriend, Llewain Hardin, was out on bail on a different drug case when he was arrested with 41 small bags of crack cocaine and 13 baggies of heroin—enough to land him a few years in prison if he were convicted.

Llewain was supposed to lay low while Goldberg worked to resolve his other case, but "he didn't listen to me," Goldberg says. "The drugs were found on him." At the preliminary hearing today the judge would decide whether there was probable cause to suspect that Llewain committed the felony and if so, send the case on to be prosecuted before the same judge who was hearing the first case. This would make defending Llewain on both sets of charges harder. "The officer was an honest officer. He wrote a good report," Goldberg notes, scanning the arrest report for red flags and inconsistencies. In the margins he'd scribbled some notes in purple ink.

When Llewain, a tall black man with dreadlocks, is brought into the courtroom from lockup in a beige jumpsuit, the same police officer who'd shaken Goldberg's hand approaches the judge's bench. The prosecutor, a young white woman, questions him about the arrest. He testifies that a call had come in about a drug dealer, and when he arrived on the scene he saw Llewain sitting on a stoop. As he approached he says he saw "a bulge" in Llewain's waistband and proceeded to frisk him, thinking it could be a gun. The bulge turned out to be a package of drugs wrapped in individual doses seemingly ready for sale.

On cross-examination of the officer, Goldberg focuses on the details. Despite his flashy appearance there's no bombast; in and out of court Goldberg is soft-spoken, patient, and methodical. He questions the cop about what the 911 caller had reported—drug sales in progress—and what the officer saw when he arrived on the scene—a man loosely matching the caller's description sitting on a stoop. Goldberg asks about the bulge that looked like a gun. The officer says that during the pat down he felt it was "soft." Goldberg zeroes in.

During a preliminary hearing, attorneys are not supposed to argue about the evidence for charges, only about the grounds for arrest, and so the prosecutor quickly objects when Goldberg turns to the judge and cites Minnesota v. Dickerson. But the judge looks interested and lets Goldberg keep talking. This was a 1993 Supreme Court decision stating that if a police officer is frisking a suspect for weapons and feels an object that he knows isn't a weapon but can't tell what that object is, then continuing the search and seizing the object is unconstitutional, even if it turns out to be contraband.

The moment the cop felt that the bulge in Llewain's waistband was soft, he knew it wasn't a gun and had to stop the search, Goldberg argues. "We're hoping for judicial economy," he concludes—a signal to the judge that the case would fall apart later since the evidence couldn't be used against Llewain anyway and that it would be pointless to let the arrest stand and tie up the next judge's docket. The judge agrees. "There is a finding of no probable cause," he says and calls the next case. Spinning around toward her colleagues, the Cook County assistant state's attorney mouths "I can't believe it!" with eyes bulging. Llewain grins as a sheriff's deputy leads him out of the courtroom. He'll be released later that afternoon.


—Stuart V. Goldberg


"That was near impossible," Goldberg tells Llewain's girlfriend as he makes his way out of the courtroom. Before he reaches the door two more people ask for his card.

As he entered his 70s, Goldberg's career was on fire: up to a dozen courtroom appearances for different clients every day, three bench trials every week, a jury trial once a month. After every win in court—whether a not-guilty verdict, a successful motion to suppress illegally obtained evidence that gets his client's case dismissed, or a finding of no probable cause for arrest—Goldberg posted a celebratory picture of himself with his happy clients on Instagram and Facebook. Below, dozens of followers and friends left notes of gratitude, words of congratulations, and pleas to represent them. Like Saul Goodman, the fictional lawyer who helped Walter White get out of many a legal pickle in Breaking Bad, Goldberg has a knack for making cases disappear, and it's earned him a loyal clientele among Chicagoans living at the intersection of crime and police overreach. Caught with two pounds of marijuana? Better call Stu. Cops seized three assault rifles from your home? Better call Stu. Pulled over by police and charged with a DUI for that cough syrup in your cup holder? Better call Stu. (But when you call, you better not call him Stu—it's Stuart.)

Regardless of what crimes his clients—most of them young, black men—may or may not have committed on the streets, in Chicago, and across the country, they're usually treated by cops, prosecutors, and judges as guilty until proven innocent. They're usually poor and represented by overburdened public defenders. If they have the money to get a lawyer they're more likely to wind up with a shark. Their constitutional protections against unreasonable arrest and unwarranted search and seizure as well as their right to a speedy trial are rarely affirmed. According to a report from the Cook County state’s attorney’s office, 57 percent of black defendants in the county found guilty of a felony in 2016 were sentenced to prison time, compared to 36 percent of white and 39 percent of Latino defendants, who were more likely to get probation. Of the 11,000 people sent to Illinois prisons from Cook County in 2016, 74 percent were black. In this moment, Goldberg—with his virtuosity in oral arguments, encyclopedic knowledge of the law, and categorical refusal to consider plea bargains in all but the most extreme circumstances—is exactly the kind of champion they need in court. But the man who's been reversing their odds case by case isn't on a social justice crusade to undo the policies that produce his client base. He sees himself as a foot soldier in the battle between good and evil—humanity's noble intentions and our tendency to make bad decisions, ordinary people's attempts to keep their heads above water and the government's incessant drive to limit their options for doing so. It's a battle that's cost him friends, family, money, and even for a time, his career. Surviving a lifetime of snatching people from the jaws of the justice system has required a knack for reinvention and a thick, protective armor.

On Instagram and Facebook, Goldberg often posts celebratory pictures of himself with his happy clients. - VIA @GOLDBERGCRIMINALDEFENSE
  • On Instagram and Facebook, Goldberg often posts celebratory pictures of himself with his happy clients.
  • Via @goldbergcriminaldefense

Goldberg exits the courthouse just as Matthew pulls around in the Rolls. He drops his white Hermès briefcase in the trunk and snaps the lid shut. The license plate reads SNKCHMR—snake charmer. It's how he's come to think of himself, as a tamer of the "evil forces at 26th and California that will push you into trouble."

He's come a long way from his working-class upbringing in West Rogers Park. Neither of his parents, children of Jewish eastern-European immigrants, went to college. His father didn't finish high school. Goldberg was the eldest child and only son; his three younger sisters, he says, set him up to be a "woman's man, not a man's man." He never watched or participated in sports; his favorite pastime has always been "a one-on-one conversation."

He describes himself as a short kid, "definitely a late bloomer," who allied with the biggest, toughest kids in grammar school to protect himself from bullies. He got in trouble a lot. Teachers regularly sent notes home: "Does not play well with others." "Doesn't come organized." "Talks unnecessarily." Though he wasn't a particularly good student, Goldberg had a fierce competitive streak and sought out leadership roles, like being hall monitor "lieutenant," which entitled him to a badge with three stars and authority over others. "When I was in a group, I wanted to be the top of the group," he says.

By the time he got to college at the University of Wisconsin-Madison in the late 60s, he was already thinking about a career in law. Goldberg recalls Madison resembling a war zone: mass protests against the Vietnam war, activists bombing buildings, police in riot gear hurtling tear gas. But he was utterly uninterested in politics and resented the protesters disrupting the functioning of the university. "I just wanted to get to law school," he says "I did originally lean a little bit toward law and order."

Drug use was also rampant. "They thought I was some kind of undercover narc in Wisconsin because I was so straight," Goldberg says. He didn't use, smoke, or drink—still doesn't—having grown up in a home where alcohol was only around on Passover, when drinking the sugary wine "was like tasting piss." (There's a nonalcoholic cocktail called the SVG at one of his favorite stops, Le Colonial, the upscale Vietnamese restaurant in the Gold Coast. A bartender created it to match the lawyer's orange Lamborghini: lychee puree, mango juice, sour mix. Patrons can choose to add vodka.)

In his last year of college Goldberg was drafted. Months before his deployment to Vietnam, a congenital defect spared him: he was born with two kidneys on one side of his body, a condition known as fused renal ectopia. Because he thought he'd be deployed, Goldberg didn't apply to law school during his senior year at Madison. After graduation he returned to Chicago and began looking for work. He was hired as a Chicago Public Schools substitute teacher. At first he was sent all over the district, until one day he landed at Walter Scott, a grammar school on Blackstone Avenue in Woodlawn, where a teacher had left abruptly. The largely black school was understaffed and overcrowded. Many students had special needs, Goldberg recalls, but no special attention. He was assigned to a class of students who were behind on their reading skills.


—Stuart V. Goldberg


"They were ten, 11, 12, and they were my size," Goldberg says. "They beat up the last teacher and stole his car." He told me he felt for them but he was also overwhelmed by their behavioral problems. Almost immediately he had to send kids to the principal for fighting or refusing to work. But when they returned to class he was horrified to learn they'd been beaten; back then staff at CPS schools got away with corporal punishment. "The principals in the elementary schools in the inner city would have rulers taped together, or pointers, and they would whip the kids." Goldberg decided he wouldn't send the kids away anymore, instead inventing new rules for his classroom: he let them chew gum, created a point system to incentivize good behavior, and handed out prizes. By the week's end, he says, the students were begging him to stay on. "The kids signed a petition, and the parents, to have me come back. And sent it to the Board of Education." Goldberg ended up spending a year at Walter Scott. He says his students' behavior continued to improve as he positively reinforced them, and though he'd had no formal training as an educator, he was able to teach them reading basics. He played music on Fridays, letting boys and girls dance with each other. He took them riding in his car and out to eat lunch. "It was so rewarding. It was unbelievable," he says. "I got these kids to see that there was some other life. Every day I broke up a fight. I sewed their shirts together. Because if they went home with a ripped shirt, they would get beaten." He says students eventually started calling him Daddy Goldberg.

As the law school application cycle approached, Goldberg considered staying in teaching, but given "the difference I could make just as a teacher—my God, what difference could I make as their lawyer?" he recalls thinking. "I would be in charge of their lives. I could save them. When they stepped off that rock, I could save them."

Goldberg finally walked into John Marshall Law School in the fall of 1970. He met a real lawyer for the first time that day at orientation. The next year Richard Nixon declared drugs "public enemy number one," and as Goldberg immersed himself in his studies and drove a cab at night to pay his way, he began to see drugs as the base of a fledgling specialization. "It was my feeling that, in criminal law, drugs were the catalyst—the common denominator in most criminal cases," he says. He also had some personal experience with the criminal element around drugs: one night in Evanston a couple of dazed hippies held him at gunpoint, and he found himself having to negotiate the surrender of his day's cab fare earnings.

Illinois appellate court justice Aurelia Pucinski remembers meeting Goldberg at John Marshall in 1973, as he was preparing to graduate. He sat next to her on her first day of class, and "I thought, OK, he's a really hot guy." But then Pucinski recalls Goldberg turning to her and asking, "Do you have a game plan?" "I said, 'Well . . . what's yours?'" He announced that he planned to "get a job at the DEA," where he'd learn how they investigated and built cases against drug dealers. And then, he concluded to the young future judge, "I'm gonna go out and represent the biggest drug kingpin in America and I'm gonna be a millionaire."

Pucinski was impressed. She saw Goldberg a few more times before he graduated and then again periodically over the years. "Stuart Goldberg is living proof that having a game plan works," she says every time she tells this story, which is often, mostly to young people. "That was 1973 and I'm still talking about it all these years later. He's a guy who knew what he had to do to get to where he wanted to be. So God bless."

Goldberg didn't end up at the DEA. Instead his first job was with the Illinois Drug Abuse Program; he was an attorney for a network of state-funded rehab centers where people charged with drug possession could be sentenced as an alternative to incarceration. Less than a year after he entered that line of work, he saw that there was a huge client base among the participants and left to start his own private practice. Besides, he didn't like having a boss.

But being your own boss didn't mean being in charge of your professional life. What he quickly learned was that in the mid-70s, Cook County criminal courtrooms were a cesspool of corruption.

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Goldberg says there are five things to look for in a man—shoes, haircut, pen, tie, and watch. - KEVIN PENCZAK
  • Goldberg says there are five things to look for in a man—shoes, haircut, pen, tie, and watch.
  • Kevin Penczak

As the Rolls glides north on the Dan Ryan Expressway, past some of the most impoverished neighborhoods in the city, Goldberg is still reveling in the improbable victory he orchestrated for Llewain. I ask him whether he thinks Llewain will heed his advice now and stop selling drugs while his other case is pending. "No," Goldberg says without hesitation. "He's got a girlfriend that works hard, a hardworking girl that loves him. He's got children. I think it's weakness, stupidity, and ignorance, and an easy way to make a living, and that's probably all he knows."

Goldberg doesn't bring up the fact that Llewain's previous felony conviction would prevent him from getting most any legitimate job, though when the point is raised he agrees that it's true. Unlike criminal justice reform crusaders, Goldberg isn't prone to holding forth about bias and racism in the system, or the way that people's entrapment in it is determined by race and socioeconomic status. He says he's always identified with black clients because he understands what it's like to be an outsider—he's been the only Jew in many a room. But asked whether he thinks there's racial discrimination in the courts he seems to contemplate the notion as if he'd never before given it a thought. "Somewhat," he concedes finally.

Goldberg says he loves cops and respects prosecutors even though his job puts him in direct opposition to them in the courtroom. A self-identified Republican, he's pro-Second Amendment and disdains big government, and also thinks marijuana should be legalized. When he talks about his clients he's neither particularly sympathetic nor especially judgmental. "I'm not saying he's an honorable, perfect representation of a citizen of Chicago," Goldberg says of Llewain, "but if we are to operate under our law, I'm like a surgeon. They roll them in on a stretcher, I don't ask was it the cop, the bank robber, or the teller that got shot, I just take the bullet out. I do my job as a crucial part of the way the justice system works."

Ultimately Goldberg's outlook is that life isn't deterministic. He believes in the importance of personal choices, and in everyone's propensity to make bad ones. "We're in the business of man's inhumanity to man," he likes to say of his work. "We're in the mistake business."

As long as they can afford it, Goldberg's clients—the majority of whom are facing drug and weapons-related charges and come from neighborhoods besieged by aggressive policing and gun violence—can count on the second chances to keep coming. Some of his clients are ordinary people who might get pulled over driving someone else's car in which the cops discover a gun. Many face low-level pot possession charges. But some of his clients appear, based on the charges against them, to be deeply connected with criminal enterprises.

Goldberg considers the day's schedule and listens to some voice mails. The only way to reach him is by phone. He doesn't use e-mail because, he says, "e-mail is for pornographers." Though his business card lists an address on the 14th floor of a swanky Magnificent Mile building, Goldberg only occasionally shows up there to make use of a conference room. "Offices," he says, "are for guys sitting around waiting for the phone to ring."

His cars serve as both office and billboard—the ultimate marker of success and professionalism. The Rolls is always showroom clean. When excited young men run up to ask how much it costs, he likes to answer "a lot of not-guiltys." Inside there's not a single personal object in sight. In the trunk he keeps only purple manila folders that hold his clients' files and an Alexander McQueen umbrella with a skull handle. There are also a couple of small trays for the times he and Matthew get Portillo's on the go; with around 50 cases each week scattered across the county, that's not unusual.

"One of my most important client's son is up today," Goldberg says. Kolby Craig, known to everyone as Big Mo, "has referred innumerable people to me. Hundreds." Goldberg explains that in addition to beating Mo's charges on many occasions, he also "saved [Mo's] best friend's life. He had a kilo of cocaine in his lap." Mo has generously repaid Goldberg's services not only in tens of thousands of dollars in fees but in more personal ways as well. "When my son was born he went to a jeweler and had a tiny Jewish star made, all with diamonds."

Mo's son's case appears to be a formidable challenge. In March 2016, 18-year-old Stephon Mack was indicted on one count of possession of a controlled substance, four counts of armed violence, and 24 counts of aggravated unlawful use of a weapon. Goldberg managed to get Stephon out on house arrest, but he still has to prove the guns and drugs can't be used as evidence against the teen. As he scans the police reports again, Goldberg is unequivocal. "A clear case of the cops lying," he says.

Goldberg circa mid-70s with a 1974 De Tomaso Pantera. Illinois Appellate Court justice Aurelia Pucinski remembers meeting Goldberg at John Marshall Law School in 1973, as he was preparing to graduate. He sat next to her on her first day of class, and “I thought, OK, he’s a really hot guy,” she says. - COURTESY STUART V. GOLDBERG
  • Goldberg circa mid-70s with a 1974 De Tomaso Pantera. Illinois Appellate Court justice Aurelia Pucinski remembers meeting Goldberg at John Marshall Law School in 1973, as he was preparing to graduate. He sat next to her on her first day of class, and “I thought, OK, he’s a really hot guy,” she says.
  • Courtesy Stuart V. Goldberg

The moment in Stuart Goldberg's personal narrative in which it becomes hard to parse what's real and what's embellished is the mid-1970s. At that time judges in almost every division of the circuit court of Cook County were taking bribes to fix cases. Traffic tickets, divorces, drug charges—all could go away at the right price. When he talks about this part of his life, Goldberg begins by saying, "Now I'm getting into The Snake Charmer." This is the title of the autobiographical novel he's been working on for more than 20 years. It's his dream to see it made into a movie. Sitting at the Greek Islands on Halsted Street—another restaurant where everyone knows his name—he frequently distinguishes between events happening "in real life" or "in The Snake Charmer."

Goldberg says that when he began his private practice he saw the scales of justice being tipped, and it outraged him. What's more, the heavily Irish Catholic judiciary's anti-Semitic hostility toward him was palpable, he says.

"The whole system was ridiculously corrupt. You had to give money to the clerk to get your cases called. If you weren't in the club of people paying off the sheriffs, the cops, the judges, it was very difficult to break in." Even in his custom-made black three-piece suit and leather cowboy boots he says he felt invisible, waiting all day in narcotics courtrooms for his turn in front of the judge.

"The way it worked was, you walked up to the clerk and you had $10 in your hand. The clerk would open the drawer or the clerk would push the wastebasket out, and you dropped it in the basket or the drawer, and your case was called." The sheriff's deputies would also make a cut by directing confused defendants to attorneys who played ball.

Was he ever tempted to participate? "No, that's not my style," Goldberg says. "I'm too much of a rebel." During one of our conversations about The Snake Charmer, he quotes a favorite passage from the book inspired by his experience with courtroom corruption: "Is it bribery when you pay a judge, to give money for the person you're representing to get off? Or is it extortion when you can't represent them unless you pay money?"

By the late 70s the circuit court was the target of a massive undercover FBI investigation code-named Operation Greylord—the largest judicial corruption sting in American history, which involved the wiretapping of judges' chambers and undercover operatives paying to fix cases. Sources close to the operation say that Goldberg wasn't involved with the federal efforts to bring down the judges, and no one I spoke with had heard of Goldberg being one of the corrupt lawyers who was targeted by the investigation. Still, in his recollection he was close to the action in the Greylord years.

Goldberg says that as his struggle to get his clients' cases called continued, he began to take notes in his agenda book. "The bottom of every page, I started keeping a diary: this attorney fixed this case, this judge did this." Later, when everyone learned that prosecutor Terry Hake was an undercover FBI operative wearing a wire and collecting evidence on dirty lawyers and judges, Goldberg felt honored that Hake had never approached him with an offer to fix a case. Goldberg says his notekeeping, though, created an "unknown symbiotic relationship" between him and Hake: "He was fixing cases, I was documenting what he was doing." (Hake, whose book Operation Greylord: The True Story of an Untrained Undercover Agent and America's Biggest Corruption Bust was published in 2015, declined to comment for this story.)

Despite the difficulties he faced being a clean lawyer in a dirty system, Goldberg's practice eventually flourished. He bought a Gold Coast condo and a Ferrari, and in 1980 married a beautiful blond woman ten years his junior after just three months of dating. His daughter was born the next year, but he says it was an unhappy marriage. "During the night I fought her and during the days I fought the court." Goldberg says that at one point his wife and her attorney copied his lawyer's diary and turned over all the information to the IRS. The goal, he believes, was to use his financial information for leverage in the divorce, which she filed for in 1983.

Six weeks later, as he lay sleeping in his empty condo, Goldberg says he got a knock on the door. "She had taken the baby. She had taken her fur coat. She had taken everything. My mattress is on the floor," he recalls. "I look out the peephole and I see every gold badge in the United States government—FBI, DEA, IRS, Secret Service—and an assistant United States attorney." (Robert Breisblatt, who was an assistant U.S. attorney at the time, recalls showing up to the door with only two FBI agents.) Goldberg says they were all there to pressure him to testify against crooked judges after the IRS saw his notes on who was taking bribes. "They said, 'Yeah, you're the perfect witness—an honest attorney.'" But he refused.

"They said, 'We want your impressions.' I said, 'My impressions will get me killed.' I didn't help them." He claims that in retaliation the IRS audited his taxes for six years and he was threatened with arrest multiple times.

Through the late 80s and early 90s, even without Goldberg's testimony, more than 100 judges, lawyers, and court staff were indicted and convicted on federal corruption charges resulting from Operation Greylord. By that time he'd gotten close to fulfilling his law school game plan by becoming the go-to attorney for the middle managers in the organization of Mario Lloyd, one of the most notorious Chicago cocaine kingpins of the era, who'd gone from selling $1 joints to running a $30-million-a-year drug ring.

Goldberg with his son, Maximilian, and his Lamborghini in 2016 - COURTESY STUART V. GOLDBERG
  • Goldberg with his son, Maximilian, and his Lamborghini in 2016
  • Courtesy Stuart V. Goldberg

Among people familiar with Chicago's criminal circles, Goldberg now enjoys a legendary reputation, not least because he's a self-made man. Big Mo first met Goldberg in 2012 but had heard about him for many years before. "Growing up in the hood, in the city, when you see them nice cars it's what you want for yourself," Mo says of what makes Goldberg an attractive lawyer as he waits for his son's case to be called at 26th and California. "But then to meet the man behind the car or meet the man behind the myth and the legend—he was everything they said."

Goldberg had prepared to argue a motion to suppress all the evidence in Stephon's case. It was clear to him, after reading what he refers to as the "mystical code" of the police reports, that the warrantless search and seizure was done illegally and the drugs and guns—a couple of Glocks and a small, ultralightweight rifle—couldn't be pinned on Stephon.

Mo says there are plenty of lawyers who take your money but don't fight. There are also plenty who just don't have the necessary skill. Compared to them, "Goldberg's just in another league."

Over the years, Goldberg and Big Mo became friends. Mo says he believes that even if he were dead broke Goldberg would take his cases. He's been arrested for everything from weed possession to disorderly conduct to aggravated assault. Most of the time his charges were dropped or he'd plead guilty for a reduced sentence. But in 2015 Goldberg help him beat drug charges that could've landed him a 50-year prison sentence. Should he ever face federal charges, Mo is certain Goldberg would come out of retirement for him. "He's just been good to me and my family, that's all," Mo says. To him, Goldberg represents a chance "to beat the system for once. On a small scale."

Though courtroom dramas would have us believe that every criminal trial is heard by a jury, the vast majority are actually resolved by a judge in a bench trial, if they get that far. Goldberg usually prefers to take a bench trial in which he prevails against prosecutors by arguing the law. (The assistant state's attorneys used to have a "win board" in their office onto which they pinned the names and ties of prosecutors after their first jury trial victory. There was also a photo of Goldberg there, with a notice scrawled in red marker—"WARNING: Avoid at all cost!") He prefers a jury trial when the facts of the client's case are relatable and he can make an emotional appeal. If he loses the motion and Stephon's case goes to trial, Goldberg would opt for a jury because he thinks the only way he can lose is if judge Thomas V. Gainer is sympathetic to the officers whom he believes lied about where and how they found the guns.


—Kolby “Big Mo” Craig, Goldberg’s longtime client


Even if he's running late and doesn't have a long history with a defendant, Goldberg goes out of his way to make the people who retain his services feel as if they're his only clients. He makes emphatic eye contact, holds the client's hand, explains his strategy in a way that's clear and comprehensible. He never looks worried or unsure. That's because, as Mo puts it, Goldberg's already got "the blueprint" for how everything will go figured out as soon as he reads a police report. As Goldberg puts it, "I try to imagine something I want in my mind and then create the circumstances."

It's how he says he approaches life outside the courtroom too. His own biggest second chance came three and a half years ago when he met 19-year-old Miranda Carranza, an aspiring model with dark, flowing hair who was wandering around River North looking for a Jimmy John's. Goldberg was on his way to a steak dinner with clients. He had just self-published his first novel, The One and Only, about an antiques collector going after an impossible dream. "I beckoned the universe. I was the loneliest person in the world. I had everything I always wanted—but it wasn't enough."

Goldberg stopped her as she was about to pass by and they began to talk. He asked about some words in Spanish on her shirt and then asked if she knew about the five things to look for in a man—shoes, haircut, pen, tie, watch. "I wasn't really listening, I was just watching him talk," Carranza told me in early November 2016. She's from McHenry County and was on the verge of enlisting in the navy before moving to Chicago to pursue modeling instead. She says she was inexplicably drawn to Goldberg's energy. "It was the most magnetic feeling," she says, like she already knew him. He invited her to dinner. They spent the entire evening engrossed in conversation, ignoring the clients. She ate steak even though she was a vegan.

In a few months' time they were married and had a son, Maximilian Pierceson Goldberg. Carranza says at first her parents were aghast at the May-December romance. But slowly she brought them around. "I said there's nothing really you can do about it. By legal definition I'm an adult, and I'm in love with him and you're just gonna have to deal with that."

At that time—late 2016—Goldberg didn't have much of a life outside court and family. His wife, their baby son, his nephew, and his nonagenarian mother were his social world. He spent any leftover time working out at the East Bank Club (where he still entered 48 as his age on the elliptical). He read voraciously, and peppered conversation with references to Proust, Maimonides, Einstein, Nietzsche, Shakespeare, Carl Jung, W.C. Fields. He never talked about his daughter. Once, however, when discussing his own father he quoted from the Odyssey: " 'I am that father whom your boyhood lacked and suffered pain for lack of,' " then added, pensively: "I get to be a great father to Maximilian."

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In the mid-80s Goldberg was divorced and out for a good time. Business was booming, with plenty of work coming from Mario Lloyd's organization and other referrals. With a sizable disposable income, he wasn't about to get hammered and hook up with strangers at Rush Street bars like a mere mortal. Instead, he frequently hosted enormous themed parties in the nightclubs and hotel ballrooms of Lincoln Park. "That's when Oprah told me she wanted to marry me and have my baby," Goldberg recalls. A 1985 article about three eligible local bachelors in the Chicago Tribune captured the atmosphere at one of these events at the Park West, which attracted some 900 guests who paid admission:

"For this party, Goldberg had arranged for a choreographed ultra-chic fashion show, a sensuous body building routine and a karate act. Amid a cloud of smoke and a faded white light, a string of elegantly clad models struck poses with their backs to the audience. An Elvis look-alike modeled a rhinestone jacket just barely reaching his swiveling hips. In this fashion show, dance imitated life in the fast lane. An agile, blond male dressed like a penguin twirled, spun, jumped and did splits on roller skates to rock music. For the finale, Goldberg himself, keeping perfect step to the music, gyrated in a glittery silver sequined hand-sewn top."

But being the lawyer for Lloyd's street-level dealers and others implicated in drug and gun crimes wasn't all parties and high fashion. Goldberg was losing clients and clients who'd become friends to street violence on a regular basis—his "record," he says, was 12 clients dead in as many months in the mid-80s. "I would just hug people on Friday and they would be dead on Saturday or Sunday," he recalls. By far the most painful loss was that of his law clerk Michael Nevels. He was a young black man Goldberg once defended on armed robbery charges. After winning the man's case, Goldberg found him waxing his car. "He would show up and go to court with me," Goldberg says. Though Nevels didn't have any formal training in law, he offered insights from a lot of experiences as a defendant that Goldberg found useful. "He was just a sweet guy who'd never hurt anybody," Goldberg says. "But he had cases." After they'd worked together for four years, becoming close friends, Nevels died of AIDS. "Use of needles," Goldberg says. He saw Nevels the way he sees many of his clients, a perspective he would later summarize in The Snake Charmer: "No man is black or white. In the heart of the worst criminal, there's a secret garden that is within the grasp of the fresh start of a not guilty."

The years of working among so many corrupt officials and suddenly losing people he'd formed bonds with, and the painful saga of his brief marriage and protracted divorce reinforced his natural tendency to keep to himself. "It was lonely," Goldberg admits. But he never lost faith in the idea that he was doing good and necessary work. He says he's not conflicted about defending his clients, that the rush of giving someone a second chance combined with the righteous feeling of protecting citizens from government overreach keeps him going. "If I can win using the legal means that I should, I've given [clients] their fight," he says. "I didn't make this world, I only want to live in it, and I want to give them their best fight in court."

In 1990, Goldberg found himself in the defendant's seat when the feds mounted a civil asset forfeiture case in which they tried to seize his Mag Mile condo and his Porsche. The Department of Justice at the time was aggressively pursuing such cases against many drug dealers' attorneys; the government viewed their work as aiding and abetting crime and it repurposed their assets to fund the war on drugs. One of Lloyd's personal lawyers, the famed F. Lee Bailey, whose clients have included "Boston Strangler" Albert DeSalvo, Patty Hearst, and O.J. Simpson, had to forfeit $90,000 in fees from Lloyd around that same time, and many millions from other clients in the ensuing decade.

On a bulletin board assistant state’s attorneys once alerted colleagues about Goldberg’s prowess: “WARNING: AVOID AT ALL COST!” - COURTESY STUART V. GOLDBERG
  • On a bulletin board assistant state’s attorneys once alerted colleagues about Goldberg’s prowess: “WARNING: AVOID AT ALL COST!”
  • Courtesy Stuart V. Goldberg

Goldberg says the forfeiture attempt was just another one of the feds' tactics to get him to testify in Greylord cases, which were still being tried well into the 90s. Or perhaps to punish him for his resistance. In the course of the forfeiture case the prosecutors also tried to introduce evidence that Goldberg had bribed court clerks in the early 80s, but the judge denied the motion, saying these claims had nothing to do with the forfeiture case. The feds never tried to bring these charges again in a separate case, as the judge advised. During the jury trial, Lloyd testified that Goldberg carried $168,000 of his money in the Porsche. Convicted con artist and jailhouse snitch Tommy Dye also alleged that Goldberg had purchased cocaine from him and transported it in that car. But their stories were full of inconsistencies, and Goldberg's lawyer Dennis Berkson eviscerated them during cross-examinations. The jury acquitted Goldberg in 1991. As he was leaving the Dirksen federal courthouse, Goldberg recalls telling assistant U.S. attorney Mark Flessner: "Friedrich Nietzsche said, 'Whoever seeks to protect society from monsters should see to it they don't become the monster.' You and the federal government are the monster."

After that case Chicago began to feel unbearable to Goldberg. "I got so turned off with the corruption," he says. "The feds were worse than the corrupt people in the state government." He decided it was time for a change and moved to California in 1992.

His intention at first was to pass the California bar and continue practicing law. But he decided to live at the Four Seasons in Beverly Hills, where he soon met plenty of people connected to the movie business who told him he should write screenplays instead.

Though he had no previous experience or interest in creative writing, over the next six years Goldberg poured himself into screenplays, mostly on the theme of criminal law in Chicago. "I loved it so much, I never wanted to go back to law," he says. "Law is singing and writing is flying."

He says a major studio optioned several of his screenplays. He met Sylvester Stallone, Steven Seagal, and George Clooney, and says at one point or another each of them expressed interest in making a movie with him. He says that he was called in to read the script of The Fugitive based on his expertise as a Chicago lawyer. He says he pitched Oliver Stone. But none of his projects ever got the green light, and he started to suspect people were just using him for his money. "'Cause everyone was saying 'You're the greatest, I love you. Could you pay for the bill?'" When he'd ask about one of his screenplays getting made into a movie, the studio rep or actor he'd taken out for a drink or a meal would say "'Maybe next year' or 'I've got another movie I'm doing now, but you're still a great writer.' Everyone bullshitted me so much—and I have pictures with Denzel Washington, Morgan Freeman, Cuba Gooding but could never, never get a movie made."

Eventually Goldberg ran out of money and had to move out of the Four Seasons, then out of a rental apartment. He sold his car and gave up altogether, returning to Chicago. "I was in a sarcophagus. A mummy. I wasn't broke—I owed money." He moved into his sister's basement. After 18 years of practicing law and building up a formidable fortune, he'd thrown it all away on a dream.

Emerging from the stupor of this failure, he put on his last suit, borrowed $25 from his girlfriend for cab fare, and headed to the gloomy neoclassical edifice of the Cook County Criminal Court, which was still devouring casualties of the war on drugs by the thousands. People immediately recognized him in the hallways. He says he got $900 worth of business in his first ten minutes back in the building. "And I'm thinking, Schmuck, do you want to be a broke-dick writer the rest of your life? Or do you want to be a rich lawyer?"

Goldberg with nephew Matthew Kaplan and longtime client Kolby “Big Mo” Craig - COURTESY STUART V. GOLDBERG
  • Goldberg with nephew Matthew Kaplan and longtime client Kolby “Big Mo” Craig
  • Courtesy Stuart V. Goldberg

Goldberg had always avoided taking cases involving violence. No murders, rapes, child abuse, or assaults. But for the first few years of his comeback he felt that he didn't have the luxury to be choosy. In the early 2000s he represented a suburban mom who killed her adopted son and got a 12-year sentence; a drug dealer who was accused of lies that put innocent people in prison but was acquitted; and a woman who killed an infant while driving high on PCP and ultimately was sentenced to six years in prison. He is relieved he doesn't need to take such cases anymore. "I have a very powerful skill and I don't want to use it for that." He's regretted defending people who later went on to commit violent crimes. In order to be an effective advocate he needs to believe in the possibility that his clients are good people caught in a government trap; that gets harder when the alleged crimes are gruesome. "I love having my innocence," he explains. Even after all these years he says, "I still believe the clients."

Eventually, he says, he made back all his money and then some. He bought a $2 million condo on the 29th floor of a Mag Mile high-rise. In 2010 gossip columns buzzed as he was in the running to represent Lindsay Lohan; a Gawker headline read "Extremely Tan Lawyer Vows to Keep Lindsay Lohan Out of Jail With Sewing Metaphors." (He told TMZ he planned to go on the offensive: "Instead of making her reactive, like a pin cushion, [we're going] to be proactive. We're gonna go after them.") Goldberg bought Bentleys and Lamborghinis, though he began to favor the Rolls-Royce after the birth of Maximilian. (Going fast in a sports car no longer seemed worth it with a baby in the back seat.) In 2013 he was photographed for a Tribune story on local lawyers using social media to promote themselves. The next year he helped former Bears receiver David Terrell beat drug and battery charges. As he approached his 70th birthday, he was working harder than ever and had settled into a fast-paced but comfortable rhythm both in court and at home.

When talking to Goldberg one often has the impression that he's exaggerating, mythologizing, writing his own legend. It's easy to become engrossed in his stories and then to be left questioning your own credulity. When he finds a phrase that works he tends to repeat it often: "Taught school during the day, drove a cab at night." "It's a roman a clef, a novel with a key." "Nietzsche said . . . " I was astonished by how many of the phrases he uses in conversation are also in the galley of The Snake Charmer, which arrived in my mailbox last August.

I'd lost touch with Goldberg for a few months. One day he texted to say that he was planning a launch party for the novel at the Tom Ford store on Oak Street. Then he disappeared from social media, the steady stream of victorious photos with his clients halting abruptly. He no longer responded to phone calls and messages. Meanwhile, Carranza's Instagram account, on which she once proclaimed herself "Wifey to my SVG, Momma to my Maximilian," appeared with only the latter descriptor and her feed began to fill with photos and videos of the self-described homebody partying with friends.

The book is nearly 500 pages long. It's dedicated to Goldberg's nephew and son, as well as to his mother, whom he describes as a "fireball pushing me to my zenith" and who would pass away at the age of 95 in mid-January. At the center is a Chicago criminal defense attorney, Victor Raymer, who struggles to build a law practice and find love while fighting the temptation of fast money and beautiful women, the corruption of Cook County courts, and the rapacious law enforcement tactics of the federal government. Much of it closely follows the narrative of his life that Goldberg shared in interviews. While the writing is at times over-the-top, veering into melodrama and cliche, the narrative, a noirish fusion of court procedural and romance novel broken up into 90 chapters, is engaging and full of action. There are periodic interludes in which Goldberg seems to reflect not just on his characters' predicaments but on his own choices and beliefs. When describing the civil asset forfeiture case against Raymer, he writes: "All I could think about was the unbridled ability of the government to take. Not just my car. Not just my home. Something bigger and more terrible. Their ability to take whatever they wanted—to make nothing you ever achieved secure. To take your family. Your dreams. To steal your future."

When Goldberg and I finally reconnect last November, it's a little over a year since we first talked. It turned out life had thrown him several unexpected challenges in the meantime. He said his relationship with Carranza had encountered "complexities" but was reluctant to say any more.

"I would kid around—the older I got, the more Miranda appreciated me. She loved a mature man," he says. "But there is a complexity in the dynamism of having a child and having a wife that is younger." As he confronted his marital difficulties in the spring and early summer, some serious health issues (about which he didn't want to elaborate) forced Goldberg to temporarily step away from the frantic pace of his practice. Then, in August, Big Mo was killed. He was leaving a dance party in West Pullman when a gunman driving by in an SUV shot at the crowd he was in. He was only 33. The news was deeply upsetting to Goldberg.

"On a day-to-day basis I still can't believe he's dead," Goldberg says. "I just was not ready for it, and I miss him dearly." He says he'd warned Mo to be careful many times, not to go out at night or go clubbing given his criminal past. "But his lack of permanency was almost part of his character. He embraced it," Goldberg laments. "You live that life and your lack of eternity is apparent. For a while when I represented him he was a very large client. He couldn't walk down the aisles of criminal court without people saying hi to him or moving out of the way. Mostly everybody loved him."

All these abrupt and distressing changes forced Goldberg to slow down and "learn to appreciate patience and the rewards of small steps," as well as the human limitations he refers to as "primary facts." But the time away from court has also allowed him to focus on The Snake Charmer, which he hopes to finally self-publish in the near future. He still plans to have a big, glitzy release party. He's been working with an editor but hardly allowing her to change a thing. "I really liked using the phrases that I used," he says. "I told her she can't change anything. She just can look at the punctuation."

On a dark mid-December afternoon, Goldberg is sitting in his living room, a sparsely furnished white space accented by black and gold Chinese antiques that leave the sweeping views of Lake Michigan as the focal point. He's in a reflective mood. Grappling with personal challenges, he says, has allowed him to think deeply about his work in a way he hadn't in a long time. "My life was so fast-paced that I had excitement every day," he says. "Now I have to appreciate every small facet of criminal law." As he goes over clients' cases with Matthew, he's more focused than ever on the details of the police reports, imagining what he might say to the prosecutors and judges if he were in the courtroom.

While he's talking about the legal matters, the nitty-gritty elements of a case, Goldberg's scripted self seems to dissolve. Criminal law is an addiction. It's the all-body high of a not-guilty jury verdict, it's walking into a lockup of desperate people "like you're Jesus walking on water." He rejoices in people telling him "I owe you my life." He loves to see them scrawling his number on their forearms in marker. He's proud that they consider being his client a bragging right. To him, the work isn't about sticking it to the machine of mass incarceration but about snatching one person out of its jaws—saving a life, not saving the world. And his ability to do that—and to earn his lavish lifestyle in the process—has relied on his storytelling power. In front of a jury it doesn't matter what's real, it matters what you can make people believe.

Though he hasn't exactly been bored during this six-month hiatus, he says he misses "the day-to-day of being in the operating room. I want to be myself—full flare, full flavor, full steam." And he's sure he'll be back. Phone calls and get-well-soon cards from other lawyers, clerks, judges, and clients remind him of his purpose in life. Whenever Matthew—who's handling his uncle's cases in the meantime—has clients on speakerphone and they hear Goldberg in the background, Goldberg can hear relief in their voices. "I've had a few obstacles, I'm dealing with them, and clients are so happy to hear that I'm looking over their situation," he says. "They're, like, immediately comfortable and feel like I'm watching over them. They send me messages: 'We know you're a soldier, you'll be back shortly.'"

When he comes to the criminal courthouse at 26th and California, Goldberg could park for free in the garage like all the other lawyers. But for years he's preferred to rent two adjacent spots in a small lot next to the Popeye's on the northwest corner of the intersection. His luxury car is thus within easy view of the constant stream of pedestrians and traffic. If the key to being a successful trial attorney is the ability to give a compelling performance, the country's busiest criminal courthouse is Goldberg's theater. He can't wait for the day he's back onstage in front of his most loyal audience.   v

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