The Chicago defense attorney sees police officers accused of misconduct as “the ultimate underdog.”

By Maya Dukmasova

Attorney Dan Herbert LUCY HEWETT

On a crisp morning in early November, attorney Dan Herbert, dressed in a blue suit and red tie, a thick, worn manila folder in hand and a razor nick drying on his chin, strides up the steps of the Leighton Criminal Courthouse on the corner of 26th and California. Inside, his client Jason Van Dyke—who was caught on video shooting 17-year-old Laquan McDonald 16 times—stands awkwardly in line for the metal detector, his aging father by his side. Herbert dispenses cheery hellos and friendly handshakes to the sheriff’s deputies at the checkpoint. He asks that they let Van Dyke skip ahead in line and rides the elevator to the second-floor cafeteria to fill a large Styrofoam cup with black coffee. On the way to the wood-paneled courtroom where Van Dyke and his father sit demurely in a front pew and a few reporters lounge in the jury box, Herbert admits that this is his first time defending a client on murder charges. But it doesn’t seem to sway his confidence.

“Everyone thinks murder,” he says, dropping his voice in a mock terror, “but a felony case is a felony case.”

In the courtroom, Herbert continues to glad hand and banter with attorneys and court staff, greeting special prosecutor Joseph McMahon. Herbert, a 48-year-old father of four, looks like a cross between a marine and a linebacker, with a muscular build barely contained by his unpretentious off-the-rack suits, a square jaw, and a crew cut. He’s the sort of guy that a teen-movie director might cast to greet his daughter’s prom date with a baseball bat over his shoulder. He coaches Little League and is a church-going Catholic. Herbert is also a former cop, a former prosecutor, and now, the go-to defense attorney for Chicago police officers facing misconduct allegations.

In the courtroom Herbert projects a casual confidence that couldn’t be more at odds with the demeanor of his client. Van Dyke, who upon Herbert’s counsel declined to answer questions for this story, looks just barely alive: pale, with blank eyes, a puffy face, and slumped shoulders. “He’s very fragile,” Herbert tells me. “A lot of clients question me or pester me on every issue, but he’s so overwhelmed with everything else he’s happy to let me handle the legal proceedings. He’s really a nice guy—it’s amazing he’s doing as well as he’s doing.”

As the courtroom fills up with other defendants on Judge Vincent Gaughan’s call, mostly black and some Latino men, it’s not clear whether they know they’re sharing a roster with Van Dyke, who became notorious after the dash-cam video of him killing McDonald was released in November 2015. The Cook County state’s attorney’s office charged him with first-degree murder the day before the video came out—an unexpected move for an office that had for decades opted not to prosecute police officers accused of misconduct. But no one sits next to Van Dyke and his father anyway. The two remain in somber silence throughout a half-hour recess during which Gaughan takes all the attorneys into his chambers to discuss the case away from the public and press.

When they file back in, Herbert winks at Van Dyke like an encouraging coach. There’s been some progress on his fight to get McDonald’s juvenile records from DCFS, ones that would attest to the teen’s troubled childhood as a ward of the state, his being beaten, sexually abused, and in trouble with the law. This information could be relevant for what is colloquially known to lawyers as “Lynch material,” a reference to People v. Lynch, a 1984 Illinois supreme court decision that allows evidence about a victim’s past acts of violence to be used to justify killing him in self-defense. Some observers have accused Herbert of going after these records as part of a base plan to smear McDonald’s reputation before a jury. For Herbert, examining the records is a logical component of a robust defense strategy.

At the hearing, the judge sets a continuance date for December, and Herbert breezes out of the courtroom, saying good-bye to Van Dyke and stepping into an elevator with a sheriff’s deputy, who happens to be wearing a body camera.

“Jesus, they have you wearing them?” Herbert asks. The deputy explains that some new bodycams turn on automatically when a Taser is unholstered, and on the brief ride down the two commiserate about increased surveillance of police.

Out in the courthouse parking lot, Herbert throws his suit jacket in the back of his 2006 navy Lexus with a vanity plate reading “wht sox 2.” The car was probably once quite impressive, but with its worn leather interior and peeling wood detailing is now just a way to get around.

During the drive to his West Loop office, Herbert reflects on his newfound prominence in the wake of taking on Van Dyke as a client, and what it might mean for his business going forward. As prosecutors around the country have become emboldened to press charges against police officers for harming citizens, his firm is poised to be a leader in a potentially fertile area of criminal defense. Even with a new “law-and-order” presidential administration endorsed by the national Fraternal Order of Police union and other pro-cop groups, the election of the reform-minded Kim Foxx as Cook County state’s attorney in November has many local observers expecting more cases like Van Dyke’s in the years to come. Indeed, Foxx charged another Chicago cop with murder less than a month into her tenure. Nevertheless, Herbert doesn’t see himself as some kind of Johnnie Cochran for police officers.

“Honestly, I don’t think the outcome [of Van Dyke’s case] will affect my business one way or the other,” he says. “From a bottom-line standpoint, I’m already kind of at capacity anyways . . . I’m not looking to build the biggest firm in Chicago. I’m looking to just, basically, continue to provide a good defense for my clients.”

Herbert estimates that about 60 percent of his clients are cops. The rest are mostly people who’ve heard about him through grapevines that include cops. And criminal defense is only a fraction of his work. Since 2010 Herbert’s small law firm has netted as much as $600,000 annually representing police officers in administrative hearings, personal injury suits, divorce cases, and state and federal matters ranging from DUIs to civil rights charges. At times he’s also sued the police department on behalf of officers for libel, for sexual harassment, and even once for discriminating against the relatives of cops in CPD hiring. Whereas most lawyers who start their own firms tend to pick a practice area to specialize in, Herbert’s cases are united by his clientele. He’s the guy who represents cops.

But police officers aren’t just Herbert’s clients—they’re family. Not only was he once a cop, his father was a cop too, and he grew up firmly ensconced in a far-north-side Irish Catholic neighborhood full of other cops.

With activist fervor to reform or even abolish the police gaining local and national momentum since the slaying of Michael Brown in Ferguson, Missouri, in 2014, Herbert thinks police officers are now “sacrificial lambs” and the “ultimate underdog.” When he takes on a case, it’s usually because he thinks his clients have been treated unfairly. “I love representing people in that situation,” Herbert says.

This belief that he’s fighting for the little guy, combined with a lifetime of close personal relationships within the police department, breeds protectiveness, maybe even myopia. Even in his role as guard dog and guardian angel for cops, Herbert is the first to admit that there are “bad apples” among them. But he doesn’t think their conduct is symptomatic of inherent problems in policing—just shortfalls in leadership and training. And the “guys and gals” he represents? They aren’t the problem.

Herbert’s roster of clients, and his defense of them both in and out of the courtroom, suggests that he’s working hard to protect a worldview in which policing is inherently just and necessary, and cops, as a class, are the “good guys.”

But this worldview is increasingly under threat from politics, policy, public opinion, and in many cases, hard evidence to the contrary. Victims of police violence and reform advocates have for decades been calling attention to the rotten system that allows bad apples to thrive and multiply. Lawsuits that allege systemic corruption and cover-ups within the police department have cropped up every few years since the Reader’s John Conroy first exposed Jon Burge’s torture ring in 1990. And since the release of the McDonald video, the U.S. Department of Justice and a task force appointed by Mayor Rahm Emanuel have declared that misconduct is tied to a police culture in which those in charge are hesitant to jeopardize their good relationships and excessive force and racism are tolerated and go unchecked.

When someone, whether it be an activist or the U.S. attorney general, says that the police department is plagued by institutional racism, Herbert takes it as a personal insult, not a statement about the disproportionately negative effects of policing on African-American and Latino communities. And his critics say that his deep personal ties within the police ecosystem impair his ability to take corruption within the department seriously.

Herbert thinks the wide-sweeping indictments of Chicago’s policing status quo are the purview of starry-eyed children and out-of-touch suburbanites. In Herbert’s eyes, these officers aren’t bad people with bad intentions, as many believe. Rather, they’re thanklessly doing their best to protect Chicagoans from the violence that seems to be getting worse every year.

“The last thing they want to admit is that they’re scared,” Herbert says, “but they are, and I know it.” Out of that fear, he says, come the “mistakes” that land his clients in front of state or federal judges or the CPD disciplinary apparatus. But “mistakes can’t be criminalized,” he often says.

Above all, Herbert sympathizes with officers under fire because he’s been there himself.

Herbert and Van Dyke


The law firm of Daniel Q. Herbert & Associates is located in a three-story, yellow brick building squeezed between a converted factory loft and an Al’s Beef on South Jefferson. The postindustrial vibe on the outside couldn’t contrast more with the bungalow-belt-living-room atmosphere inside. Soft, well-worn couches are arrayed around a small coffee table in the waiting area. There’s always candy in a glass bowl, and sometimes even baked goods. The homey smell of drip coffee—poured in mismatched mugs culled from employees’ kitchens—permeates the air.

Herbert is keen on creating a welcoming environment. “My clients are blue-collar people,” he explains—they wouldn’t feel at ease in a cold, corporate atmosphere. “They usually have a spouse, three kids, a mortgage on their house. They are so fearful of opening up to anyone.” Even the staff helps in this regard: everyone who works for Herbert is tied to law enforcement either by blood or marriage.

Herbert didn’t always dream of being a lawyer. Growing up in a peaceful part of Rogers Park, his early ambitions were to become a police detective, like his father.

His best friend since kindergarten, John Glynn, describes young Dan Herbert as gregarious, charming, popular with girls, and a leader.

“He definitely had a presence and let you know how he felt,” Glynn says.

Herbert’s father, Michael, was a prominent figure in the neighborhood—a kind, funny, and generous man who also had a hard edge. As Glynn puts it, “You didn’t mess around with Mr. Herbert.”

Dan Herbert, the youngest of three kids, says his parents could be tough. With a chuckle, he recalls that the virtue of humility was central to life both at his Catholic schools and at home. “And that was beat into me,” he says. “[Both] by the nuns and my parents.”

In his youth Herbert also had some run-ins with cops outside the family context. “We got stopped by the police all the time, I mean, every time we went out,” he says, recalling piling into a junky Dodge Dart with his buddies to cruise around on weekends. They were also regularly busted drinking beer on the beach. “And what do you do when the police come? You run,” Herbert recalls. “We didn’t want them to take our beer; we didn’t have much money.” He didn’t always get away unscathed. When the cops caught up, “I got whacked pretty damn good.”

But one of those times the officer got so rough that, despite his fears of getting punished, Herbert told his father, who was pissed that a colleague acted this way.

“Some kid drinking at the beach—you don’t treat that person like this guy’s out doing robberies and shooting people and things like that,” Herbert says.

Herbert thinks that had he not grown up around cops, these encounters would probably have led him to have a “blanket hatred” and mistrust toward police officers. “But even at the time, I told myself, ‘OK, this guy is a moron,’ ” he says. “But never once did I think police are just assholes in general.”

Herbert graduated from Loyola Academy in 1986 and headed off that fall to study journalism, wrestle, and play football at Loras College in Dubuque, Iowa. He worked at the Board of Trade after graduating, but in 1991 he decided to follow in his father’s footsteps and apply for the police department.

“I understand that accusations are nothing more than that. I think that’s something my clients like. They realize that I’m not going to simply look at an allegation and assume that it occurred.”


Herbert’s career as a CPD officer got off to an inauspicious start. The first of the 17 misconduct allegations made against Herbert during his nine years as a cop came before he even had a chance to start off on patrol.

Responding to a crime surge, CPD rushed to hire 600 new officers in late 1991, and instead of completing full background checks on all applicants before allowing them to proceed to the academy, the department asked them to sign affidavits stating that they had no prior arrest records. The department would then continue processing the cadets’ fingerprints to confirm the information attested to.

Herbert signed such an affidavit, affirming that he’d never been arrested, taken into custody, or charged with any violation. But in May 1992, while Herbert was still in training, the delayed results of his background check came back to reveal that he had, in fact, been arrested and charged with misdemeanor battery while in his senior year of college.

The investigative documents, obtained via a Freedom of Information request, explain that the charges stemmed from an altercation with a woman outside a bar, during which Herbert allegedly “pushed her several times in the upper body and grabbed her hand hard enough to break some finger nails on her hand.” Herbert was sentenced to one year of supervision, according to the report.

The director of CPD’s personnel division accused Herbert of falsifying his affidavit; he was then investigated by the Internal Affairs Division. In a subsequent interview with the department, Herbert “admitted that he had lied on his affidavit,” the report says, but also claimed he’d told the officer who interviewed him for the job about the arrest. Ultimately the internal affairs investigator recommended that Herbert receive a 15-day suspension, but the investigator’s boss disagreed, ruling the allegations against Herbert “unfounded.”

Herbert now says the whole thing was a misunderstanding: “They were wrong about me not giving them truthful information.” He says he never lied on an affidavit or tried to conceal his arrest record, and that the arrest itself was so insignificant that he doesn’t even recall whether he told his father about it.

In the summer of 1992, Herbert began patrolling what was then CPD’s 23rd District, covering Boystown, Wrigleyville, and Uptown. The next year he was transferred to the 24th District—in his home neighborhood of Rogers Park—as part of CPD’s fledgling CAPS community policing program.

“He was a natural—he had blue blood,” says Glynn, who also briefly worked as a cop. The work can be tough on families and relationships, both financially and emotionally, Glynn says, but Herbert seemed to thrive. “I never saw any stress or tensions.”

As Herbert describes his time patrolling the streets where he grew up, one can’t help but imagine the ideal of the neighborhood cop, a kind of Officer Friendly. Intimately knowing the places and people you’re policing is “really what community policing is all about, and that’s what makes it effective,” he says. “It gave me kind of an edge in investigating and catching bad guys over there, because I knew people in the neighborhood.”

Jim Byrne was Herbert’s partner in those years, and the two were assigned to the “school car.” If police were needed at one of the district’s 30-some schools for any reason, Herbert and Byrne were dispatched. Byrne says Herbert was great with kids, and that his local street cred was always helpful.

“Anywhere you would go, everybody knew him,” Byrne recalls. “He’s like a mayor everywhere he walks into.”

Herbert’s policing experience is at stark odds with that of many of his clients today—those white cops who live in white neighborhoods in the farthest reaches of the city and patrol black and Latino communities they may know little about. Herbert says community policing like he lived it is a “wonderful concept,” but he doesn’t see how it could be extended to every part of town.

“Police officers get paid a modest salary, but if they were to live in some of the poorest and most crime-ridden neighborhoods, it wouldn’t be practical for them,” he says. “Anyone that has a family isn’t going to bring their family into Englewood to raise their kids—nothing against the people of Englewood, it’s rather against the criminals and the bullets in Englewood.”

Knowing the district and its people helped Herbert and Byrne defuse and de-escalate potentially volatile situations—the sort of situations that in recent years have turned numerous police officers into Herbert’s clients.

One time the pair were called to an elementary school where a middle-aged white man had been seen acting erratically, swinging a hatchet in front of 400 kids and saying, according to court records, “I am going to kill, kill all of you if I have to.” It’s the sort of call that “gets your blood flowing,” Herbert says.

When they arrived on the scene they found the man with the hatchet in a nearby alley. He seemed to them to be obviously homeless and probably mentally ill. Herbert says they told him to drop the hatchet, which he did. Herbert kicked it into the sewer without bothering to inventory it, and arrested the man without incident.

“This guy was not threatening. He was not going to kill any children,” Herbert says, despite the man having been heard saying just that. “He was just a homeless guy who had a knife on him, which was not unusual.”

Herbert admits that the incident could’ve had a more violent and tragic end if he and Byrne weren’t as experienced. “Could we have shot this guy?” Herbert asks. “Absolutely.”

In fact, just a few months before that, they had shot someone. On the afternoon of January 10, 1995, they received a call about a home invasion near Granville and California. They rushed to the scene, but by the time they got there, Herbert says, the suspect, a white man, had carjacked a BMW, shot the owner, and was trying to drive away.

Byrne and Herbert leaped out of their car, pulled their guns, and shot several rounds at his tires.

“We were trained to do everything not to shoot this guy first,” Herbert explains.

The suspect kept moving on flats, barely able to pick up speed, but somehow managing to merge into northbound traffic on California.

“So we were literally running next to him, trying to get him to stop, hitting him, punching him, trying to reach for the keys, telling him to ‘Stop, stop, stop,’ ” Herbert recalls.

Finally, the man crashed into a bus-stop bench on the northwest corner of Devon and California. By then several other officers had also arrived at the scene, and they surrounded the car. “He pointed a gun at us, and that’s when we all—pow! Opened up,” Herbert says. The man was wounded in the chest and leg.

Despite recalling that day in granular detail, both Herbert and Byrne say they can’t remember the suspect’s name. They say he survived, though, and was put on trial for attempted murder for pointing his gun at them. Herbert recalls testifying in the case, and says that ultimately the man was convicted. He also claims to have learned later that the man had AIDS, and that his behavior that day was intentionally reckless, although he says he can’t remember where he got this information. “He wanted the police to kill him because he didn’t have the guts to commit suicide,” Herbert says.

But some of the details of this incident as Herbert and Byrne recall them—especially the more inflammatory ones—are almost impossible to verify. The only news account of the shooting, from the Chicago Tribune, didn’t name the suspect (or the officers, for that matter) and was based on information provided by a police spokesman. The Reader made numerous public records requests with CPD, the clerk of the Circuit Court of Cook County, and the Illinois Department of Corrections in an attempt to identify the man and corroborate the story. But CPD didn’t archive use-of-force reports from the 90s, the man doesn’t appear to have filed a complaint against Herbert or Byrne, and none of the nearly 200 men still serving time in Illinois prisons for crimes committed in 1995 were arrested near the time of the shooting or charged with felonies that could have stemmed from this incident. And without the man’s name, other public records, such as arrest reports or legal case files, can’t be requested or found.

Herbert received a distinguished service award from the Fraternal Order of Police for his efforts in apprehending the man that day. He says this incident was the only time he discharged his weapon in nearly a decade on the force. And he still stands by his actions.

“That was a very good shooting.” he says. “I’ve used force on a lot of people, but I like to think that I always, always used force in the appropriate manner: to defend myself or somebody else.”

Byrne agrees with Herbert’s depiction of his time as a cop, saying that his former partner was always level-headed and used good judgment on the job: “I knew I was safe with him all the time. He wouldn’t walk into things charged up crazy.”

But some of the misconduct allegations against Herbert, which the Reader received from CPD along with the file regarding his arrest record, paint Herbert as the sort of cop who could also get rough.

Some of the allegations are trivial: Herbert and Byrne were once accused of singing Spanish songs from the intercom of their car. The complaint wasn’t sustained, and Herbert says it wasn’t unusual to receive such “bizarre” complaints.

But seven of the reports against Herbert during his nine years with CPD allege excessive use of force. Although none were sustained—not unusual given that IPRA’s precursor, the Office of Professional Standards, sustained fewer than 10 percent of misconduct allegations in the 90s—one alleges that the victim, a 15-year-old black boy, was on his way home from school when Herbert and Byrne stopped and arrested him for trespassing. The boy claimed that one of them slapped and verbally abused him in the car and the other, once they arrived at the 24th District station, slapped him with some rolled-up papers and “passed gas” in his face.

Five use-of-force complaints allege Herbert shoving, slapping, kicking, or punching black men, and once calling a man he detained the N-word. In March 1996, a 26-year-old black man who’d been arrested for theft at a Rogers Park pawn shop alleged that the arresting officer handcuffed him to a wall of an interview room and questioned him about “previous complaints he had made against a member of the police department.”

At that point Herbert allegedly arrived, recognized the arrestee, and asked the arresting officer: “Do you mind if I get physical with him?” Herbert was left alone in the room with the arrestee, allegedly stretched, said he was “ready for a workout,” and slapped the arrestee, punched him in the stomach and chest, and attempted to kick him in the groin.

Herbert denied all the allegations at the time of the investigation, and so did all the other officers named in the complaint. The investigator ruled the allegation “not sustained” and concluded: “[Victim] related that no one witnessed the alleged physical abuse, as it occurred in a closed room. Also [victim] did not seek medical treatment to substantiate his claims.”

Herbert still maintains that none of what the man alleged occurred. But the experience of being confronted with these allegations fuels his ability to build rapport and trust with his clients—he knows both what it’s like to use force and to be accused of using it improperly.

“I understand that accusations are nothing more than that,” Herbert says. “I think that’s something my clients like. They realize that I’m not going to simply look at an allegation and assume that it occurred.”

Old picture of police officers

Herbert, left, with his former partner Mike Conway, at a friend’s engagement party circa 1993.

Over the last few years Herbert has represented officers charged with the sexual assault of an inebriated woman, officers who have allegedly beaten up shoplifting teens, officers involved in domestic violence, and officers accused of planting evidence, perjury, and DUIs. He represented two officers involved in covering up the killing of David Koschman by former mayor Richard M. Daley’s nephew Richard Vanecko. He’s also represented black officers suing the city for discrimination and a female officer suing her boss for sexual harassment.

He regrets taking on some cases, but usually only because a client wound up being difficult to work with. Just about the only cops Herbert doesn’t want to defend are alleged child molesters. In November, he was glad when a CPD officer facing federal sex-trafficking charges involving a child went with another lawyer.

“In order for me to be good, I kind of have to believe in the cause, and believe in my client,” Herbert says.

The difference between a cop accused of paying to have sex with a 14-year-old girl and one accused of murder?

“I know what was going on in my client’s head in these shootings,” he explains. “There’s no malice whatsoever in these individuals.”

But the cases that have catapulted Herbert to prominence haven’t only been instances of potentially egregious uses of force, they’ve also been ones with racist overtones: Jason Van Dyke shooting Laquan McDonald; Marco Proano emptying his gun into a car full of unarmed black teens; and Timothy McDermott, who in 2002 posed for a scandalous photo with a black arrestee.

In the infamous “hunting” photo, McDermott and officer Jerome Finnigan, both of whom are white, pose kneeling with rifles next to a black man—later identified as 18-year-old Michael Spann—prone on the floor with tongue out, eyes rolled up, and deer antlers taped to his head. The photo was widely cited as yet another indicator of CPD’s deep-rooted racism, and fit into a long history of debasing and dehumanizing photographs of African-Americans created by white supremacists for fun.

At the time the photo was taken, both officers were part of CPD’s infamous Special Operations Section, whose members, according to civil litigation records and criminal investigatio