Crime law security service officer cop


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 news.

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 imnewsive, 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 news 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.


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.”

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 investigations, beat, harassed, robbed, and kidnapped citizens. In 2011, Finnigan, the most notorious member of squad, was sentenced to 12 years in federal prison for ordering a hit on a fellow officer, among other crimes. McDermott, however, was never charged with any wrongdoing, and was a detective when the photo surfaced and the department moved to fire him. Herbert represented him in administrative hearings and appeals.

Though they ultimately lost, Herbert says he still believes his client deserved to be a cop. McDermott, Herbert says, is “an extremely good man.” And in his eyes the photo was nothing more than a moment of poor judgment by a young officer trying to fit in.

No matter how “horrible” the photo might seem, Herbert insists, his having posed for it doesn’t mean that McDermott is racist or hates black people.

“It was the opposite—none of that was a factor,” Herbert says. “Mistakes can’t be criminalized. I sympathize with these people that make mistakes and having it held over their head. And Tim McDermott—that was exactly what it was.”

Statements like these are a testament to Herbert’s core belief in the fundamental goodness of people in law enforcement—but also to the mental gymnastics he’ll perform to arrive at the most charitable interpretations of their actions.

In an early conversation about the photo, Herbert argued that the picture didn’t tell the full story of what might have happened between Finnigan, McDermott, and Spann. He advanced the idea that perhaps Spann was a friend of the officers, and that the three were simply goofing around. “Everyone is assuming that [Spann] was an arrestee,” he said. “I don’t know why. Because he was black?

“We’re talking about people’s careers here,” Herbert continued. “And when we’re tagging them with the horrible tag of being a racist, we better have our facts in order.”

But the identity of the man in the photo was revealed by the Sun-Times in 2015, only a month after the image was made public. McDermott and his partner had arrested Spann, then an 18-year-old high school student, two days before Christmas 2002. The officers claimed they arrested Spann for selling weed on the street, but Spann’s uncle, who was arrested with him and witnessed the photo shoot at the station, told reporters that the cops had raided his home without a warrant—something Special Operations Section officers were frequently accused of doing.

When I brought this up with Herbert, he remained unconvinced that Spann was the man in the hunting photo, and insisted that the information provided by the Sun-Times was never part of the city’s case against McDermott. He said CPD wasn’t able to provide any arrest report to identify Spann during McDermott’s hearings.

Spann, who was killed in a drive-by shooting in 2007, isn’t able to speak for himself. But his uncle told the Sun-Times that he remembers how terrified his nephew was that night and that the officers “were all laughing, telling him to crawl around, stick his tongue out.”

But, Herbert said, if it were true that the man in the photo was an arrestee, “I think it would change my opinion about the incident.” If that man was really an arrestee, Herbert said, then McDermott’s behavior would be “absolutely incorrect.” He’d go as far as to call it racist.

Herbert represented CPD detective Timothy McDermott, right, after a 2002 photo surfaced showing McDermott posing with fellow officer Jerome Finnigan, left, and a black arrestee later identified as 18-year-old Michael Spann. The photo was widely cited as an example of CPD’s deep-rooted racism. COURT FILE

Over several months of reporting, Herbert and I had extensive conversations about race and racism in policing. Most of them took place in his man cave of an office. As we talked he’d recline in a wide chair behind a desk scattered with disheveled legal pads, manila folders, a mini replica of Comiskey Park, and a business-card holder shaped like a baseball mitt. The exposed brick walls are covered with more White Sox memorabilia, degrees, awards, newspaper articles made into plaques, and family photos.

Throughout these relaxed and meandering talks it became apparent that Herbert’s conception of racism doesn’t extend beyond personal animus.

“Are there racists in the police department? I’m sure there are, just like there are in any profession,” he says. “But certainly it’s not a systemic problem where the majority of police officers are racists, by any stretch.”

Herbert remains perplexed by the argument that policing, as it currently exists, is institutionally or structurally racist. He seems unwilling or unable to grasp that regardless of the individual motivations of the workers within the criminal justice system, what makes the establishment racist is that black and brown people get disproportionately mistreated and killed—and that this form of racism is as significant as anyone’s personal malice.

Herbert recalls how angry he and other people in the police community felt when the mayor’s Police Accountability Task Force released its report last April citing institutional racism in the police department. “CPD’s own data gives validity to the widely held belief the police have no regard for the sanctity of life when it comes to people of color,” the report read.

“The way I took it, and the way a lot of people took it, is, well, [Police Accountability Task Force chair Lori Lightfoot] just called my dad a racist,” Herbert says. “And I don’t know what her definition of institutional racism is, because I don’t think she explained it.”

And yet, when Herbert decided to defend Van Dyke, his 16-year-old daughter was furious.

“She believes in her heart of hearts that police mistreat minorities,” Herbert says. “And when I took this case, she thought what the rest of the public thought—that this was just a horrible example of police abusing their authority, especially with respect to minority communities, black communities.”

On the contrary Herbert argues that the reason there are so many black people caught up in the criminal justice system isn’t because of their race, but because they come from neighborhoods with higher rates of poverty and therefore higher crime rates. He adds that the reason such neighborhoods in Chicago are disproportionately African-American is because black people have disproportionately suffered at the hands of politicians and under harmful policies, such as the destruction of public housing and school closures.

Police, he says, stand at the end of a long chain of government intercessions in people’s lives. And he believes they are unfairly taken to task for bias against African-Americans when the real discrimination is perpetrated by politicians and policy makers at other levels of the state.

“Nobody looks at the politicians to say, ‘Well, did you make the right decision in closing this housing project or closing this school? And did you do enough to make sure DCFS was properly protecting them?’ ” Herbert says.

In a way, Herbert’s right—his assessment of the roots of institutionalized black poverty and criminalization squares with well-established historical facts. But of course, black Chicagoans have been complaining about these types of discrimination and pointing to these root causes of crime for decades, and have been pleading—especially since the murder rate started spiking again in 2012—for the city to invest in their neighborhoods and fight segregation, not just hire more cops.

And yet, as we talked, Herbert seemed to be mulling over, for the first time perhaps, that maybe what makes, say, school closures racist isn’t that the people who made the decision might personally hate black people but that, overwhelmingly, it’s black children who suffered—that what makes it racist isn’t the intention, but the impact.

“I can completely understand people that are on the receiving end of those decisions thinking that it’s racist,” he eventually said, leaning back in his chair after a long pause. “You could certainly argue that certain policies or institutions have effects on minority communities that may be considered institutional racism. But again, when I think of it, it goes back to—for the most part people are not motivated by the color of somebody’s skin . . . It’s more about other factors, if that makes any sense.”

After another pause he concluded with a platitude that seemed to be aimed as much at himself as at me: “It’s important that everyone see the perspective of the other side, and that’s not what we’re doing now. And you know what? It’s a very hard thing to do.”

“I am sinking in my fucking seat. I have a lawyer that I knew in that moment was an enemy.”


Though Herbert has never lost his faith in the righteousness and necessity of policing, his faith in CPD has wavered over the years. Between 1993 and 1995 he took one promotional exam for detective and one for sergeant, but never made it. And, he says, no one would explain to him what he did wrong.

“When I saw the promotional system, that’s probably the biggest reason that spurred me on to think about a life outside the police department,” he says.

The DOJ report on CPD released in January cited a persistent lack of fairness and transparency in the department’s promotional system dating back to the 1990s. Herbert says the DOJ “addressed everything I was saying to my crew of friends 20-something years ago.”

Herbert believes that promotion was then based on having the right connections more than on merit. And though his father was a decorated and well-respected detective, Herbert says he wasn’t the connected type.

“I was the son of a cop that was not somebody who was involved in the political structure of the police department,” Herbert says. “My dad never asked for a favor.”

And so, after his shifts on patrol, Herbert worked on a master’s degree in criminal justice at Lewis University and then began law classes at DePaul. He eventually left the streets to teach at the police academy, but stayed on the force until he completed his law degree in 2001. Herbert applied for a job with the Cook County state’s attorney’s office immediately after graduating.

Herbert’s father served as a bodyguard to Dick Devine, head of the state’s attorney’s office at the time, and he became a role model for Herbert.

Devine says he was happy when Herbert, whom he’d watched grow up, decided to become a prosecutor. He seemed to have the right temperament. “I saw him as just a very classy young man—he was competitive, he was involved in a lot of sports,” Devine says. “My sense of Dan was he was very confident in himself and had a strong personality.”

Devine didn’t have many occasions to interact with Herbert as a rookie prosecutor, but says he heard only good things about Herbert’s performance from his supervisors, and that the work of a prosecutor “looked, not surprisingly, like a very good fit for Dan.”

Though Herbert was only with the state’s attorney’s office for three and a half years, he managed to make it all the way to a felony courtroom—a rarity given that most new prosecutors spend many years working misdemeanors and rotating assignments throughout the county before getting assigned to a stable position in one courtroom. As third chair in a felony courtroom in suburban Markham, Herbert helped prosecute a variety of crimes. Here, he says, as when he was a police officer, what made the job rewarding to him was putting away the bad guys.

Soon, though, a new opportunity presented itself. In 2004 a representative from the Fraternal Order of Police Lodge 7 approached him with an offer to be the local police union’s in-house counsel. His colleagues urged Herbert to take the job. “This is what you love doing, you love representing the police,” he recalls them saying. By that point he had two kids, so bumping up his salary from around $50,000 to $80,000 seemed especially appealing.

Herbert was the in-house attorney at the FOP for five years. “It was a big learning curve,” he says, due to the variety of legal work beyond his expertise in criminal law.

Over time Herbert learned that union leadership and members weren’t happy with the FOP’s outside law firm. He thought he could do a better job, and in 2010 decided to open up a new practice to serve the union’s needs. In the first two years of business, his firm made more than $1.25 million in legal fees from the union, according to the FOP’s public tax records.

In those early years, FOP referrals made up the bulk of Herbert’s business, and he was frequently called to represent officers interviewed by IPRA or CPD’s Internal Affairs Division about alleged wrongdoing on or off duty. The practices of FOP representatives and lawyers around police misconduct were also addressed by the DOJ report. One of the difficulties with investigating misconduct allegations, the report explained, is that the same union lawyers often represent the officers accused of misconduct and officers who witnessed the incident. Thus, the lawyers facilitate a free flow of information that could contaminate officers’ testimony or lead to collusion. “Witness coaching by union attorneys is prevalent and unimpeded,” the report notes.

Herbert maintains that most of the problems described by the DOJ report don’t apply to the way he works, and that the specific incidents the DOJ cited as examples of troubling behavior by union attorneys happened precisely at the moment when he had a major falling out with the FOP.

In March 2014, then-president Michael K. Shields dropped Herbert as the union’s preferred contractor. Shields accused Herbert of double billing the union, an allegation that “infuriated” Herbert. He says this was just an excuse to oust him. Though he wouldn’t get into specifics, he says that he “didn’t really agree with the ethics and morality of the people who were running the union,” and let his opposition be known.

So when he was fired, Herbert says it wasn’t a surprise, but he admits that he was “kind of immature about it,” adding, “when you lose a big chunk of business in one day and you’ve got four kids . . . ”

Shields claimed in court documents that Herbert responded to the news by sending “insulting and provocative” phone and e-mail messages, calling him a “cunt,” and finally, showing up at his house drunk and threatening to kill him and his family.

“He alleged that I was stealing,” Herbert explains. “I went over there to tell him, ‘You better not do that.’ And, yeah, I got heated and, yeah, I told him I was going to kick the shit out of him. But the part about threatening his family is completely false.” Herbert also denies that he was drunk that night.

Shields took out a restraining order against Herbert, and the FOP sued Herbert to get their members’ records from his office. Herbert admits that he refused to give them back until the union settled its outstanding bills, which eventually it did, and the lawsuit was dropped.

“I was scared that these guys were going to dirty up my reputation,” Herbert says now, reflecting on the incident. Losing the FOP’s business seemed like losing his job, not just a client. “It was a tough thing to swallow because I really thought, ‘This is going to kill my legal career.’ ”

Despite the financial hit, Herbert says losing the FOP as a client was the greatest thing that ever happened to him, “because I focused on other areas of law and other clients and my business flourished.”

Beginning in 2012 Herbert had a number of big wins, including $375,000 in a defamation suit by members of an electrical workers’ union and $500,000 in a personal injury suit; he also convinced a judge to supnews evidence of five kilos of cocaine seized from a client in an unlawful search.

In that period he also continued to represent officers who came to him independently of the FOP. One such officer was whistle-blower Shannon Spalding, who in 2012 sued the police department’s top brass. As was recently detailed by Invisible Institute reporter Jamie Kalven in a series of stories for the Intercept, Spalding and her partner, Danny Echeverria, worked undercover with the FBI, investigating how top-level cops were covering for an extensive drug ring run by subordinate officers. But eventually their cover was blown, and colleagues and bosses within the department began to retaliate against them. They thought a lawsuit would protect them.

Spalding, who is no longer on the force and devotes her time to police accountability and transparency efforts, says she had reservations about approaching Herbert. She thought he might have previously represented or personally known some of the people she wanted to name in her lawsuit, and she worried about conflicts of interest.

“I told him, ‘You may know these bosses; I don’t know if you can represent me.’ ”

According to Spalding, Herbert acknowledged that he knew some of the people she wanted to sue, and a few days after their first meeting told her he wouldn’t take the case in order to avoid potential conflicts. He instead recommended another attorney, Patrick J. Walsh. Walsh eagerly accepted, and Spalding says she trusted Herbert’s recommendation.

On November 1, 2012, the day they were set to file and announce the suit to the media, Spalding says she got a call from Walsh.

“He says, ‘I have some great news: Dan Herbert has decided to join the case and be cocounsel.’ ”

Spalding was in shock. “We go down there, and Patrick Walsh and Dan Herbert have already set up the payment split and the contract and everything without even consulting my partner and I,” she says. “We’re like, ‘Wait a minute, how can Dan Herbert do this? I thought this was a conflict?’ We never got the answer to that question.”

Both Herbert and Walsh dispute Spalding’s account of these events, saying that they worked on the case together from the start—although Herbert says he had a large caseload at the time and relied on Walsh to do most of the heavy lifting, and Walsh says he did most of the legwork due to his experience with federal discrimination suits.

“If I had a conflict, I wouldn’t have taken it,” Herbert says.

Despite her initial concerns, Spalding says that amid the flurry of media attention, Herbert told her that she didn’t need to worry—he had thought it through and he would be an asset for her case.

“He said, ‘I’m 100 percent for you, but I am like your secret weapon,’ ” Spalding recalls. “ ’I can get information from people I know in the department that we can then turn around and use to your benefit . . . It’s gonna be the biggest case ever—I definitely want my name attached to this.’ ” Herbert says he doesn’t recall saying this, but allows that his knowledge of the department’s people and policies is often an asset for his clients.

Spalding says the whole thing seemed strange, but that she had bigger worries. “I’m terrified,” she explains of her mind-set at the time. “I have to go into work with the bosses that I just announced on TV are corrupt.”

During the months after Spalding and Echeverria filed their lawsuit, they say the retaliation against them escalated. They were threatened by colleagues and supervisors on a daily basis, and assigned to dead-end cases or dangerous ones with no backup. “I felt like they were setting us up to get hurt,” she says.

Things came to a head in April 2013, when police internal affairs sergeant Mike Barz detained Spalding and told her that federal eavesdropping charges would be filed against her if she didn’t drop her suit. Spalding told the Reader, the Intercept, and testified in a deposition that Barz and another sergeant ushered her into a tiny room at CPD’s Homan Square facility. On the way, she yelled to Echeverria to call their lawyers.

Once the door was closed, Echeverria says he placed at least a dozen calls and text messages to Herbert and Walsh with no answer. “It was nerve-wracking because it was my partner going through something and I couldn’t be of any help,” he says.

Meanwhile, inside the room, Spalding says Barz questioned and intimidated her for some 45 minutes. The experience brought Spalding to a “breaking point.” Eventually she was in tears.

“I knew they were about to put a false case on me,” she says. “In that instant, I knew the power the police department has to make people look guilty.”

Then Barz’s phone rang. It was Herbert.

As Spalding later testified in the deposition, the room was so small that she could hear the conversation on both sides of the line.

She remembers Herbert’s cheery voice. “I hear, ‘Hey buddy, how are you? What’s going on?’ ”

The two made small talk, and Barz asked Herbert whether he’d make it to an upcoming gathering. “You’re my best friend, buddy,” Spalding says she heard her lawyer say to the man detaining her. “I wouldn’t miss it for the world.”

“I am sinking in my fucking seat,” she recalls. “I have a lawyer that I knew in that moment was an enemy.”

Eventually Barz told Herbert that he had Spalding.

“Dan says: ‘You don’t really have shit on her, do you?’ ” She heard Herbert tell Barz that he’d need to let her go. She recalls Barz responding: “I’ll make this disappear, but you have to promise me that you do not make me part of this lawsuit.”

Herbert says he doesn’t recall this conversation with Barz, but confirms knowing Barz and having “a lot of friends in common.” He also challenges Spalding’s claim that Barz would have leveraged charges against her in exchange for not being in her lawsuit, describing him as a “by-the-book guy.”

Barz, meanwhile, denies or challenges Spalding’s account of these events, insisting that he never detained her, that the conversation actually happened in her office, and that it lasted just 15 minutes. He remembers speaking to Herbert during the encounter, but says they had no personal relationship and couldn’t have discussed a friendly get-together. He denies offering Herbert a quid pro quo.

“To suggest that I was involved in some kind of shenanigans with Dan Herbert is an absolute lie and it’s an attack on his credibility and mine,” Barz says.

Eventually Spalding was released. She knew she’d need a new lawyer as soon as possible and took her case to Smith, Johnson & Antholt. She never saw or spoke to Herbert again.

Herbert remembers Walsh calling him to tell him Spalding had taken her case elsewhere, but not the reason why.

“I’m like, ‘Good,’ ” he remembers saying. “I know they were driving Pat nuts, so I felt bad that I brought Pat into it. They were difficult clients.” (Walsh declined to comment on what Spalding and Echeverria were like to work with.)

Spalding became convinced that Herbert got involved in her lawsuit in order to undermine it. When Herbert and Walsh filed her complaint in November 2012, “they wrote it so weak that the defense could win the case,” Spalding says she realized after getting a new lawyer. “If it had remained the way it was, I wouldn’t have won anything.”

She knew that Herbert was on the outs with the FOP at the time, and now thinks that his true goal was to steer her litigation in such a way that she and Echeverria would lose and their bosses would be vindicated.

“It’s completely meritless and it makes no sense from a logical standpoint,” Herbert says of this allegation. “There’s no way that that lawsuit could have affected my relationship with FOP in any way.”

In May of last year, shortly before Rahm Emanuel was supposed to testify in the suit, the city settled with her and Echeverria for $2 million.

Spalding says that she hopes her experience with Herbert will serve as a cautionary tale for other Chicago police officers who might not think twice when the union guides them to Herbert’s door. While Herbert could be doing a great job for some clients, Spalding thinks it’s only as long as the clients’ interests aren’t in conflict with the city’s. After all of her experiences, she’s sure that, despite outward adversarial appearances, Chicago’s top politicians, the FOP leaders, and CPD’s top brass are all playing on the same team. And she’s convinced that Herbert is there to make sure they win when they need to.

“He blows with the wind,” Spalding says. “Whatever the city wants will dictate how Dan Herbert represents you.”

Herbert’s homey office in the West Loop feels more like a man cave. He says his clients are “blue-collar people” who wouldn’t be at ease in a cold, corporate atmosphere. LUCY HEWETT

By the end of 2013, the FOP leadership that fired Herbert was itself on the way out. Shields was removed as president after, among other things, he accused negotiators of fixing police contracts with the city through back-room deals.

Current president Dean Angelo Sr. was elected in April 2014, and Herbert was quickly restored as the FOP’s preferred contractor.

“We were anxious to bring Dan back into the fold,” says Angelo, who first met Herbert when the two were working on their master’s degrees at Lewis University. “Knowing Dan, knowing his dad—to me there’s a major trust factor there.”

Herbert says he was glad to be back, but that he made it clear he wouldn’t stand for any more accusations of theft or impropriety. Since then, he says things have been running smoothly, adding that Angelo and his team are “gentlemen” in the way they do business. He estimates that about 45 percent of his work now comes from FOP referrals.

Herbert’s tenaciousness in the courtroom, his comfort going to trial, and the way he publicly champions his clients have earned him respect and confidence. Even when Herbert loses cases, his reputation and his business don’t seem to suffer. Though some people grumble about him in anonymous online venues such as the Second City Cop blog, his wholehearted devotion to police officers seems rarely to be questioned.

Aldo Brown, a black former police officer convicted on excessive force charges for beating a south-side convenience store clerk and currently serving two years in federal prison, says he was happy with Herbert’s representation and commitment to the case. It didn’t faze him that Herbert wasn’t necessarily the premier expert on federal criminal defense.

“There’s always the question, because I ended up in prison—could I have made a better decision [about a lawyer]?” he muses. But then again, he’s also met plenty of inmates who spent many thousands of dollars hiring the best federal criminal defense experts and still ended up right where he is. “I think Dan did do an exceptional job given that I only got sentenced to two years and not longer,” Brown says.

Herbert is currently shepherding Brown’s case through appeal.

I heard similar appraisals of Herbert’s dedication and professionalism from other clients, including Proano—currently facing federal criminal charges—and James Horn, a former Glenview cop recently acquitted on perjury charges.

But it’s Van Dyke who will keep Herbert in the spotlight for many months to come. If his client beats the charges of first-degree murder and official misconduct, Herbert is sure to be seen as a miracle worker. For now, he’s trying not to think too far ahead. “At the end of the day I’m just a guy out here with a small law practice doing the best I can to help my clients and help my family,” he says.

At a hearing on the Van Dyke case in early February, Herbert is radiating energy. He paces around the courtroom, makes small talk with Van Dyke and his father, and greets various lawyers there on other matters.

While Van Dyke, slumped in a pew, silently mouths prayers, Herbert files new motions to dismiss the murder charges that will likely keep the case from going to trial before the end of 2017. One claims that Van Dyke’s rights were violated under statutes that protect public employees from prosecution if they give incriminating statements during investigations by their employers. The other argues that the Cook County state’s attorney’s office improperly instructed the grand jury while hustling to charge Van Dyke before the release of the video.

Many criminal defense attorneys are motivated by their love for the legal chess game. Others have a principled dedication to the notion that everyone, even people accused of commiting horrific crimes, deserves equal protection under the law. But Herbert seems principally fueled by the belief that his clients are innocent, respectable, hard-working people scapegoated in today’s political climate. He sees their persecution as dangerous to the social order and defending their honor as a matter of his.

“There was a rush to sacrifice Jason Van Dyke to the angry mob that was out there,” Herbert says firmly to Judge Gaughan. As usual, he argues, it was the lowly officer who was forced to take the fall as politicians scrambled to save themselves. If people want the police to act differently, Herbert believes they should lobby Springfield to change state laws that regulate cops’ use of force, and then take CPD to task on how well it trains its officers, instead of placing the blame at the feet of cops like Van Dyke.

“The shooting,” he concluded, “was justified.”  v

Correction: An earlier version of this story mistakenly identified the agency that conducted the investigation of Dan Herbert’s arrest record. It was CPD’s Internal Affairs Division, not the Office of Professional Standards.