Special prosecutor Joseph McMahon, from left, attorney Daniel Herbert and Herbert’s client Chicago police Officer Jason Van Dyke during a hearing on the shooting death of Laquan McDonald at the Leighton Criminal Court Building on Aug. 17, 2018. (Antonio Perez/Chicago Tribune)

By: Megan Crepeau and Jason Meisner | Contact Reporters
Chicago Tribune

Attorney Daniel Herbert was minutes into arguing that the murder charges against Chicago police Officer Jason Van Dyke should be thrown out when his tone took on more urgency.

The shooting of teen Laquan McDonald 16 times was “business as usual,” Herbert declared in court, accusing prosecutors of failing to explain to grand jurors that state law allows officers to use deadly force on such a knife-wielding individual.

He strode from behind the lectern, waving papers in the air, his voice rising in indignation. The pace of his words quickened. A slight Chicago accent emerged.

“Not only can you shoot ’em, it’s your duty to shoot ’em!” Herbert shouted. “You have to prevent the escape of this dangerous armed citizen.”

Moments later, Joseph McMahon, the Kane County state’s attorney appointed as special prosecutor in McDonald’s killing, stepped behind the lectern, arguing in restrained tones that Herbert’s accusations had no merit.

He dryly cited case law, provided detailed summaries of Illinois statute, even gave a brief history of the role of the grand jury in the American justice system.

Now, months later, as Van Dyke nears trial on a national stage, the spotlight will shine on the two very different lead attorneys: one loud, the other soft-spoken; one spontaneous, the other academic.

Herbert could not be more Chicago. The 50-year-old still gives the imnewsion at times of his old days as an inside linebacker with his broad shoulders stretching his suit jackets and his hair buzzed in a perpetual drill-sergeant crew cut.

A former Chicago cop and Cook County prosecutor, he’s well-versed in the myriad quirks of the Leighton Criminal Court Building at 26th Street and California Avenue, where Van Dyke is slated to stand trial beginning Wednesday.

In court, he’s animated, talks with his hands and often walks around without using a lectern or looking at notes.

Since going into private practice, Herbert has carved out a niche as a go-to lawyer for police officers accused of wrongdoing. Though he has handled several high-profile police misconduct cases in recent years, Van Dyke’s trial marks his first defense of murder charges.

“What you see is what you get with Dan,” said Dick Devine, the former Cook County state’s attorney who has known the Herbert family for decades. “He’s very solid and straightforward. He works hard and has good common sense.”

By contrast, McMahon is very much an outsider — indeed, he was chosen for his outsider status — at a courthouse notorious for its clubbiness. He is a former partner in an elite law firm who has served for the past eight years as Kane County’s top prosecutor. He has handled plenty of murder trials and prosecuted several police officers for wrongdoing, but none compare with the high profile of this one.

Special prosecutor Joseph McMahon, the Kane County state’s attorney, speaks out at the Leighton Criminal Court Building on Aug. 15, 2018, during a hearing for the shooting death of Laquan McDonald. (Antonio Perez/Chicago Tribune)

Hailing from a small town north of Elgin, McMahon, 52, is known for his methodical and detailed approach. He speaks calmly in court, in a pitch that sometimes seems near monotone. He married his high school sweetheart, runs Iron Man triathlons and even golfs with the same even-keeled demeanor that he brings to his cases, friends and colleagues said.

Growing up, McMahon earned the nickname “Captain Joe” — the guy in the group who was always looking out to make sure things didn’t get out of hand. His friends said he’s carried that same sense of responsibility throughout his career.

Veteran attorney Terry Ekl, who has known McMahon for years, said he expects the veteran prosecutor to put on a very organized, workmanlike case against Van Dyke in spite of the hoopla surrounding the trial.

“I don’t think it’s going to be anything cute,” Ekl said. “Boy Scout, that’s the way I would describe him. … I don’t mean that derogatorily. He’s just a straight shooter.”

While it’s clear that both lawyers are taking their roles seriously, they’ve sometimes gone about it in different ways. Herbert has frequently sparred with the judge over evidence and other issues, while McMahon has taken a less combative approach.

Herbert said that the case has already taken a toll on his family life, particularly in the months after Van Dyke was charged when he was bombarded by media calls and found it difficult to focus on anything else.

“I was short with my family, I was short with clients, I was short with the kids that I coached,” Herbert said. “I’ve since kind of been able to come to grips with it, and I’ve been much better.”

In recent weeks, as the judge was newsing both sides to work out last-minute details and holding almost daily hearings, Herbert took off on a preplanned, weeklong vacation with his son to the Baseball Hall of Fame in Cooperstown, N.Y.

McMahon, meanwhile, told a Tribune reporter he might be unavailable for follow-up questions after his interview because he’d be hunkered down, preparing for the trial.

‘Don’t go near it’

When Herbert first saw the police dashboard camera video of the McDonald shooting, he knew it looked bad.

It was the morning after the October 2014 incident. Herbert was sitting with a group of detectives at the Area Central police headquarters after being called in by the Fraternal Order of Police to represent the interests of Van Dyke and other officers who were at the shooting scene.

“I’m sitting down and everyone is standing over me, and we’re watching it. And I remember looking at the shots at the end, and I’m like, ‘Oooh, that’s not good, guys,’ ” Herbert said in a recent interview at his West Loop law office. “And they’re arguing with me, ‘Ah, you know, he’s still holding the knife.’ I’m like, ‘I don’t know, I gotta find out what was going through (Van Dyke’s) mind at the time.’ ”

Herbert said once he met Van Dyke and got the “full story” from him, he knew he’d “represent the guy in a heartbeat.”

Van Dyke, he said, struck him as a mild-mannered, simple guy who had never made waves in his career. He had no previous shootings in his background despite working some of the city’s most dangerous areas. Most important, Van Dyke was well-liked by his fellow officers.

“To me that’s a big deal,” Herbert said. “The good policemen know the bad policemen better than anyone.”

Attorney Daniel Herbert, far right, a former Chicago cop and Cook County prosecutor, addresses the court during a hearing for the murder trial of his client, Chicago police Officer Jason Van Dyke, at the Leighton Criminal Court Building on Aug. 7, 2018, in Chicago. (John J. Kim/Chicago Tribune)

Out in Kane County, McMahon saw the now-infamous video like most people did — after a court ordered its release in November 2015. It was hard to ignore the firestorm the recording unleashed, McMahon said, but he did not follow the story closely or form a strong opinion about the charges faced by Van Dyke.

The next year, when then-State’s Attorney Anita Alvarez withdrew from the case after months of protests and political fallout, McMahon was among dozens of state’s attorneys around Illinois to receive a letter from the judge overseeing the Van Dyke case asking them to consider taking on the prosecution.

When McMahon told people close to him he was considering the offer, many warned him against taking the assignment, said Daniel Purdom, McMahon’s former partner at the white-collar law firm Hinshaw & Culbertson.

“He took the case against the advice of people who thought it would be a difficult, no-win situation,” Purdom said. “He was told, ‘Don’t go near it.’ But Joe said it was the right thing to do. He didn’t shy away from it.”

McMahon said he signed on because he felt a “responsibility” to answer the call.

“The difficulty of the case, really that’s not a factor,” McMahon told the Tribune at his Kane County office. “Certainly, I knew that this is a significant case, … and at times it’s been more significant than I think any of us anticipated.”

A coalition of attorneys and activists that had fought for a special prosecutor exnewsed disappointment at McMahon’s appointment, saying he was an unknown quantity with no relationship with the Chicago communities most affected by McDonald’s killing.

McMahon said he knew when he signed up that he would be under a microscope.

“I just kind of accepted that before I started,” McMahon said.

Shaped by his days as a cop

Herbert, born in Chicago to a working-class family, is the youngest of three siblings, including a brother just a year older whom Herbert jokingly refers to as his Irish twin. Herbert’s mother, Barbara, was a nurse for more than three decades and is now retired. His father, Mike, was a Chicago police detective who retired from the department to became head of security for Devine, then-state’s attorney.

The West Rogers Park neighborhood where Herbert’s family grew up was a mix of police officers, firefighters and city workers. Herbert said the cops in particular seemed to him to be “the pillars of the community,” particularly his father, who died in 2006.

“He was as tough as nails, but he was also a gentleman,” he said.

Herbert recalled being awed by the way his father treated people with respect — even hardened criminals he’d arrested. On summer afternoons, Herbert and his friends often took the bus to the detective headquarters at Belmont and Western avenues so his dad could drive them to Comiskey Park for a White Sox game, he said. At the station, Herbert sometimes got to see his father interacting with prisoners.

“I was amazed at how fair and even gentle he was with some of these guys,” he said.

Herbert graduated from Loyola Academy in 1986 and went to Loras College, a small liberal arts college in Dubuque, Iowa, where he also played football.

“I was the slowest inside linebacker in the history of Loras College,” he joked.

After graduating in 1990, he had a brief stint at the Chicago Board of Trade before applying to the Chicago Police Academy in 1992.

Daniel Herbert, left, speaks before the judge as his client Chicago police Officer Jason Van Dyke, right, listens during a hearing at the Leighton Criminal Court Building on Aug. 20, 2018. (Antonio Perez/Chicago Tribune)

Herbert recalled his nine years on the force with fondness, particularly the satisfaction he felt taking “really bad guys off the street.” He worked in uniformed patrol only briefly before switching to plainclothes for various specialty assignments, including a stint at the old Cabrini-Green public housing complex on the Near North Side.

It’s clear that Herbert’s experiences as a police officer helped shape his perspective as a lawyer. One incident 23 years ago is particularly relevant to the Van Dyke case.

On the afternoon of Jan. 10, 1995, Herbert was with his partner investigating a burglary crew when a call came in about a home invasion in progress, he said. When they arrived on the scene, one of the suspects had just carjacked a citizen and sped toward them in the stolen car, he said. Herbert and his partner opened fire, shooting one of the tires out before chasing the car on foot onto California Avenue.

“I’m like running next to him with my gun in my hand, and I start punching the guy trying to get the keys out,” he recalled. “The car crashed at Devon Avenue, and the guy jumps out with a pistol. We opened up on him.”

The next day, a short story about the incident ran in the Tribune under the headline, “Suspect shot in wild chase.” The article said the man was in critical condition at a nearby hospital “with bullet wounds in the chest and leg” but did not name the suspect or the officers involved.

Herbert said he later testified at trial and the man was convicted of assault. He could not recall his name, however, and Herbert’s account of the shooting could not be confirmed by Chicago police or court records.

Herbert, who estimated that close to half of his firm’s business involves defending cops, said experiences like that put him in a unique position to understand the split-second decisions officers often must make on the street.

“As a policeman, you go on situations all the time that are potentially dangerous,” he said. “But before you fire your weapon, that’s a fear that you just feel it. It’s unique.”

Although he loved being a cop, Herbert wasn’t defined by it like his dad, and by the mid-1990s he started thinking about another career path.

While working, Herbert earned a master’s degree in criminal justice from Lewis University, and in 1997, he enrolled in law school at DePaul University, taking night classes. After earning his law license, he took a $20,000 pay cut in 2001 to join the state’s attorney’s office, starting out working narcotics cases at the 26th and California courthouse.

With his family connections to Devine, Herbert’s rise at the state’s attorney’s office was quicker than most. After two years, he was transferred to a felony courtroom in the busy branch courthouse in south suburban Markham — a coveted position for a young prosecutor.

“I think somebody did me a favor, to be quite honest,” Herbert said.

Devine said he personally had “nothing to do with” the move.

At Markham, Herbert got his first taste of prosecuting major violent crimes. As an assistant to two more experienced prosecutors in his first murder trial, he recalled being relegated to “carrying the cart” full of evidence to and from the courtroom every day.

Special prosecutor Joseph McMahon, left, and attorney Daniel Herbert, shown at an Aug. 3, 2018, hearing at the Leighton Criminal Court Building. (Antonio Perez/Chicago Tribune)

In 2004, after less than four years as a prosecutor, Herbert joined the FOP as the union’s in-house lawyer. It was largely a financial decision for Herbert, who then had two young kids. But it would wind up cementing him as one of the city’s most recognizable attorneys when it comes to defending cops.

In 2010, he set up his own private practice, contracting with the FOP to defend officers on everything from disciplinary hearings to criminal charges.

‘The responsible one’

One of five siblings, McMahon grew up in Carpentersville, a small town near Elgin. Much like Herbert, he describes his upbringing as typical. His father, Daniel, was a well-known real estate agent and active in local politics, while his mother, Anita, was a stay-at-home mother who later earned a nursing degree, working more than 25 years.

McMahon spoke warmly of his time at St. Edward Central Catholic High School in Elgin. At “St. Ed’s,” his father’s alma mater, he met his wife and developed a tight-knit network of friends.

The school is small and traditional — that is to say strict and rigorous, said McMahon’s longtime friend, John Sheehy.

“You could say it was a good school for discipline,” he said.

Even in a traditional setting, Sheehy said, McMahon stood out as the buddy who would keep the high school ski trips and bonfires from getting out of hand.

“The responsible one,” he said. “Every crowd needed one.”

Even years later, on a South Carolina golf vacation with old friends, he went on long jogs while the rest of the crew knocked back beers.

“We’d all come back, sit down, (have) a few more beers, and where’s Joe?
Well, he’s out getting his run in,” Sheehy said. “It’s that kind of discipline, you know? That’s kind of how Joe is.”

McMahon has run two Iron Man triathlons in recent years, but golf remains his favorite sport. Purdom, his former colleague at Hinshaw, said McMahon’s style on the golf course in many ways mirrors his demeanor in court.

“Golf is a steady-wins-the-race kind of game,” Purdom said. “Joe never changes his emotion, even when he hits a less-than-great shot. He just adapts and adjusts and thinks it through.”

McMahon studied finance at the University of Iowa and then put himself through John Marshall Law School in Chicago, working construction jobs and as a law clerk to support his young family. By the mid-1990s, he was rising up the ranks of the Kane County state’s attorney’s office, eventually taking over as chief of the criminal prosecution division, where he oversaw thousands of criminal cases ranging from misdemeanors to murder.

After stints in the Illinois attorney general’s office and with the high-profile Hinshaw firm, McMahon was appointed Kane County state’s attorney in 2010 when the previous top prosecutor was named a judge.

He has since been re-elected twice — though he has never been in a contested race in the staunchly Republican county, a fact that former state’s attorneys often rib him about.

Special prosecutor Joseph McMahon, left, speaks before the judge as attorney Daniel Herbert listens during a hearing in the shooting death of Laquan McDonald at the Leighton Criminal Court Building on June 28, 2018. (Antonio Perez/Chicago Tribune)

When his term expires in 2020, he will have been the longest-serving Kane County state’s attorney in decades. He expects to run for re-election but said he is hesitant to “look too far down the road.”

“I certainly have a lot on my plate now,” McMahon said. “I’ll make that decision when I need to. These things always kind of take care of themselves.”

Two trials, two convictions

Herbert’s profile as a cops’ attorney rose as the Police Department came under increasing fire over its treatment of citizens. In recent years, he has represented two Chicago police officers in high-profile cases that — like the charges against Van Dyke — focused on excessive force captured on video.

In both cases, Herbert argued vehemently that the videos did not tell the whole story and that the officers acted within the limits of their training. In the end, though, both officers were convicted by a jury and sentenced to prison.

While defending Officer Aldo Brown, Herbert argued in his closing remarks that surveillance video showing Brown beating a handcuffed suspect inside a South Side convenience store in 2012 “wasn’t even close” to proving excessive force beyond a reasonable doubt.

“You know how when you see a trailer of a movie and it shows a couple of funny clips and you think, ‘Wow, that’s a great movie, I want to go see that,’ ” Herbert told jurors. “And then, I think we’ve all experienced it, you go to the movie and you’re like, ‘Oh my gosh, those were the only two clips that were funny in the entire movie.’ Well, that’s what we have here.”

The stakes were even higher last year when Officer Marco Proano went on trial at the Dirksen U.S. Courthouse on civil rights charges stemming from an on-duty shooting in which Proano fired 16 shots into a car filled with teens, wounding two. Police dashboard camera video of the shooting showed that the car was backing away at the time Proano opened fire as he held his service weapon sideways in one hand.

A key part of Herbert’s defense was the implausible argument that Proano fired to protect the life of one of the teens hanging from the passenger window as the car reversed.

He also said the “split-second” evaluation made by Proano to stop the threat was justifiable under the law and that the video — without audio — did not capture the chaos of the moment.

“(Prosecutors) want you to look at this video and say, ‘Bad!’ ” Herbert said. “Well, that’s not enough.”

The jury deliberated just about four hours before convicting Proano of two felony counts of using excessive force in violation of the victims’ civil rights. He was sentenced last November to five years in federal prison.

McMahon’s record as Kane County state’s attorney does not feature any case as closely watched as Van Dyke’s — though to be fair, few would.

The office has in the past prosecuted suburban officers on charges of misconduct. Perhaps most prominently, ex-Elgin police Officer Michael Sullivan pleaded guilty in 2012 to planting evidence in a robbery investigation in an apparent bid to burnish his reputation so he’d be promoted out of the patrol division. More recently, another former Elgin officer pleaded guilty to felony identity theft after hacking into the email account of a fellow officer.

McMahon smiled when told that colleagues had described him as a “straight arrow.”

“It doesn’t surprise me,” he said. “I’m not someone with a flair for drama. I think people respect someone who delivers information to them straightforward, and that’s what I’m trying to do.”

The facts of the Van Dyke case are inherently dramatic without adding theatrics to the courtroom, McMahon said.

“I don’t think fireworks, I don’t think drama, is what ultimately convinces a jury,” he said. “I understand that I’m soft-spoken, but the jury will hear me and my team clearly on this case.”