Daniel Herbert, left, faces the toughest case of his life in defending police Officer Jason Van Dyke.

By Wayne Drash, CNN

Chicago (CNN)With his tight buzz cut, angular face and square jaw, Daniel Herbert looks like a cop stuffed into a lawyer’s tailored suit.

There’s a reason for that. He traded in his uniform years ago and now is a high-powered attorney defending police.

Next to him this day in a Chicago courtroom stands Jason Van Dyke. The nation’s most notorious police officer. The cop who became a symbol of all that is wrong with police and their relationship with the black community.

Herbert knows what he’s up against by defending Van Dyke. He watched the now-infamous video of the shooting of 17-year-old Laquan McDonald long before its public release. His first reaction: “Boys, we have a problem.”

“That’s exactly what I said.”

Even at home, his 15-year-old daughter is “still pissed at me” for taking on the case. “She’s just livid,” he says.

A telephoned death threat against him was so real it forced him and his family to move out of their North Side home for a couple of days while police investigated.

“I wish I could shoot your f***king ass 16 times for something that is patently indefensible,” the caller said. “You shoot one of my people 16 mother f***king times, your ass going down.”

Herbert admits he has a soft spot for officers. It’s in his blood.

His father, Mike Herbert, was a highly decorated Chicago officer on the force for 36 years and served for several years afterward as the personal bodyguard of Dick Devine, then the Cook County state’s attorney.

The son followed in his father’s footsteps, becoming a Chicago police officer in 1992 and staying on for nearly a decade. Between patrols, Daniel Herbert attended law school. After he traded in his badge for the bar, he was a prosecutor before switching sides and becoming the go-to attorney for the city’s vast police force.

“I enjoy defending police officers. I think I’m good at it because I know the perspective of it,” he says. “The last thing a police officer wants to do is shoot somebody.

“This theory, or fallacy, that police officers want to get into deadly force situations couldn’t be further from the truth.”

He knows it because he’s been there. The memories from 20 years ago come back to him in a rush:

Herbert and his partner are chasing after a carjacking suspect in Chicago’s North Side. The suspect points a gun from his car and speeds toward the two cops in an alley.

Herbert fires from his service-issued SIG Sauer P226, blowing out two tires.

The suspect kicks his car in reverse, turns the corner and rumbles down Devon Avenue.

“I’m running alongside him all the way down the street,” Herbert says. “I’m leaning in his car because his window had been shot out. I’m trying to get the keys. I’m punching the guy trying to get the keys out.”

The car speeds up and smashes into a telephone pole. The suspect jumps out with a pistol drawn. Four officers, including Herbert, open fire. Blood spills everywhere.

“I went up and kicked the gun out of his hand and put handcuffs on him.”

The suspect survived and was convicted of an array of offenses, Herbert says, including aggravated battery of a police officer. Herbert was commended for his valor with a Distinguished Service Award.

Fast forward to 2014, another police shooting, in another part of town. This time with national implications.

Herbert may soon become a household name as the high-profile Van Dyke case progresses toward trial. He’s ready for battle.

“I will not back down from backing police officers.”

Even Jason Van Dyke.

The powder keg case

Much has happened since that night on October 20, 2014, when Van Dyke and McDonald crossed paths, ending with the teen’s body riddled with 16 bullets lying in the middle of South Pulaski Road.

In November, a judge ordered the release of dashcam video showing McDonald veering away from police as he held a knife, not lunging toward officers as police had said. Puffs of smoke showed McDonald’s body getting hit by bullets even after he was on the ground.

Chicago Mayor Rahm Emanuel has faced calls to resign over the case.

Protesters chanting “16 shots and a cover-up” called on Mayor Rahm Emanuel to resign. The police superintendent and the head of the independent police review board were sacked in the fallout. The Justice Department launched a federal investigation.

And Chicago voters, many of them angry over her handling of the case, recently denied Cook County State’s Attorney Anita Alvarez a third term.

At the center of it all is Van Dyke, the first Chicago officer charged with first-degree murder since 1980. Van Dyke has pleaded not guilty to six counts of first-degree murder in McDonald’s death.

If convicted, he faces a minimum of 45 years in prison.

Just two months before charges were brought, Herbert penned a piece for Chicago’s Fraternal Order of Police magazine about officers and the use of video against them. In retrospect it seems prescient, almost a portent of the case that would come his way.

“The prospect that an officer involved in the use of deadly force today may be charged with a crime,” he wrote, “is very real and extremely troubling.”

Driving around Chicago now, Herbert calls the first-degree murder charge against Van Dyke prosecutorial overreach. Involuntary manslaughter or second-degree murder, maybe, Herbert says, but not first-degree.

“First-degree murder is not for somebody who reacts to a situation and may or may not be correct,” he says. “My client didn’t wake up that morning with the desire to kill somebody — let alone Laquan McDonald. He simply reacted based on a split-second decision.”

Of course, not everyone agrees, and court observers say they don’t envy Herbert’s task.

“He’s got a very tough case,” says Chicago attorney Jeff Neslund, who represented McDonald’s estate and negotiated a $5 million settlement with the city in April 2015.

Neslund and Herbert have known each other for decades. Neslund and Herbert’s older brother, Mike Jr., were classmates at Loyola Academy, the prestigious Jesuit prep school in the northern Chicago suburb of Wilmette. When Neslund was a prosecutor, he called Herbert, then an officer, to the stand as a witness several times and found him credible.

The thing that makes Herbert stand out as a defense attorney, Neslund says, is his background. “He’s got a unique perspective to do the work he does because No. 1, he was a policeman and No. 2, he received training as a prosecutor,” Neslund says.

“He’s basically got the playbook as a former state’s attorney.”

If Neslund were defending Van Dyke, he said, the best legal advice he would give would be to “plead insanity or say your trigger just got stuck.”

Even with that, Neslund says, good luck.

“What’s going to be most problematic for the defense is to try to explain or justify continually shooting this young man while he’s on the ground,” he says.

University of Chicago law professor Craig Futterman played an instrumental role in the video’s release, working with a journalist to push back after a Freedom of Information Act request was denied. Futterman has remained a bulldog on police issues, seeking the release of police misconduct reports and other documents — much to the ire of the department.

Still, he understands Herbert’s role in defending Van Dyke: “It’s critically important that good counsel are willing to represent even the most hated defendants.”

Daniel Herbert, left, faces the toughest case of his life in defending police Officer Jason Van Dyke.

Only natural to become a cop

The youngest of three children, Herbert was surrounded by police as a boy. His father and many of the men in Rogers Park, on the far north side of the city, were on the force.

“A lot of police grew up in my neighborhood,” he says. “Good role models.”

His father was more than just an officer. He was the neighborhood’s beloved youth football and baseball coach. His love for baseball continued long after his two sons and daughter were grown. Mike Herbert had a second career as a scout for the New York Mets and the Detroit Tigers.

But his passion was for the Chicago White Sox. Despite battling lung cancer, the elder Herbert toted around an oxygen tank to every Sox playoff game in 2005, hanging in long enough to see his favorite team win the World Series. He died a few months later at the age of 67.

The son carries on that same love for the White Sox, sporting “WHT Sox 2” on his license plate on the back of his Lexus sedan.

But it’s those early lessons from growing up around police and seeing them as honorable that resonate most with Daniel Quinnan Herbert.

He was even named after a slain Chicago police officer. Daniel Quinnan was his father’s first partner and was shot and killed by a suspect during an armed robbery in the West Loop in 1966, two years before young Daniel was born.

And so it seemed only natural to become a cop. For nearly 10 years, that’s exactly what he did, beginning in the Uptown neighborhood in 1992 and patrolling other neighborhoods in the city’s north.

But he had higher ambitions. While an officer, he attended night school and earned a master’s degree in criminal justice from Lewis University. He eventually earned a law degree from DePaul University.

In 2001, he left the police beat for the Cook County prosecutor’s office. As an assistant state’s attorney, he prosecuted DUIs before graduating to the felony narcotics unit, going after more serious crimes such as armed robbery, sexual assault and murder.

He was the lead prosecutor on more than 100 trials in his four years there. He says his supervisor at the time, Anna Demacopoulos, believed he was “a little too pro-police” and once put him on a case against a cop selling prescription pills “to kind of show me a lesson.”

“I told her I loved it,” Herbert says. “The guy was a scumbag.”

Demacopoulos is now a Cook County Circuit Court judge and said her role prevented her from being able to comment for this story.

In 2005, Herbert left the prosecutor’s office to become the lead attorney for the Fraternal Order of Police, representing members of the city’s 12,000-strong police union on everything from real estate closings and personal injury cases to disciplinary hearings and other accusations.

“He’d be the first guy they call,” Neslund says.

Herbert represented the union for five years before opening his practice in 2010. In 2014, he was named one of the “Top 100 National Trial Lawyers” by the National Trial Lawyers Association.

His office is filled with staff who, if they aren’t former police officers, are children of cops or married to one. He remains the guy police turn to when they need counsel.

“Anytime you see an officer in the news who’s in trouble,” Neslund says, “for the last few years it has always been Dan Herbert representing them.”

When Herbert talks about the Van Dyke case, his words can sometimes have the familiar ring of some of the most ardent protesters. He accuses Chicago’s mayor of a cover-up for his own political survival, an allegation Emanuel has denied.

“The mayor kept this thing from the public because he was in a tough runoff,” Herbert says, “so his office did everything in their power to keep this tape from being released.

“This tape being hidden, for lack of a better word, it created such a political storm.”

Yet Herbert also makes comments that could offend many of those same people.

Police on the scene, he says, did not participate in covering up the shooting, even though at least five officers said McDonald charged at Van Dyke with a knife in a threatening manner, contrary to what the video shows. At least three witnesses have alleged police questioned them for hours, threatened them and ordered them to change their accounts to match the official police version.

Herbert blows off those allegations: “It makes for a good story, but in reality I just don’t think there’s any evidence of it.”

He’s come around since his initial reaction to watching the video.

“That was before I had spoken to my client and some of the other police officers on the scene. And it was before I had watched it probably 100 times.”

Van Dyke approaches the bench during a March procedural hearing.

It is the home of Circuit Judge Vincent Gaughan, who has seen his fair share of high-profile cases over the years, from singer R. Kelly’s acquittal in a child pornography case to the trial of the man convicted of killing Jennifer Hudson’s relatives.

On a recent March day, Gaughan presided over procedural matters in the Van Dyke case. Twenty-seven petitioners, including the Rev. Jesse Jackson, had asked the court to assign a special prosecutor, saying the state’s attorney’s office has a conflict of interest in trying the case. Van Dyke, who remains free on bond, also asked the judge to wave further pretrial appearances, citing safety concerns.

Those matters will be decided at a later date.

Court observers say the issue of a special prosecutor adds another layer of intrigue to the case — a tactic that could backfire drastically for those wanting Van Dyke locked up. If a special prosecutor is assigned, they say, expect motions by Van Dyke to dismiss the case entirely for failure to get a speedy trial.

The issue raises other questions: Would the current state’s attorney share all the evidentiary material with a special prosecutor, or would the special prosecutor need to start from scratch?

For this hearing, Van Dyke is dressed in a royal blue shirt, red tie and a dark-colored suit. His sandy brown hair is combed left to right.

He arrived at the courthouse early, slipping in before it was open to the public. There was no phalanx of protesters outside court as there have been for previous hearings.

His father sits next to Van Dyke on the front row of the court’s oak benches. Van Dyke looks like a spitting image of his father, except for his dad’s white hair and the dark circles beneath his eyes.

The father’s face seems to be frozen in perpetual sadness, the gravity of his son’s case weighing him down.

Looking at Van Dyke, one can’t help but wonder what’s going through his mind. How often does he think about the encounter? Why did he fire 16 shots? Does he replay the shooting in his mind on an endless loop like the video that’s been seen by millions?

“He definitely regrets that he became involved in this incident,” Herbert tells me. “It’s completely changed his life. He is upset that he was put in a situation where he had to take someone’s life — anyone’s life — let alone the individual here.”

Herbert would not make Van Dyke available for this story, saying he speaks for his client. A gag order prevents Herbert from speaking about his legal strategy.

Even asked about the 16 shots, Herbert holds his cards close to his vest.

“Honestly, it’s so hard to judge somebody’s actions unless you know everything that they were thinking and experiencing at the time they used deadly force,” Herbert says. “And nobody knows that, other than me and a couple of people who are part of my trial team.”

Few details have been revealed about Van Dyke’s life beyond the shooting and a history of misconduct complaints against him for excessive force, use of racial slurs and other allegations. None were substantiated. However, a civil jury awarded $350,000 to a man who said Van Dyke used excessive force against him.

Herbert provides some tidbits about the officer’s past: He was born and raised Catholic in the Chicago suburb of Darien and played football, basketball and baseball in grade school. At Hinsdale South High School, Van Dyke played football for a couple of years and participated in the band.

He went on to study criminal justice at the College of DuPage before attending the University of Illinois-Chicago. The Chicago Police Department hired him in June 2001. He eventually earned a degree in criminal justice at Saint Xavier University while an officer.

In his nearly 15 years on the force, Van Dyke patrolled some of Chicago’s most dangerous areas, including the notorious West Englewood. He earned more than 50 awards during that span, including recognition for reducing crime and serving at the 2012 NATO summit.

He had never fired his weapon in the line of duty before the night of October 20, 2014, Herbert says.

“He probably sees more violence and disturbing situations in one night than the majority of the public sees in their entire lifetimes,” Herbert says. “Despite him working in this war zone for 15 years, he’d never shot at anyone before that night.”

Van Dyke, he tells me, volunteered for security around then-Sen. Barack Obama’s Chicago-area home when he first ran for president. Van Dyke also served in the security detail on the parade route in Washington for Obama’s second inauguration in 2013.

“I just think it speaks to him wanting to do the right thing without promoting himself,” Herbert says. “He liked the idea of a Chicago president and may have liked the idea of the first African-American president.”

Van Dyke, who was suspended without pay from the force, has managed to work manual labor jobs to stay afloat since he was first charged late last year. He has applied to get a trucking license, possibly to haul freight, Herbert says.

He was recently hired as a janitor by the police union.

While awaiting trial, Van Dyke lives at the same home with his wife of 14 years and two elementary school girls. “He’s a real closed guy,” Herbert says. “He’s a man of few words.”

He adds that Van Dyke doesn’t “want to talk to anybody about this” but knows he’ll have to when the case reaches trial.

As for the cop-turned-attorney, Herbert newses on, putting on a face of normalcy for a case that is anything but.