Jim Sherlock, a retired Chicago homicide detective with four generations of CPD ties, reveals how his 1989 gang unit resolved crimes through direct negotiations—until media scrutiny forced a shift to rigid enforcement. On the South Side, he saw residents cooperate despite claims of distrust, yet cold cases piled up due to lost institutional knowledge. Now, with Chicago’s crime surging 38% since Mayor Brandon Johnson’s 2023 takeover, Sherlock blames weak prosecution, no-cash-bail policies, and mayoral rhetoric fueling gang impunity. He insists racial dynamics are oversimplified, targeting systemic failures like quick suspect releases and police avoidance of confrontations. Aggressive enforcement, he argues, is the only solution—but corruption persists due to unchecked unit autonomy, proving real crime-fighting demands more than TV’s dramatic myths. [Automatically generated summary]
Welcome to this week's interview with retired Chicago police detective Jim Sherlock.
As you know, Chicago is out of control.
The crime in Chicago has risen 38% since Mayor Brandon Johnson assumed office on May 15th.
Gangs are now being asked, please don't shoot each other between the hours of nine and nine so that children are less likely to be killed.
That sounds like it's going to really do well.
Even the mayor, although he doesn't say it by name, admits that some of this is due to Kim Fox, who was the nation's first big city prosecutor backed by bond villain George Soros.
I wanted to talk to Jim Sherlock because he is not just a retired Chicago homicide detective and cold case detective.
He comes from a family of service with four generations, nearly 100 years with the Chicago Police Department.
So he's basically blue bloods come to life.
Jim, thank you so much for coming on.
I appreciate it.
Thank you, Andrew.
Thank you for having me.
Well, to begin with, could you just explain to the audience what your career was like?
How you got into the police department and what you did there?
Sure, sure.
Well, as you said in the intro, I come from a police family.
My great-grandfather, my grandfather were Chicago police officers, and my dad's brother was a Chicago police officer.
So I always wanted to go into law enforcement, but I had an incident that happened to me when I was 14 years old.
I was robbed.
I grew up on the south side of Chicago in the Marquette Park area.
That's pretty famous for a lot of the Martin Luther King marches, civil rights marches.
Great place to grow up, but it was a tough area.
So I'm 14 years old and I'm walking down the street only a few blocks from my house and a car pulled up and some guys jumped out and they surrounded me and they put a knife to my chest and they demanded everything I had.
And now when I look back on that, what the heck does a 14-year-old kid have?
So I didn't have anything.
So they stabbed me anyway.
They took off, got away.
I didn't get much of a description, but I went home and I was, for some reason, I was a little nervous about telling my dad what happened.
But I told him what happened.
I showed him the injury I had in my chest.
It was still bleeding pretty bad.
I didn't go to the hospital.
I mean, I guess we didn't worry about infections in my family.
But so my dad made a phone call without my knowledge.
And within an hour, I had six of the scariest men I've ever seen for being a 14-year-old kid.
These guys are all, they look like bikers, you know, and they were sitting in my dad's garage and they wanted to know what happened.
And it took about 15, 20 minutes for me to figure out that they were the police.
And so I give them all the information I had.
And then within a day, they came back to my dad's house and they said, hey, everything's taken care of.
Those guys won't be roaming the neighborhood anymore.
I never found out exactly what happened.
But after that event, I really wanted to be the police.
And then when I joined the police academy in 1989, one of those officers that was in my dad's garage, I became very good friends with.
I learned that they were all gang crime investigators.
So they were semi-undercover, but they knew everything that was going on.
And they were a bunch of good guys.
A couple of them were Vietnam vets.
So I worked with those guys for a very short while until they retired.
But that was really the driving force that made me join the police department.
You're talking about a depiction of police that is nowadays, I think, considered old-fashioned.
I mean, it sounds like these guys didn't go to trial, and this was handled kind of off the record, which is actually sometimes the best way for things to be handled, even though you can't get away with it as easily today.
When you joined the police department, was that still going on?
Because, you know, if you ever watch that show, Blue Bloods, they sort of talk about, well, in the old days, we did it this way, but now we do it much more by the book.
Is that so?
Or I should ask, is it so in Chicago?
Well, when I came on, like I said, in 1989, it still was going on.
They still had the gang investigators and they had a gang crime unit.
And these guys and women, they were called upon when there were problems, serious problems, like robbery sprees, gang fights, and anything that was going on downtown Chicago.
If the mayor wanted it taken care of, he would call that unit.
And then they would develop all the intelligence or they would use the intelligence that they gathered.
And they would be able to get to the leaders of these groups, of the gangs.
And they would basically, I learned later, they would basically have a meeting with the gang leader and say, hey, this is going to end now.
We're not going downtown to the Rush Street area.
We're not doing this.
We're not doing that.
And they had an understanding.
So that was there.
But that was 89 to about probably about 1988.
I'm sorry, 1998, 1999.
It was changing.
And then they got rid of that unit and we became a softer, more of a belly rub unit with the problems on the street.
Did that come from pressure within the department or pressure outside?
Actually, what I should ask is, did that come from pressure within the city or did it come from pressure from the media and outside the city?
I believe it came from the media.
The media was pounding us hard for a few years.
And also, it just came from attrition.
A lot of those guys, those Vietnam vets that I worked with, they just retired.
So when I was in the academy, all my instructors were from that era, and then they retired.
So I think the whole environment came.
But I think to your question, I think the media had a big role in it because they would avoid a lot of major incidents that happened, and then they would focus on what the police did to handle it.
So it just, everything shifted to the police are doing this wrong, the police are doing that wrong, the police are too brutal.
When, in my opinion, the crime was getting more violent.
I mean, the violence in Chicago is still on the rise, as you said in your intro, and it's way out of hand.
And we don't have that niche anymore to be able to call on a unit like that to go handle the situation.
Yeah, and I mean, Dealey, I often think that when I'm watching the news, the guy talking really doesn't have an understanding of just how savage gang life can be and how lawless streets can become when the gangs are in charge of them.
It's almost like a fantasy that you're going to go in and wag your finger at people and they're going to get better.
But you moved on from there to homicide, right?
Yes, I was promoted to homicide detective in 1996, and I was working the South Side.
So that was jumping right into the fire with that.
It was a great job.
I was surrounded by a bunch of very good detectives.
So I learned a lot real quick.
It was a lot of good work was going on there.
But just as I said earlier about guys retiring, that group, that generation of detectives that were so good at what they did, they all started retiring right when I made detective.
And that's when the department, in my opinion, started changing.
You know they, these old, they used to call them Patties or Murphys.
Those guys were all on the way out and they were being replaced by what the media.
They were saying it's a more diverse police department.
You know uh, and that's.
That was a change that took place quickly, quickly.
So when, when you walk into a neighborhood and there's a murder uh, you know on, when you watch this on tv, it seems like it's very hard to get people to talk to you.
Does it help to have a diverse force to get people to talk to you if they're a different race?
I mean, is there any benefit to that?
Or is it still an impenetrable culture that you're dealing with?
You know, I think that's the media that make this like people aren't talking to us.
I don't want to say me, our team, we didn't have a problem with that.
If the murder happened to happen in a black neighborhood, people were coming out to help us.
I never experienced where like everybody was clamming up and they wouldn't talk to us.
People wanted to do the right thing and help us.
Now, not enough people, unfortunately, but people were helping us.
And I would read in the paper that people don't trust the police.
They don't want to talk to them.
They're scared of the police.
I didn't experience that.
When my partner and I would pull up on a homicide, the patrol officers were there protecting the crime scene.
We come up.
We always had somebody tapping us on the shoulder.
Now, they wouldn't give up exactly who the shooter was or who the offender was in that, but they would point us in a direction that would help.
So it wasn't as bad as the media would say that the neighborhood hates the police.
They don't trust the police.
There were a lot of, I worked in Inglewood, which at the time was the worst neighborhood in the country.
We always had good people from that area would find us when no one was looking and they would try to point us in the right direction, not giving us the name of the offender, but giving us, helping us.
So I never bought that whole thing about all the people in these south side and the west side neighborhoods don't like the police.
There were a lot of good people in those areas that were helping us.
Yeah, no, that makes perfect sense to me.
Nobody wants to be the victim of crime.
Why should they?
Right, exactly.
You know, we're talking to Jim Sherlock, retired Chicago detective.
Before we get onto what's happening in Chicago today, I have to ask you, just out of pure curiosity, you went on from homicide to do cold cases.
How do you find the cold cases that can be solved, or can they ever be solved?
That's a great question.
And you know what?
Most of them know they can't be solved.
You know, Andrew, I would read a lot of old reports, and in the reports, they would say, yeah, they found a bloody napkin on the scene, and they would just note it in the report, and they wouldn't recover it.
They didn't know any better back then.
So there's a lot of evidence that was overlooked.
So you pick up a case with a cold case, and there's very little evidence in that case.
So without the evidence, it'll take an admission or it'll take an eyewitness to come forward.
So those cases are really hard to solve.
But once like the 80s and the 90s came around, police officers knew enough to inventory everything.
If there was that bloody napkin on a scene, they would inventory it and we'd be able to put that in the code as for the DNA.
But the cold cases in the unit I was on, we were trying to solve cases from the 50s, the 60s, and the 70s.
Those were very difficult.
Obviously, people are dead.
And we had success.
I had success in a couple of them that just got lucky where people were still alive.
And they basically told me, no one's ever talked to me, but this is what happened.
So you get lucky.
So you're looking at the city now and it's really suffering.
And all the talk about how evil the police are, and we'll get to that in a minute.
But before we get to that, most of the people who are being harmed and killed are being harmed and killed, not by police officers, obviously, but by very bad guys.
You have to look at this and say to yourself, and the new mayor who's been brought in was not the guy I would have sent in to solve the problem.
And the way he's speaking doesn't encourage me that he can solve the problem, even though he did point out that prosecutors who won't prosecute crime are a problem.
But he's still got that kind of soft soap rhetoric that I just think is just encouraging to criminals.
You've got to be sitting there and thinking, if I were mayor or if I were in charge, I would do this, this, and this.
What would you do?
What were the kinds of actions you would take that could be taken to bring down crime in the city out of control?
Well, what I would do, first of all, is I would enforce the laws that we have on the books.
And right now, the big thing in Chicago is a lot of people are taking over intersections.
Like they block the intersection off, and the cars are flying around.
And if you happen to be an unlucky citizen walking by, they're knocking you to the ground.
They're taking your purse away.
And the police are actually standing back.
They're letting this happen.
And they're just trying to prevent people from getting hurt from driving into the situation.
But as you said earlier, when you have a mayor that condones this kind of behavior, and he was worried a little while ago, he was worried about some of the media were referring to them as a mob.
Well, that's what they were.
It seems like we're more, this mayor is more concerned about what people are calling the people than actually trying to do something about the crime.
And I'll go back to when I was in a gang crime unit.
If that happened on the street, we would be looking for the leaders of this because you can always tell who's leading this.
We would look for the leaders and we'd have a great supervisor that would say, that guy over there, grab him.
We need him.
Then we would grab him or however many guys and we would arrest them.
And then the state's attorney's office, unheard of, right?
They would actually cooperate with us.
And they would say, we would tell them what happened.
We'd do our reports and they would prosecute.
They would try to put these people in jail.
So now nobody's held accountable for what they're doing.
So they don't care.
They just don't care.
I just did a private security job, Andrew, downtown Chicago for the last three days.
I spent 14 hours in an SUV with tinted windows watching some VIP people as they were going from restaurant to hotels.
What the four or five guys, what we all saw, were all retired detectives.
What we saw is incredible downtown.
There are these people that are going from restaurant to restaurant to hotel, just walking around, having a good time.
They have no idea they're being preyed upon.
We're watching all these cars drive around and they're looking for people to rob.
And, you know, we ended up having to tell a few of the police cars that were driving by, hey, you know, there's a Ram Charger driving by.
They just keep circling and three of the four guys got masks on.
You know, why don't you pull them over?
And some police out of incompetence won't do it because they just don't want to do it.
And the police, the aggressive police who want to do it, they're second guessing themselves because they know if there's any kind of confrontation, they're going to get no backing.
So it's really a catch-22 situation where the police that want to do the right thing are hesitant.
Because as soon as you pull a car over, there's going to be some type of incident that occurs.
And that's the last thing the police want.
Cops and Guns00:08:14
Because when the media gets a hold of that video from the officer's body camera, it's going to go on that night's newsreel, and they're going to show only what they want to show with the police officer saying something or grabbing the individual.
So cops don't want to get involved in that anymore.
And that's bad for the citizens.
You know, so much of this has to do with race.
There's no way of not talking about this.
It's amazing to me that the police are the ones who are blamed for the fact that there is simply a lot of crime in black neighborhoods.
I mean, obviously, you know, the politicians who make the policies who let that crime fester and the cultural people who tell you you don't need whole families to raise kids and things like that, they have no responsibility.
It's just the cop who's the last guy who has to deal with the problem who is blamed for racism.
So let me ask you a straightforward question.
You're living in a city where a lot of the crime is being committed by people with a certain color skin.
After a while, do you feel that that causes you to be racist to say to yourself, these are bad people?
Or is there some other way that you have to deal with that mentally to simply move through that as a fair, honest police officer?
Well, in my case, I never had that problem because I never bought into this thing that it was a black-white problem.
I didn't.
I thought that was what the media and these activists, they want this impression that everything is white and black.
It's the white people against black people.
They want that to draw the attention away from what they're actually doing.
I work with several partners that happen to be black, and they were just upset with what was going on in the city.
And also, like I said earlier, there's a lot of black people that would come and help us with, and they're tired of it.
They're tired of the nonsense, but they don't show that on the news.
So it comes across as a white-black issue when at the end of the day, it's just a small portion of these thugs throughout the city who, like you said, right now they're black and they're preying on people and they're preying on people because nothing's happening to them.
And they know that nothing's going to happen.
Even if they get arrested now with this no cash bail, they're walking right out of jail.
But the people that I know that I deal with, the black people, they're most upset about this because also, like you said, most of the time they're the victims.
But then when you turn the news on and you listen to this mayor and the last mayor, it's, you know, the police are doing this because they pulled the car over because they were black.
Well, a lot of these officers work in districts that are 99% black.
And now every time they pull the car over, the response is, you pulled me over because I'm black.
And the officer's like, there's nobody else around.
You know, you went through a red light.
Everybody's black around here.
So it's this whole race thing always irritated me and the guys that we work with.
We're like, if I worked in an all-white area, I'd be pulling over white people.
But right now in the city of Chicago, the South Side and the West Side, it's a fact.
That's where all the crime, all the major crime is happening.
And right now, the offenders of the worst crime we're having right now, obviously the worst is murder, but there's carjackings, Andrew, all over the city.
And those by and far are done by young black males.
And the reason why so many are happening is when they get caught, the Cook County State's Attorney's Office finds a way.
If there's four guys in the car, three of them are released right away.
They're not being held responsible.
And then that driver will spend a night in jail and then he's released.
So what are those guys going to do?
They're going to go home, watch some video games, and that night they're going to go right out and do the same thing because there's no consequences.
It's a cycle.
It's a cycle right now that's got to be stopped.
If it's not, it's going to keep getting worse.
It's amazing.
What about guns?
I mean, this is another thing we hear about all the time: the gun laws in Chicago and Illinois are very tough, and yet gun crime is rampant.
People are being picked off every weekend, it seems like in double digits.
What would you do about guns?
Is that the problem?
Is that a problem?
I mean, obviously, guns in the hands of bad guys is a problem.
How would you deal with that?
First of all, I'd like to say this: I'm so tired of hearing politicians and news people of calling it gun violence.
There's somebody pulling a darn trigger.
I mean, I turned the news on and they want to say gun violence.
They just can't wait to say gun violence.
You got someone pulling a damn trigger.
You know, when somebody uses a car to kill somebody in a DUI, they don't blame the car.
They're blaming the guy driving the car.
You know, it's, you know, but the way to do it is when I talked earlier about the gang unit, so they had a citywide gang unit, and their job was street enforcement, it was getting guns off the street.
It made it to the point where these gangbangers, these thugs that were preying on people, they didn't want to carry a gun in a car because the chances of them getting pulled over was very high.
If a gang unit drove by a car and there were four guys in the car and they gave them the old eye, the old eyes, you know, trying not to look like they're out robbing people, they're getting pulled over.
And if there was a gun in that car, all four people were getting charged with that gun.
That's the way it was back then.
All right.
That's what they need to do now.
They need to make it.
So it's against the, it is against the law, but they need to go to jail and have to know that they're going to jail if they get pulled over with a gun in the car.
Because I'm going to tell you right now, both my sons are on a job now.
They're both police officers.
And very few officers are stopping cars.
Very few.
So this enforces the gangbangers and the people doing the carjackings.
They're all carrying guns in the cars because they're not worried about being pulled over.
As 15, 20 years ago, you get pulled over, you're going to jail.
You're going to jail.
So we have to, as you said earlier, we already have the strictest gun laws around, just enforce the damn things, but we won't.
Yeah.
Is there a problem?
I mean, it always seems to me that they put together special units who are sent out to get guns off the street, to get drugs off the street.
And there's always, there's not always, but there's frequently a problem with corruption.
They become kind of prince of the city types at Rampart in LA.
There was a gun task force in Baltimore that they made a film, wrote a book about, made a film about.
I know Chicago had a gun task force with problems.
Is there some way to deal with police corruption where you don't cripple the police?
Yeah, that's a great question because police corruption, in my opinion, is always going to be there.
They're human beings.
You know, when they form these units, Andrew, the supervisors, historically, we've had great supervisors in these specialized units.
So they do the best they can to get the best people that are coming from districts.
Like they'll go to a district, like a very busy district, and they'll recruit officers out of that district to work in these special units.
But I've seen it happen so many times where they have so much freedom in these units.
They're not going to domestics.
They're not handling traffic accidents.
Their main job is to seize guns off the street.
The problem with that is all that freedom, and then some of these guys go rogue.
I don't know if there's a way to root it out completely, but the better the supervisor, the less chance that you're going to have that.
If you have supervisors that are watching these guys and making them accountable for what they're doing, you know, keep, I don't want to say they're babysitting them because once you start babysitting police officers, that makes it worse.
Coppers can't, you know, they hate that.
Coppers Hate Change00:02:20
What do coppers hate the most?
They hate change and hate when things stay the same.
So they're a hard group to appease.
So the right supervisor can stop that, I believe.
Completely, no.
So the last question I got to ask you this, I used to work in Hollywood, and it always used to make me laugh, I guess, laugh kind of bitterly, but still that some handsome guy who's never done anything for anybody can make $250,000 a week, a quarter of a million dollars a week, pretending to be you, who I suspect made considerably less than that.
Are there any TV shows or movies or even novels that you read where you go, yeah, that's what the, that's real.
That's what the police are like?
You know what?
The show that reminds me most is Barney Miller.
That was the show that I thought portrayed exactly what being a detective was all about.
Because when I was working in the area of homicide, we were all in the, you spent a lot of time in the office playing jokes on people.
That was the most I would say that reminded me of what police work was really like.
As far as NCI seeing it, these popular shows that are on, I don't, I mean, first of all, yeah, they're all good looking and everyone's always so tense walking around like this is happening, that's happening.
But it's not like that.
The guys and gals that work in these detective divisions, they work their butts off, but they're not walking around all tense and what are we going to do now?
A lot of it is playing practical jokes on each other, going to eat with each other.
But then you have the serious, unfortunately, and then you have, you know, you'll be sitting there and then your supervisor walks up and says, hey, we got a fresh one.
And then you got to, now you got to tone everything down and go out and you got to act professional.
But I always thought Barney Miller was my show that showed exactly what being a detective was like.
That's really fun.
I'm going to go back and watch it again now.
Jim Sherlock, thank you so much.
Former retired homicide detective from the Chicago PD.
I hope you come back and talk again.
I really enjoyed talking to you.
I will, Andrew.
And thank you for having me.
Have a great day.
Thanks.
You too.
All right.
Come to the show on Friday for the Andrew Clavin Show.
That was this week's interview with Jim Sherlock, retired police detective.