Chicago’s Gangland Counterinsurgency

WIB front December 19, 2016 1

Aftermath of a Chicago shootout in 2016. Photo via Wikipedia Police are waging a campaign not unlike the U.S. Army’s in Baghdad in 2007 by...
Aftermath of a Chicago shootout in 2016. Photo via Wikipedia

Police are waging a campaign not unlike the U.S. Army’s in Baghdad in 2007


There were 470 homicides in Chicago in 2015, making it more deadly than all but 15 of the world’s 50 armed conflicts that year, according to data from the UPPSALA University Conflict Data Program.

“When you hear about … so many people in Chicago dying, it’s worse than some of the places we’re hearing about, like Afghanistan,” U.S. president-elect Donald Trump told Fox & Friends in September 2016.

While fact-checkers were quick to point out that, in 2015, the death rate in Afghanistan was far higher than that in Chicago, there are indeed numerous similarities between counterinsurgency wars and the Chicago Police Department’s battle against gang violence.

In order to disrupt insurgent or gang networks, counterinsurgents and police need to know how to find their adversaries — and how to disrupt their operations.

Most analysts and practitioners agree that the best sources of information are defectors from the criminal or insurgent network or from the surrounding civilian population.

This is especially true for the CPD, which often needs witnesses to publicly testify in order to convict gang members. It’s this key difference that makes domestic policing, to some extent, more difficult than counterinsurgency is.

U.S. Army major Sean Morrow, who commanded American troops in a predominantly Sunni area west of Baghdad’s airport in 2007 and 2008, described how he kept informants’ identities hidden from insurgents.

“We would run a free medical clinic,” Morrow told War Is Boring. “They’d come in, see the doctor, get what they needed for their families’ health, then on the way out… we would have an interpreter, an intelligence analyst and, whenever we could, a woman so that she could talk to the spouses.

“And we would say, ‘Hey, everyone knows you just came in here to see the doctor — this is your chance to help us understand what’s going on in the area.’ And we got a lot of information that way.”

But at the time, Iraqi law didn’t require public testimony against detained insurgents. Morrow said that, to his recollection, all the law demanded for a conviction was for a witness to provide a hand-written note and a drawing.

Brad Cummings, editor of the Austin Voice newspaper in Austin — one of the most violent neighborhoods in Chicago — took a similar approach to Morrow’s. Cummings used to coordinate confidential meetings between residents and police in order to help dismantle the drug trade in Austin.

The CPD hosts its own Community Alternative Policing Strategy meetings, which offer forums for residents to inform police about crime in their areas, but Cummings said that gang members and gang informants often attend these meetings, scaring off civilians.

Tim Brown, a CAPS community organizer in Austin, confirmed Cummings’ assertion. Brown added that sometimes even grandmothers of gang members act as gang informants.

Gang Leader for a Day: A Rogue Sociologist Takes to the Streets

To ensure the safety of the participants at his meetings, Cummings said he only invited residents he personally knew— mainly individuals who have called into the paper to complain about public drug deals. According to Cummings, the residents’ information helped the police to target drug areas they weren’t previously aware of.

The information wasn’t meant to help the cops target individuals, since — according to Cummings — this would have required residents to publicly testify and thus “put their life on the line.”

As Cummings and some CPD officers noted, there’s no way for the police to protect residents who rat out gang members, so even members of the community who trust the police are often unwilling to tip off the cops.

Steve Perkins, Director of Public Safety at Target Area Development Corporation, a grassroots organization that works to help marginalized communities in Chicago, explained that even though he knew which gangs accidentally shot out his window while his daughters were home, he wouldn’t provide the police information on the incident.

He emphasized that his decision had nothing to do with mistrust of the police. In fact, he said he often works directly with police in Englewood to improve the neighborhood. He “loves the police,” he said.

Instead, Perkins explained that his decision was motivated by cold reality — that there’s simply no way for the police to protect his family from gang retribution.

The CPD officers I spoke with, all on condition of anonymity, said they understood this point. One patrolman who has worked on the West Side of Chicago for many years recounted speaking with a woman at a public crime scene early in his career.

One of his supervisors pulled him from the conversation, saying that he was putting the woman’s life in jeopardy. Ever since then, the patrolman has been extremely cautious when soliciting information from the public.

This is a key problem in counterinsurgency, as well. COIN forces must protect their informants. But no army has enough resources to protect every resident all the time.

Minister George Bady, Jr., founder of Jehovah Jireh #1 Outreach Ministry, an organization in Austin that works to reduce violence and improve the community, expressed a similar sentiment.

And he pointed out another danger that comes with informing to police. “Nowadays, some of the police don’t care,” Bady told War Is Boring. “They want your information first and they say ‘Hey, we’re not going to tell them this, we not going to tell them that.”

Inept police often fail to protect even confidential informants, Bady said.

The U.S. Army’s Field Manual 3-24, which guided American counterinsurgency efforts in Iraq after 2007, cautions against “careless handling of human sources.” “Untrained personnel can result in murder or intimidation of these sources,” the manual warns.

One veteran police officer who spent most of his career in specialized units confirmed that unqualified officers often disclose the identity of confidential informants. “[The police will] put the name [of the informant] in the report,” the officer explained.

“It’s true,” the officer continued. “They put the name, the address, the date of birth — everything — in that report. And so it’s tethered to the defense initially … so the [defendant] reads it and he’s like, ‘Oh, now I know who whacked me, I got it.’ And they go back around and, boom, now there’s no case. They bribe [the informant], they do whatever.”

Why would police make such a brazen mistake? “A lot of it is just stupidity,” the officer said. “You know, they don’t care.” He went on to explain that the lack of mandatory training is a major contributing factor in such ineptitude.

The officer said that compromising an informant doesn’t just deter everyday residents from informing to the police. Criminals who would otherwise inform in exchange for a reduced sentence or parole might also hear of these incidents and refuse to cooperate.

It’s true that many criminals — and even some civilians — refuse to talk to police on principle. One patrolmen recounted an incident in which a gang member refused to tell the police who had shot him. “I’ll take care of it myself,” the gunshot victims said.

Still, losing the trust of these gang members is extremely detrimental to taking down the gangs, even more so than losing the trust of average citizens, the veteran officer said.

Information from citizens “is very rare,” he said — mainly owing to the risk of gang retribution, but also because “normal people don’t know the dirty stuff.” The veteran officer said that the vast majority of informants come from within the gangs themselves.

The officer expressed his frustration that, even when the CPD succeeds in recruiting gang informants, the gangs’ organizational structure can make it extremely difficult to take them down.

This is the second major similarity between counterinsurgency and the CPD’s efforts to curb gang violence in Chicago.

Chicago mounted police. Photo via Wikipedia


Chicago’s gangs, especially in African-American communities, are usually made up of a handful of teenagers and preteens with guns and a name. They’re anything but monolithic. As of 2010, Chicago’s 59 gangs included some 624 sub-factions.

Counterinsurgents and policy analysts understand all too well the sheer difficulty of dismantling such a decentralized criminal network. University of Chicago Assistant Professor Paul Staniland’s book Networks of Rebellion describes several types of insurgent structures.

Staniland explains that fragmented insurgent groups lack the sophistication necessary to carry out significant goals, such as fully controlling territory. For this, insurgents must elevate effective leaders.

One disadvantage of maintaining strong leadership, Staniland warns, is that the organization can be dismantled fairly quickly once counterinsurgents are able to penetrate top-heavy insurgent groups.

On the other hand, Staniland notes, “one advantage of a fragmented organization is that it can sometimes engage in low-level violence for a protracted period precisely because its lack of organization makes it hard for the state to fully wipe out.”

This is exactly what has happened in Chicago.

Back in the 1980s and ’90s, gang leaders could control their subordinates, which helped facilitate a more efficient drug trade. As Columbia University professor Sudhir Venkatesh notes in Gang Leader for a Day, a book on Chicago’s gangs in the late ’80s and ’90s, gang leaders banned small-time violence between gang members over personal feuds because it could disrupt the drug trade by drawing a police presence and driving away buyers.

Although the homicide rate in that era was higher than today’s rate, the gangs mostly targeted individuals who significantly disrupted the drug trade.

These hierarchical organizational structures ushered in an efficient and profitable drug economy. However, the same structure also made it easier for police to pin crimes of foot soldiers on their leaders once Chicago began applying the Racketeer Influenced and Corrupt Organizations Act, or RICO, in its counterdrug efforts.

Today, however, Chicago’s fragmented gangs oversee nothing like the same drug economy of decades past. On the other hand, they have been successful in carrying out sustained violence, despite tougher and tougher policing. The CPD “can’t infiltrate a bunch of kids that are on the block with a bunch of guns,” Cummings explained.

Networks of Rebellion: Explaining Insurgent Cohesion and Collapse (Cornell Studies in Security Affairs)

Community organizers and police alike noted that profiting off of drug sales is merely a secondary goal for today’s gangs. One officer explained that the philosophy of many gang members is, “Let’s go get enough money to buy a gun and then go shoot the gun at somebody … at our rival.”

Sources told War Is Boring that, for many Chicago gangs, killing rivals is the whole point. “The way to be known is to be the killer,” said Pha’tal, a resident of Englewood and founder of Think Outside the Block, an organization that offers young people alternatives to violence.

Some killings begin with personal feuds that play out on social media. Tio Hardiman — the founder of Violence Interrupters, which helps to deescalate personal feuds between gang members — estimated that 70 percent of Chicago’s murders resulted from these personal feuds. That remaining 30 percent of killings are drug-related.

The gangs’ fracturing has not only made it more difficult for the CPD to take down gang networks and changed the motivations for the violence — it seems to have also changed who gets targeted.

Bady, who spent 15 years in the 1980s and ’90s in the gang known as the Four Corner Hustlers, confirmed that gangs of that era used violence when necessary to protect drug sales. “It wasn’t a lot of senseless killing like shooting little kids, babies, things like that,” he said.

“If I was into it with you, I wouldn’t do nothing to your little brother, your sister, nothing like that.”

Cummings echoed this notion. “I could trust that the old gangs [of the ’80s and ’90s] wouldn’t shoot me indiscriminately, because they didn’t want to get caught. Now they don’t care about anything.”

Many of the police officers said they had the same impression of the indiscriminate nature of today’s gang violence. If the perceptions are accurate, Chicago gangs’ chaotic application of violence closely follows with how Stanford University professor Jeremy Weinstein predicted insurgents would act in his book Inside Rebellion.

Weinstein argues that when insurgent organizations lack strong leadership, subordinate fighters tend to employ violence opportunistically for personal enrichment and status.

U.S. Army soldiers celebrate Christmas in Baghdad in 2007. Army photo

Psychological operations

Morrow recalled how his unit in Iraq bought a basketball net online and “nailed it to a post and a piece of plywood like the movie Hoosiers.” The soldiers organized a basketball camp for local children.

Toward the end of the camp, Morrow’s unit decided to hand out free Qurans that his soldiers had bought at local shops. Morrow said he had no idea that most Iraqi families couldn’t afford personal Qurans. “It was a big deal.”

He recounted a phone call from a U.S. Army commander several miles away who had heard Iraqis in his area talking about “the American unit … that gave free Qurans out to the kids.”

“I always felt like that was the tipping point for us, in that intelligence increased,” Morrow said. “I felt like we kinda became part of the community after that.”

Such hearts-and-minds operations are common in counterinsurgency. They are, in fact, a facet of psychological operations. Efforts to influence the thinking of the local populace.

The CPD runs a bunch of hearts-and-minds programs. The department launched the Englewood/Police Youth Baseball League in 2015 “to strengthen relationships between Chicago Police Department and youth of the Englewood community through baseball,” according to the league’s website.

A good psychological op requires a media strategy. In the summer of 2016, the CPD helped National Public Radio produce a feature story about the youth baseball league. More recently, the CPD tweeted a video of several 10th District police officers wrapping presents for needy children.

The question is — why did this strategy work for Morrow, but has been less successful in Chicago? Part of the answer must be that bad police, in failing to protect civilians informers, have permanently burned bridges between the police and communities.

But another possible factor is the CPD’s long history of brutality, which has eroded public trust in the police to such an extent that restoring police-community relations will be a long, painful process.

On Oct. 20, 2014, CPD officer Jason Van Dyke shot and killed Laquan McDonald in Chicago. McDonald had a knife in his possession but was 10 feet away from Van Dyke at the moment the officer pulled the trigger. “It’s not new,” Pastor Ron Taylor, executive director of Chicago’s United Congress of Community and Religious Organizations, said of the McDonald’s killing.

Inside Rebellion: The Politics of Insurgent Violence (Cambridge Studies in Comparative Politics)

“We can go all the way back to Fred Hampton,” Taylor said, referring to the 1969 killing of the leader of the Illinois Black Panther Party by the Chicago police. The CPD alleged that its officers killed Hampton after being shot at, but many in the black community claimed that the police raid was a pretext to assassinating Hampton.

Although some of the police officers interviewed for this story said they have a problem with the current focus on police killings, many others said they understand that police misconduct has engendered mistrust, especially in African-American communities.

The same veteran officer who spent most of his career in specialized units acknowledged that, back in the 1990s when someone ran from the police, it was common for officers to beat up the assailant after catching them. “When I first got on [beatings after someone ran] was expected,” the officer said, adding that he’s glad the practice has largely ended.

For its part, the U.S. Army in Iraq was a foreign occupying force that many Iraqis perceived as brutal. Remember — U.S. forces sometimes dropped multiple 500-pound bombs on villages and towns whose residents commanders such as Morrow would eventually win over.

So why was Morrow more successful than the CPD is in improving community relations?

It seems that power and alliances are significant factors. In Iraq in 2007, many Sunni tribal leaders decided to pull their support from Al Qaeda’s insurgency against the American occupation — and instead aligned their militia forces with the United States.

The rapid decrease in attacks against U.S. forces — not only in Morrow’s area but throughout Iraq — is a testament to the extraordinary control Sunni leaders maintained over their subordinates.

By contrast, Chicago community organizers who work alongside the CPD to reduce violence do not have significant influence on the gangs. Bady, who often works directly with gangs and the police, summed up the frustrations of Tio Hardiman and many other community organizers in Chicago. “We can’t stop nobody from selling drugs because we ain’t have no jobs to give them.”

Sunni leaders in Iraq, on the other hand, received funding directly from the United States and, in turn, policed their own areas. There was an economic element in America’s counterinsurgency campaign in Iraq that’s missing in Chicago.

Now, insurgents can wage psychological operations, too — and not always to win the hearts and minds of the community. Often, insurgents conduct psychological operations in order to intimidate counterinsurgents, such as when a Syrian rebel organization produced a video of a rebel commander eating the heart of a dead Syrian soldier.

Media coverage of the Laquan McDonald shooting has had damaging effect on police morale. Cops are now generally more hesitant to proactively fight crime. They’re “worried that their interactions with uncooperative suspects will be video-recorded, posted online and misunderstood,” The Chicago Tribunnoted.

Some CPD officers expressed their fear that the current media narrative surrounding the CPD’s misconduct has caused politicians — and even the department’s top brass — to quickly punish potentially offending officers without proper justification.

Dean Angelo, Sr., president of the Fraternal Order of Police Chicago Lodge 7, said that officers feel they are working “in a different environment with people that are in political office who instead of running on an anti-crime platform, are running on an anti-police platform.”

Some officers said they believe anti-police sentiment — in particular, a 2015 lawsuit by the ACLU targeting the CPD’s investigatory stop policy — is emboldening gang members. “Hey, you know [gangs] run the streets, now,” one cop recalled a gang member telling him. “They do whatever they want. You guys can’t do nothing about it. And we all know it.”

Hardiman and other community organizers denied that gang members feel this way. But Bady claimed otherwise. “Think about it,” he said. “You used to be harassed by the police, they used to search you and tell you to move off the corner. So now since all these police shootings and lawsuits, they changed the law. So now you can’t touch the person. So now they can poke their chest out.”

Bady imitated a gang member as he continued. “‘What you doing over here for? Go about your business. Put your hands on me, I’m going to sue you.’ So now [the gang members] can leave the drugs over there and stand right here … what [the police] going to do? Even if you call the police and say, ‘This guy is sitting on the corner selling drugs,’ they can’t even go off that no more.

“They have to do surveillance and watch and see it. Unless you come out and say, ‘He the one selling drugs and the drugs right there’ — that’s the only way [to make an arrest]. But now you done put yourself in harm’s way.”

Patrick Burke is a freelance journalist who grew up in Chicago, but is now based out of D.C. You can reach him at, or follow him on Twitter @burke6112.

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