Originally published on Dec. 20, 2015

After pleading guilty to robbing Mayor Rahm Emanuel’s teenage son and apologizing in court, Phillip B. Payne got a break.

Cook County Judge Lori Wolfson sentenced Payne to three years of probation, telling him she thought he “is not a violent person” and is “capable of doing well.” She also ordered him to stay away from gangs and drugs.

But since his sentencing earlier this year, the wiry 18-year-old known as “Peejay” hasn’t managed to do that, according to interviews, court records and his own social-media posts.

An admitted gang member, he’s now being held in Cook County Jail after a turbulent spring and summer in which he was arrested twice, accused of dealing cocaine and driving a stolen car.

In between, he grieved the loss of his older half-brother — a fellow gang member who was shot and killed in April, a casualty of what appears to be a North Side gang war.

The crime that put Payne in the public eye — rolling Zach Emanuel for his iPhone on a sidewalk outside the mayor’s Ravenswood home last December — remains under investigation. That’s because the police say they still don’t know who was Payne’s accomplice in the nighttime attack on the mayor’s 24/7 police-patrolled block.

What’s happened to Payne in the year since the mugging, though, is emblematic of a larger problem confronting Chicago. Like many young people from broken families, he has immersed himself in a gang culture that breeds everything from robberies like the one that touched the city’s first family to the gun violence that has wracked some city neighborhoods.

That point isn’t lost on Payne’s grandmother, Loretta Jackson. She recently buried one grandson, Payne’s brother, BoShaun D. Jackson. And she is praying that her jailed grandson, still a teen, can turn his life around.

“Right now, he’s at a crossroad,” Jackson, 78, said of Payne. “I wrote him in jail, and I told him, ‘Do you want to go down the same road as your brother?’ . . . He don’t know nothing else, so he’s doing what his brother trained him to do.”

Part of what he learned, Jackson said, is not to snitch on others, including the second person involved in the attack on Emanuel’s son.

“My grandson’s not gonna rat on that guy, so he took the fall,” she said.

• • •

The police say Payne has refused to give up his accomplice in the Dec. 19, 2014, mugging, which happened around 10 p.m. as the mayor’s son was talking on his cellphone not far from the Emanuel home’s front door.

The pair approached Zach Emanuel from behind, punched him, placed him in a chokehold and took off with the phone after demanding he give them the code to unlock it, the police have said. Zach Emanuel, shaken by the mugging, was treated at home by a family doctor.

The police were able to bust Payne because the stolen phone, subsequently sold online, didn’t work. So it was brought to a store, where the serial number turned up the name of the original owner, the mayor’s son, in a stolen-phones database. Investigators said they traced the phone to a man who said he got it from Payne.

Police on the porch of Mayor Rahm Emanuel's home after the attack on the mayor's son on Dec. 19, 2014. | Sam Charles / Sun-Times

Police on the porch of Mayor Rahm Emanuel’s home in Ravenswood after the Dec. 19, 2014, attack on the mayor’s son. | Sam Charles/Sun-Times

On Friday, police spokesman Anthony Guglielmi described the robbery as “a crime of opportunity facilitated by the fact that the victim was unaware of his surroundings because he was talking on his cellphone.” He also said “the victim and Phil Payne did not know each other and had no contact prior to Payne and his accomplice assaulting him that night.”

“They didn’t know who he [Emanuel’s son] was, and they crossed paths,” is how Payne’s grandmother put it.

Payne doesn’t want to talk about the crime. “I thought that whole situation was behind me,” he wrote in a letter from jail, declining an interview request. “I know what I did was wrong and I apologized to the family already.”

The police have declined to release most records on the case, citing the ongoing investigation and the fact that Payne, like Zach Emanuel, was 17 when the robbery occurred.

Now, Payne is an adult under the law, meaning he could spend years in prison if convicted of the two sets of felony charges pending against him.

• • •

Stephanie Kemen, a private criminal-defense lawyer, withdrew from his cases last month, citing an “irreparable breakdown of the attorney-client relationship,” records show. Payne is now being represented by Nicolette Katsivalis, an assistant Cook County public defender, who declined to comment.

According to police and court records, Payne and his brother, who would have celebrated his 28th birthday last Monday, are members of a Black P Stones gang faction centered around Sunnyside and Magnolia in Uptown, two blocks from Payne’s family’s old apartment and a 20-minute walk from Emanuel’s house.

The police beat that includes the P Stones turf — bordered by Broadway to the east, Montrose to the south, Clark to the west and Lawrence to the north — has seen increases in robberies and homicides the past three years, including three killings last year and five so far this year, according to city records.

Some of the violence is the result of rival gangs taunting each other on social media and battling over drug sales throughout Uptown, according to Guglielmi, the police spokesman.

Besides Payne’s brother, the gang casualties this year include 20-year-old rapper Shaquon “Young Pappy” Thomas, a member of a Gangster Disciples faction who was killed in May — a week after he starred in a YouTube video called “Shooters.” In the video, which has more than 2.1 million views, Thomas taunts rival gang members, telling them “you don’t even know how to shoot,” among other things.

Payne, whose gang is affiliated with Thomas’, posted Thomas’ picture at the top of his Facebook page after his death.

Another casualty of the gang violence is 28-year-old DeMarcus Adams, a Black P Stone gunned down in February.

BoShaun Jackson, Payne’s brother, was arrested in May 2014, after the police spotted him hanging out with Adams. Jackson was on parole and not allowed to be in the company of other known gang members.

That’s one of nearly a dozen arrests on Jackson’s rap sheet, which also includes prison terms for illegal gun possession and dealing cocaine.

In the 10 months since turning 18, Payne already has four arrests as an adult.

• • •

Though the brothers have different fathers and were born nine years apart, they were close, with “Bo” serving as a father figure for “Peejay,” their grandmother said.

The two lived with their mother, Nora L. Payne, in an apartment in the 4400 block of North Clifton, records show. She appears to have left the neighborhood since her older son died and her younger son got locked up. Attempts to reach her were unsuccessful.

Loretta Jackson, who is Nora Payne’s mother, said her daughter has battled alcoholism for years. The addiction hurt their relationship, with Loretta Jackson playing only a limited role in helping with her grandchildren, including a third child who is about a year older than Phillip.

“She threw her kids off on BoShaun,” who began getting involved in gang activity when he was about 10, Loretta Jackson said.

With the exception of a few years when Phillip and his sister lived with their father in California, BoShaun became Phillip’s role model.

Loretta Jackson described both as athletic. Though he stood only 5-foot-6, Jackson was a weight-room regular — a solid block of muscle at 157 pounds. His grandmother, who stands roughly the same height, fits perfectly into two pairs of her grandson’s shoes, which she wears occasionally when running errands around her senior housing apartment in Bronzeville.

BoShaun Jackson, Phllip Payne's older brother, was shot and killed on April 30. Facebook photo

BoShaun D. Jackson, Phllip Payne’s older brother, was shot and killed on April 30. | Facebook photo

At 6 feet and 140 pounds, Payne was a good basketball player, his grandmother said. And he got good grades — which Judge Wolfson took note of when she sentenced him to probation on March 9 and had him apologize to the mayor’s wife, Amy Rule, who was in court on behalf of the Emanuel family.

Shortly after that, things began spiraling out of control for the brothers.

On April 3, Payne was arrested with drugs, records show. Responding to a call about trespassers at a Chicago Housing Authority building in the 1200 block of West Leland, officers said they saw Payne and three others enter and leave a third-floor apartment in which Payne was “seated on a couch with a mini-table in front of him with several small blue baggies and a clear plastic bag” containing cocaine. A judge released him on $10,000 bail.

When a blog — Crime in Wrigleyville + Boystown — posted his mugshot and a short story about the arrest online, Payne lashed out on Facebook. He posted the mugshot and the story on the social-media site and taunted the cops, writing, “So what yall. Gon post my every arrest cpd . . .”

Six days after Payne’s arrest, the police pulled over his brother, driving a Mercedes-Benz in the 7500 block of South Halsted, for not wearing a seat belt. As officers approached, they said they saw Jackson pop something into his mouth. He later spit out seven knotted baggies filled with what they said appeared to be cocaine.

Jackson, 27, was charged with felony drug possession. He, too, posted bail.

Less than a month later, he was dead.

• • •

Around 3:30 a.m. on April 30, Jackson was shot while driving on North Lake Shore Drive between Montrose and Lawrence. The bullet went through his left arm into his chest.

He called Payne on his cellphone and was able to drive himself to Weiss Memorial Hospital, crashing his car into a sign near the emergency room, according to the police. But Jackson died four hours later, after being transferred to Illinois Masonic Medical Center.

Payne said little to the police about the shooting, which remains under investigation.

“The victim’s brother relayed to the police that the victim was driving northbound along 4400 N. Lake Shore Drive when he was shot,” according to a Cook County medical examiner’s report. “Victim or brother would not provide any additional information. No offender was named by the victim or victim’s brother.”

The shot came seemingly out of nowhere.

“There was no evidence of close-range firing on the body,” according to the medical examiner’s autopsy report, which also noted that “several baggies containing possible narcotics were recovered from (Jackson’s) mouth, throat and esophagus.”

After his brother’s death, Payne’s Facebook posts veered from sadness to anger to seemingly vengeful.

“Ion wanna talk to nobody please don’t call or text me,” he wrote the day his brother died.

“I can’t take it yall I fell like a lost soul ion know which way to go,” he wrote the next day.

But on May 12, the same day he asked Facebook friends if they needed information about his brother’s funeral, he also appeared to want revenge for Jackson’s death, writing: “I honestly don’t give AF them n—as dont put no fear in my heart. [I]f u shed blood like me then u better be ready for war cause I’m riding for mines.”

After the funeral, he posted a group photo in which he appears to be pointing a handgun at the camera alongside more than a dozen other young men holding pistols and flashing what appear to be gang signs.

Phillip Payne (far left) appears to be holding a gun in this photo he posted on Facebook after his brother's funeral. Facebook photo

Phillip Payne (far left) posted this photo on his Facebook page after his brother’s funeral. | Facebook photo

• • •

Incendiary posts are common in gang culture, sometimes with fatal results. A backlash over comments posted on Facebook in the wake of rapper “Young Pappy” Thomas’ death, for instance, led to the shooting of a 22-year-old man by a gang member just days later, court records show. The man who posted the comments, Clifton Frye, died in June. Germel Dossie, 17, allegedly shot Frye in Rogers Park because of what he’d written. Dossie, charged as an adult, has pleaded not guilty to murder.

Frye’s death is one of 438 murders in Chicago as of early December, up 15 percent from the same time last year, when the number of killings was the lowest it’s been since 1965. The city also has seen 2,258 shootings as of early December, up 18 percent from the same time in 2014.

“Our violent-crime problem in Chicago has become more unwieldy,” U.S. Attorney Zachary T. Fardon said in a speech to the City Club of Chicago in September. “We’re seeing more and more indiscriminate shootings, social-media spats leading to spraying bullets, and often with kids on either or both sides of the gun.”

The month after Payne’s Facebook warning to “be ready for war,” he was locked up after the police spotted him in a stolen car. According to a police report, he told investigators: “I borrowed the vehicle from a crack head about a week ago in return for three bags of crack” and “Yea, I guess I knew the vehicle was stolen.”

On June 23, a judge ordered Payne jailed on $75,000 bail.

Loretta Jackson prays that her grandson can get out of jail, move far away from Chicago and get “the schooling that he needs” to turn his life around.

“I feel very bad. These kids, they never had a chance,” she said of her grandsons. “I just wrote a letter to the president of the United States and asked him to help us. I also had written a letter to Rahm Emanuel’s family and apologized for what my grandson had done.”

The tattoos on Payne’s left arm hint at how hard it might be for the teen to leave gang life behind. One of them, a tribute to his late brother, reads “RIP Bo,” records show.

The other has a five-point star. “Gang,” it reads.

A tattoo memorializing Payne's late brother, BoShaun D. Jackson, it etched on his left arm. Facebook photo

A tattoo memorializing Payne’s late brother, BoShaun Jackson, is etched on Payne’s left arm, according to police records. “RIP Bo,” it reads. | Facebook photo