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Chicago and the struggle for hope

Philando Castile. Alton Sterling. The Dallas and Baton Rouge police officers: A summer of horrific gun violence that continues daily from Orlando to Milwaukee is prompting athletes and activists across the country to ask themselves what can be done. This week, The Undefeated looks at some of the issues involved and holds a town hall discussion in Chicago, the site of some of the nation’s worst gun violence.


It’s the first day of school at Johnson College Prep, and Demacio Bailey is making his rounds, hugging and dapping up friends and teachers at the South Side charter school whom he hasn’t seen since May.

The people in these halls are family. This academic environment challenged him, and Demacio responded by emerging as an honor student. The gym, just to the left of the main entrance, is where he worked himself to exhaustion playing basketball most days this past summer, putting in so much time and effort that his coach expected him to start as a junior.

Tall, good-looking and athletic, Demacio was positioned to be a big man on campus at JCP this year.

Yet two weeks ago, on the first day of the new school year, Demacio had had enough.

“I didn’t feel comfortable,” he said with a notable sigh the day after he made his decision. “I needed something new. I needed a restart.”

Who needs a restart at 16? Why abandon a charter school setting celebrated for its structure to attend a public school where kids might be more at risk? Why jeopardize a major role playing basketball — a game he loves more than any activity in his life — by transferring to one of the nation’s most successful high school basketball programs, Simeon Career Academy, where Demacio is a long shot to make the team?

To an outsider, the decision might seem perplexing. To Demacio, the choice was easy.

“It was too hard to keep walking the halls there without my twin.”


Delores Bailey smiles as she enters the dining room of her home cradling four photo albums in her arms. “These are pictures of the boys,” she says while placing the albums on the circular dining room table.

Opening one of the albums, she begins to turn the pages. There’s a picture of the twins, Demacio and Demario, wearing caps and gowns at their middle school graduation. In another, the twins are smiling widely, ready to pounce on the birthday cake in front of them.

Delores stares long and hard at one page, then begins peeling a photo from the clear, sticky plastic holding it in place. Carefully, she removes the picture of the twins as infants: Demacio lying on his back, and Demario lying on his front, covering his brother with his right arm.

“This is my favorite picture,” Delores says as her eyes well with tears. “All his life, Demario had been covering his brother.”

Delores cries. Demacio, standing by her side, follows. The symbolism of the photo — of Demario covering his twin brother — brings both Delores and Demacio back to the tragic events of the past December.

Demario Bailey cuddles his brother Demacio while older brother Demonta looks on.

Demario Bailey cuddles his brother Demacio while older brother Demonta looks on.

Courtesy Delores Bailey

The day began with the twins walking into their mother’s bedroom in their rented home in the Greater Grand Crossing area and Demacio handing her his cell phone.

“Here’s what we want for our birthday.”

Delores squinted while looking at the new Jordans on the small screen. “Nice,” she said as she turned her gaze back to her sons.

She smiled.

On the eve of their 16th birthday, Delores was incredibly proud of what her sons had become. Respectful kids who were always praised by adults. Great students, each on the honor roll. They were tall (6-foot-2), handsome boys, and Delores knew she’d have to keep them even-keeled with all the attention they were receiving from the girls at school.

She smiled because, deep down inside, Delores knew her twins (she has two other sons, ages 19 and 3) were going to make it. They would escape from “Chiraq,” the name attached to Chicago for the dangerous “war zones” that make up large portions of the city and the place where the twins’ father, Lonnie Seals, lost his life to gun violence after an argument with a friend in 2000.

Delores, who works as a waitress, established rules to assure the twins would have a chance to survive: No mass transportation. No excursions with friends. No walking to the park. No leaving the immediate vicinity of home.

In the suburb of Evanston, 10 miles north of downtown Chicago, that might be called “overly protective.” In Greater Grand Crossing and the surrounding communities 10 miles south of downtown, that’s called “keeping your babies safe.”

After seeing Demacio’s shoes, Delores asked Issy — that’s Demario’s nickname — to see his. “I’ll show you when I get back,” Issy said while leaning over to playfully rub the stomach of his mother, who was on bed rest with a hernia. Then the twins hugged and kissed their mom and left for Demacio’s basketball practice in nearby Englewood.

With Delores unable to drive, they took the city bus to school just 2 miles away. As they traveled north on State Street, they discussed plans for their big birthday just three days away.

Delores’ phone rang within an hour of the twins’ departure.

“Ma,” Demacio blurted.

“What’s going on, Boo?”

“They tried to rob us …”

“Where Issy at?”

“Right here. Issy been shot.”

“What you talking about?”

“We were walking to school, and they shot Issy.”

In a dark underpass less than half a mile from the twins’ school, a bullet fatally ripped through Demario’s chest, just above the heart, as he defended his brother from four teenage robbers. He was covering his brother for the last time.


Demario was murder victim No. 399 last year in Chicago, a city in which 435 people were killed in 2014. That was the most murders in any city in the country. Even as many cities experience dramatic increases in murders in 2015 (murders in Milwaukee are up more than 70 percent from 2014, for example), Chicago, with 341 through Sept. 8, is poised to lead the nation in murders for a fourth straight year. Recently, the city experienced its deadliest day in more than a decade: Nine people in Chicago were shot dead Sept. 2.

But the raw numbers don’t tell the story of the Second City and its second city. The numbers don’t speak of the violence in Chicago being concentrated in specific neighborhoods and leaving residents living in fear. The numbers don’t reveal the tens of thousands of young people in Chicago — good kids such as Demacio — who live lives of forced imprisonment, with their parents trying to shield them from the gang activity and violence that overwhelm some neighborhoods.

“There is an inequality of violence in Chicago,” said Daniel Kay Hertz, who conducts research on the city for the think tank group City Observatory. “There are neighborhoods in Chicago that have not had a murder in over three years. Then you have neighborhoods where parents are afraid to have their kids play outside or walk to the store.”

Demario was one of those kids. Shot at approximately 12:40 p.m. Dec. 13, 2014, Demario died while the Rev. Al Sharpton was addressing a crowd of thousands protesting the deaths of Michael Brown, Eric Garner and Tamir Rice at the hands of law enforcement.

Black lives matter.

Demario Bailey’s life should matter.

Demacio Bailey (22) in action against Bulls College Prep on February 14, 2015.

Demacio Bailey (22) in action against Bulls College Prep on February 14, 2015.

Worsom Robinson


A few months after Demario died, Delores Bailey drove Demacio to a family gathering at a Golden Corral restaurant in Tinley Park. As the car got closer to the suburb just beyond Chicago’s South Side, Demacio’s eyes grew wider. The sights outside the window stunned him. Beautiful and spacious single-family homes. Immaculately cut grass. Most amazingly, kids and teenagers walking freely and playing. No apparent worries.

“It was peaceful,” Demacio recalled. “I thought, ‘If we lived here, Ma wouldn’t have second thoughts of me going out and having fun.'”

Twenty-two miles. That’s the distance that separates the Greater Grand Crossing neighborhood where the Baileys live from Tinley Park, a desirable suburb just south of the Chicago city line.

Those 22 miles might as well be 22,000 miles.

In Tinley Park, people shop at farmers markets and sip coffee at outdoor cafés. The sense of community is high, and crime is low in a village named “the best place in America to raise your kids” by BusinessWeek in 2009.

In Greater Grand Crossing, you’d be hard-pressed to find an outdoor café.

The main commercial street five blocks south of the Baileys’ home, 79th Street, is so notoriously violent that the Chicago Homicide Watch website dubbed the stretch “Murderer’s Row” for the number of lives lost there in recent years. The victims include high school teacher Dr. Betty Howard, who was struck by a stray bullet that penetrated a wall as she sat in a real estate office on the strip last year.

“My boys could never go to 79th Street because of the gangs hanging on the corners,” Delores said. “It’s a shame that you can’t send your kids to a store because it’s not safe. But my kids weren’t allowed to go anywhere.”

Delores established her rules early, beginning the moment she took her sons — the twins were about 6 — to a park near the Ida B. Wells Homes, the housing project where she grew up, and watched them get pounced on by a group of boys who tried to steal their ball.

Delores nearly caught a case.

“I couldn’t believe they would do that,” she said. “I got them away from there and never took them back.”

That began a life of partial isolation. When the boys — the twins and their older brother, Demonte — wanted to play, Delores would pack sandwiches and drive around Chicago until she found an empty park.

Shielded from outsiders, the boys had each other. They did many things together, despite having different interests. Demacio has enjoyed sports, particularly basketball, for as long as he can remember. He remembers those days at the park perfecting his dribbling and shooting skills. Demario, trying to follow his brother’s lead, would scream, “Hey, you’re going too fast.”

For Demario, sports were a challenge. When he was just 2, an eye exam revealed the need for corrective lenses, and he began wearing thick glasses. Despite this, he tried to hang with his twin on the basketball court. But one day at a basketball camp, he decided enough was enough.

“Man, I’m tired,” Issy told the camp’s coach as he walked off the court. “This basketball thing is for Demacio.”

In lieu of sports, Issy became a fashion aficionado. He rocked white outfits from head to toe, including white shoes. He was flashy with upscale taste, and one of his prized possessions was a big-buckled Ferragamo belt he bought for $300.

The girls loved his style. And Issy loved the girls.

“My class is in the weight room, and he’d come in every day to check himself out,” said Rachel Terry, an advisor at Johnson College Prep. “He’d look in the mirror, check his hair and glasses, and then say, ‘All right, Miss T,’ and he’d walk out.”

When Demacio suited up for the JCP basketball team — friends describe the now 6-foot-4 forward as a look-alike to Chicago Bulls guard Jimmy Butler — Demario was the loudest fan in the gym.

“It always made me feel good to look up in the stands and see him cheering for me,” Demacio said.


Whereas many kids their age loathe school, the twins were just the opposite. To them, school was much more than an education. It provided social interaction, recreation, freedom and their ticket out of Chicago, all wrapped neatly into one 10-hour package.

They arrived on time and were rarely absent. They were respectful and excelled in the classroom. They knew Johnson College Prep’s first graduating class in 2014 had a 100 percent college placement rate, and continuing their education was something they aspired to.

They’d surf the net at night to look at colleges. They wanted warm weather, so Florida and California made their short list. When they discovered UCLA’s website, the twins fell in love with what the campus offered: sunshine, safety and hope. UCLA and Johnson College Prep, prestigious academic institutions located in Westwood and Englewood, respectively, represented differences seemingly as vast as heaven and hell.

“It seemed like a great place to have a lot of fun and learn,” Demacio said. “And it seemed like a place where nothing bad happened.”

The twins had had enough of bad. They were tired of living in fear and hearing about friends getting jumped and assaulted. They wanted a life far away from Chicago, and they wanted to never look back.

“We were scared to go anywhere by ourselves,” Demacio admitted. “Gangs are a big problem, and if Mom keeps on you about staying home, there’s a reason. But it was hard. We’d see everybody else outside having fun, and we just wanted to do the same thing.”

Last year, Delores moved the family into a five-bedroom home on a block consisting mostly of working class residents. Even though they were not far from the violence on 79th street, Delores felt they had escaped “the hood.” Finally, the twins — then age 15 — were allowed to ride the bikes they received when they were 9. The bikes were small, the boys were tall, and seeing them ride the bikes was like watching a comedy.

Still, Delores delighted in watching her sons navigate their bikes on the road outside her home.

“I thought we had made it,” she said.

Until Dec. 13, 2014.

Having loaned her car to a friend while she nursed the hernia, Delores couldn’t drive Demacio to basketball practice that day. He volunteered to take the bus, and Issy, seeing an opportunity to get out of the house, decided to go along.

Once on the bus, the twins had two options:

Option 1: Take the bus to Marquette Road and walk through various neighborhoods — and gang territories — to Johnson College Prep, a distance of slightly less than a mile.

Option 2: Get off the bus at 63rd Street and walk under a dark viaduct, a distance of about a half-mile that avoided any neighborhoods and lessened the chance of encountering anyone.

Chicago’s young people have to weigh these options every day and hope they choose the right one. The boys chose the viaduct, which was the lesser of two evils in their minds.

“The other way, we’d see boys on the corner, and we didn’t want anyone to bother us,” Demacio says. “We never saw anyone under the viaduct. We felt that was the easiest and safest way.”

The twins had no clue that several armed robberies had already taken place under the darkened tunnel that day. As they entered the viaduct, they could see several people approaching.

“You know they say when something happens, you can feel it in your stomach?” Demacio says. “I felt something was going to happen. We kept walking. And … you know …”

Demacio pauses and bows his head. As tears stream down his cheeks, he is unable to describe what happened next.

Delores Bailey celebrates her boys' graduation from middle school.

Delores Bailey celebrates her boys’ graduation from middle school.

Courtesy of Delores Bailey


The Baileys are not alone in their tears. Outside St. Sabina, a mostly black Catholic church in the Auburn-Gresham area of Chicago’s South Side, there’s a memorial board near the entrance of the church’s youth and recreation center. It is a reminder of the world in which the Baileys live.

More than 100 photos are taped to the board, each representing young murder victims in Chicago. Jonylah Watkins’ picture is there; the 6-month-old was mortally shot in a drive-by while she sat in her father’s lap in a parked minivan. In 2012, a stray bullet cut down Heaven Sutton, 7, not long after she got her hair styled for a trip to Disney World. Tanaja Stokes was jumping rope when she was shot in the head in 2010. In 1998, the beaten and raped body of Ryan Harris was found in a vacant yard in Englewood.

Children in caskets leave the deepest scars. They pull their survivors — as Delores and Demacio Bailey can attest — into an emotional abyss.

Pam Bosley swallowed a handful of Xanax pills on the eve of the one-year anniversary of the murder of her son, Terrell, who was gunned down as he unloaded band equipment at Lights of Zion Missionary Baptist Church in 2006. It was her second failed suicide attempt.

“I got tired of getting up and hurting, of going to stores and passing by the food he liked,” she said. “Our relationship was done. I just couldn’t accept that my son was gone.”

Depression forced her to take a six-month leave from her job at a bank. Her heart broke each night listening to her youngest son, Trevon, pray, “God, can you make sure nobody else gets killed in my family?”

When prosecutors couldn’t convict the man accused of slaughtering her 18-year-old son, Pam plotted his murder. She drove her van around the alleged killer’s neighborhood in search of an opportunity to end his life.

“In my mind, I was going to find him and run him over,” she recalled, with her expression revealing shame. “Fortunately, my father called while I was out looking.”

As her dad talked her down, Pam pulled over and cried uncontrollably.

“I would never, ever do anything like that,” she said. “But when you lose your child, you lose your mind.”

She now shares her agony with other Chicago survivors. She joined “Purpose Over Pain,” a group of Chicagoans who — like Pam Bosley and Delores Bailey — lost children to gun violence. Beyond support for grieving parents, the organization advocates for tougher gun laws.

“We reach out every time a parent loses a child in Chicago,” said Annette Nance-Holt, a Chicago Fire Department lieutenant who lost her son, Blair, in 2007. “But a lot of people find they can’t be a part of this because every time you retell your story, it takes a toll.”

Just as Delores cries in almost every conversation about Demario, you can hear the toll in Annette’s voice as she remembers Blair, a 16-year-old honor roll student murdered on the way home from school while shielding a friend from gunfire on a city bus.

Annette and her ex-husband, retired police detective Ronald Holt, are haunted every day by the death of their only child. They didn’t get to take pictures of Blair and a date at his senior prom or watch proudly as he received a high school diploma. They will never attend a wedding or become in-laws. They will never have the chance to spoil a grandchild.

“At times I say, ‘Damn, I put all that money into braces, and I never got a chance to see his smile,'” Annette said. “There are a lot of things his dad and I won’t get to share. We don’t have a legacy.”

Delores and Demacio Bailey this past summer.

Delores and Demacio Bailey this past summer.

Jerry Bembry/ESPN


The day after Demario Bailey was killed, a Sunday, hundreds of students arrived at Johnson College Prep. The students needed one another in their time of grief and despair.

Two days after Demario was killed, Demacio showed up at school. At a time of loss and devastation, Demacio needed normal.

Johnson College Prep had a basketball game scheduled that Monday night. Coach Ceddrick Hunter was prepared to cancel it, but Demacio convinced Hunter to let the team play. In the locker room following a 23-point loss, Hunter struggled to find the right words.

In walked Delores Bailey.

“She gave this incredible speech about being there for each other, living a positive life and making sure they supported each other,” Hunter said. “This was someone who had just lost a son, and there she is being selfless. It was amazing.”

Demacio’s birthday was the next day, Dec. 16, 2014. Given that he lost his brother three days earlier, the date was hardly a celebration. It was more an acknowledgement of his 16th year.

It was also a somber reminder that his twin, Demario Bailey, would remain 15 forever.

For the first three weeks after his brother’s death, Demacio didn’t sleep in the room he had shared with his brother. Instead, he chose to spend more than a few sleepless nights in the spare bedroom in the basement.

“I was scared,” Demacio admitted. “We had bunk beds, and each night, we’d say goodnight to each other. That wasn’t ever going to happen again, and I just didn’t feel like going up there without my brother.”

The night Demacio returned to the room, he sat in silence for an hour. Every night as he goes to sleep, Demacio tries to forget everything that happened at the viaduct.

With sleep comes amnesia. Waking up brings reality.

“The first thing I do every morning is look at his bed,” Demacio said. “And he’s not there.”

Through all the despair, Demacio continued to thrive in school. On report card day in April, he stood alongside his mother as his advisor, Rachel Terry, revealed his third progress report: 3.1 GPA and perfect attendance again. Rave reviews from teachers again. Honor roll again.

Demacio, wearing his brother’s favorite Ferragamo belt, smiled as Delores looked upward and raised both hands to the sky. “Praise God,” she said. Then she turned to embrace her son. “That’s what’s up, man,” she said. “I’m so proud of you. No excuses. You have not made any excuses.”

As spring break approaches, Demacio has an opportunity for a much-needed escape. An aunt and cousin invite him on a trip to Dallas. Demacio is excited. He has never left Chicago, and the trip presents his first opportunity to fly. But Delores quickly vetoes the idea.

“I just don’t feel comfortable right now. It’s just too early for you to just jump up and leave me here worried,” Delores says while looking at her son. “Right now, I don’t trust nobody. The minute you get comfortable, the minute you get comfortable …”

After Demacio leaves the dining room, Delores expresses guilt about not letting her son travel.

“I feel bad that my son left here and didn’t get a chance to live, and it’s not fair for Demacio to not get a chance to experience life,” she says.

This past summer, Delores showed signs of allowing Demacio a bit more freedom. He left the state for the first time when he visited Kentucky State University with his older brother, and he attended a program for high school students at Penn State.

“It was my first plane ride, and it was a rush,” Demacio said excitedly. “It was nice to look out the window and see Chicago from the sky. I felt free leaving the city. I felt relieved.”

The rest of his summer was spent playing basketball at gyms near his home and at Johnson College Prep with his teammates. Yet even before the first day of school Aug. 25, when he walked the halls and felt a tremendous void without his brother by his side, he had made the decision to leave.

“It just would have been too much to go another school year at that school,” Demacio said. He told his mother his decision after the first day of school. “Me and my twin did everything together there, and to not have him with me, it was just too much for me to deal with.”

Johnson College Prep was, on the surface, comfortable. Simeon brings new challenges, new friendships and new opportunities.

It’s a restart Demacio desperately needs.

“It was tough leaving and saying goodbye to everybody,” Demacio said. “But this is something that I had to do for me.”

Even if that means not playing basketball. Demacio averaged 2 points and 3 rebounds a game for JCP, which plays in a league for charter schools. He is transferring to a national powerhouse, Simeon, which was the top-ranked 4A team in the state when it was upset in the state Super Sectional last season. In the past decade, Simeon has produced two NBA players, Jabari Parker and Derrick Rose.

“Of course, I’d like to play,” Demacio said. “I’ve already reached out to the coach. We’ll see what happens.”

The move to Simeon, where high school basketball star Ben Wilson was murdered in 1984, makes Delores nervous.

“This place is too big, and there are too many kids here,” Delores says nervously as she sits in her car outside the school, waiting to pick Demacio up from playing pickup basketball. “But if this is what makes him happy, I have to give him a chance. He is trying to live his life because he knows that tomorrow is not promised.”

With his summer behind him, Demacio Bailey counts down his remaining summers in Chicago. In his mind, as he begins his junior year of high school, he has two.

In the fall of 2017, he’s off to college — and away from the South Side for good.

“I just want a better life,” he said. “I want to be any place but Chicago.”

This story was originally featured on ESPN.com

Jerry Bembry is a senior writer at The Undefeated. His bucket list items include being serenaded by Lizz Wright, and watching the Knicks play an NBA game in June.