A person walks outside the Cook County Jail processing center at 27th Street and California Avenue in Chicago on July 21, 2022. A year earlier, on July 10, local rapper Londre “KTS Dre” Sylvester was shot dozens of times by gunmen shortly after his release from the jail. (Chris Sweda / Chicago Tribune)

Walking out of Cook County Jail’s intake center that drizzly Saturday night a year ago, Londre Sylvester smelled freedom for all of 100 steps before two gunmen made him the latest example of Chicago’s often grisly street life.

The 31-year-old South Side rapper, who went by KTS Dre and Kutthroat Dreko, had been locked up nearly two weeks earlier for violating conditions of his bail in a gun case.

But the details of Sylvester’s life and that of numerous young men and boys slain on the South and West sides each year are largely invisible to the mainstream, particularly now when it’s consumed with fears driven by inflation, mass shootings, monkeypox, carjackings, CTA holdups and teenage mobs.

One moment, Sylvester — dressed in simple black pants, white socks, white shoes and his court-ordered ankle monitor — was ready for his first nonjail meal in weeks. Hours later, he was on Dr. Michael Eckhardt’s examination table with so many bullet wounds pathologists were forced to count the gunshots in groups.

Sylvester is hardly the first young man to die in a public hail of gunfire, but his ambush outside the jail and courthouse inspired dozens of national and international headlines thanks to three terms that would burn the brightest online: “Chicago,” “rapper” and “64 shots.”

Police photo of Londre Sylvester, 31, who was killed in an ambush outside Cook County Jail in July 2021. ( Cook County sheriff's office)

It may be a surprise to many that glimpses of Chicago’s underworld, its violence and body count, its rogues, hit men and scammers, have become entertainment for millions of young people thanks to the social media age, no doubt aided by the city’s reigning status as a tough town. Zealous young fans eager for beef scan rap songs for obvious threats and cryptic messages that could signal conflict with another rapper or gang set.

Men and boys of color who are powerless and invisible except for their run-ins with police can find the acceptance and love from rap fans — strangers — that elude them in a city that sees them as threats.

Representing the “Kill To Survive” faction of the Gangster Disciples, Sylvester was an up-and-coming rapper and a popular social media presence for young drill rap fans — a stocky, 5-foot-4 street tough known for trolling, bullying and threatening gang opposition on the rough-and-tumble Southeast Side. He was recognizable for KTS’ trademark throat crosshair tattoo.

He and his stepbrother, rapper Devon “KTS Von” Davis, were known for terrorizing their enemies and lyrically disrespecting their dead rivals, a major violation on the street that had led to much bloodshed. Davis was gunned down at age 21 in 2015, and his father, Vincent Davis, was slain the following year.

Though reviled by some Gen X hip-hop purists, Chicago’s drill rap music scene has gained legions of fans because of genuinely gritty, often violent tales and the graphic daydreams of young men and a growing number of young women, behind some of the violence contributing to the city’s death toll.

In a strange irony, teenagers and young adults with legal troubles, hard-fought street reputations and natural rap talent can be plucked from obscurity and become major entertainers. Chicago has launched numerous drill stars, some, according to law enforcement, with gang ties and affiliations, including Keith “Chief Keef” Cozart, Durk “Lil Durk” Banks and Herbert “G Herbo” Wright.

If Al Capone were alive today, he’d be a Chicago drill rapper and very likely a top dog in the music industry as well as Chicago’s underworld. The infamous St. Valentine’s Day Massacre of seven men at a Lincoln Park garage while Capone was chilling in Florida would have cemented him as a street legend.

I didn’t want the Tribune’s initial “64-shot” news story and the wire articles written off of it to serve as yet another hazy stand-alone crime brief that did little but reinforce negative perceptions, one that cynically associates Chicago, crime and rap and does little to offer context. Why was Sylvester killed? What does rap have to do with it? Was he even shot 64 times? Sylvester may have been a terrifying figure to some, but he was still someone’s son.

I started with his autopsy report, which took the medical examiner’s office several months to complete due to the sheer number of wounds. For the record, Eckhardt, the doctor who examined Sylvester’s body, found only 34 entrance wounds, but thanks to dozens of splintered bullet pieces lodged inside his body, he couldn’t determine what bullets exited the body.

In a coldly clinical way, Eckhardt’s post-mortem report describes the intense chaos of his hellish final moments, gunshots crossing and colliding in this body.

“Multiple radiopaque projectiles and projectile fragments within the head, bilateral upper extremities, torso, buttocks and bilateral lower extremities. There are multiple skull fractures and fractures of the right radius and ulna (forearm bones),” the report read.

“Multiple gunshot wounds are in close proximity to each other, such that specific pathways cannot be determined and these will be described as collective groups of gunshots.”

A body diagram in the post-mortem report shows the numerous gunshot wounds suffered by Londre "KTS Dre" Sylvester during a deadly ambush outside Cook County Jail in July 2021. (Cook County medical examiner's office)

The body diagram in the post-mortem report for Sylvester gives the clearest indication of the toll of the attack. Much of the empty space around the body outlines is covered in handwritten notations, lines and information bubbles detailing each visible wound.

One diagram in the report shows two wounds near Sylvester’s crosshair tattoo, each nearly hitting the mark.

Sylvester may not have been shot 64 times, but his death was an ugly, brutal execution even by Chicago gangland standards — one clearly meant to send a message. Sylvester’s killer, it seems, wanted to give him a most disrespectful death. In gangland, multiple gunshots to a victim’s head and face are often indicators of contempt for the enemy, as any fan of mob movies probably knows. The two gunmen left in different cars that went in separate directions; they remain unidentified as police have yet to make an arrest.

Sylvester was no stranger to local law enforcement with 22 arrests since 2008, some for carrying guns illegally, according to police and court records.

YouTube, Instagram and TikTok are hotbeds of speculation about Sylvester’s involvement in homicides and shootings of the rival gang sets, most notably the NLMB gang, but he was never formally charged with killing anyone. In other words, Sylvester was a man with many possible enemies.

Despite the violence associated with drill and the numerous deaths of local rappers during the last decade, the success some of the drill stars are seeing is undeniable. Few rap stars are having the year that former Parkway Gardens resident Lil Durk is having in 2022.

Once associated with fellow “O Block” rapper Keef, Lil Durk has since branched out and launched his own label imprint and branding. Scheduled to perform at Lollapalooza, Lil Durk, 29, is one of the year’s most streamed artists on the Billboard Hot 100 and is playing festivals all over the country and working beside the largest acts. Luxury fashion label Marc Jacobs recently released an ad campaign featuring Lil Durk modeling its clothing and a tote bag just a month after he walked the runway at Paris Fashion Week.

But Lil Durk, an alleged associate of the Black Disciples gang who has been known to dis his dead enemies publicly, remains free on bond after being charged in Atlanta with attempted murder. Recently, the Cook County state’s attorney’s office filed documents objecting to the rapper’s attempts to have his local criminal record expunged and sealed.

Can you imagine a South Side bootlegger during Prohibition becoming a music star, socialite and fashion icon?

Lil Durk’s protege, King Von, who was fatally shot in Atlanta in November 2020, was a prodigious storytelling rap act who frequented the Parkway Gardens housing complex before his rise to fame. He was also linked to unsolved homicides.

The bad news is that our crime problems are likely to continue unabated as root causes of the city’s ills remain. It’s no secret many young Black and brown residents are falling behind in the city’s job market that is increasingly skewing more white-collar than blue. Poor career prospects have led thousands to flee Chicago for greener pastures in the South and neighboring states.

Many who stay and lack the skills or special training often find themselves working in any number of basic, hard-core street rackets and hustles to feed their families, ranging from drug dealing, armed robberies and car thefts to credit card scams. Without a viable career outlook, some are caught in a trap in which crime offers the most rewards. But the spotlight of fame sometimes shines on Chicago’s talented few and instantly dashes poverty, lack of education and criminal status.

Why would Chicago’s violence let up when having a gun, a clever rhyme and a smartphone can instantly make you famous?

Will Lee is a reporter who covers crime and neighborhood topics for the Tribune.