I was supposed to talk with Chicago-born rapper Dayvon Bennett, aka King Von, but never got the chance before he was gunned down earlier this month outside an Atlanta nightclub.
It’s not every day that a reporter with a background in both crime and pop culture gets a chance to interview someone seen as both a fast-rising hometown rap star and a coldblooded killer. His music had hit the Billboard Hot 200 before his death, but several of his singles, including “Take Her to the O,” hit the Hot 100 posthumously.
I wanted to hear from Bennett’s own lips whether he felt he could escape his hard upbringing and forge a new life. Did he have any regrets? What advice did he have for talented young boys growing up in his old neighborhoods?
Bennett was the boogeyman of Chicago’s drill rap scene who had taken this adapting music world by storm. His real-life activities held the attention of millions of young fans, as well as local and federal law enforcement.
Barely 26 years old, the South Side native and father of two had long been a reputed Black Disciples gang member rumored to have been a young triggerman against rival Gangster Disciple factions, according to police sources.
It was a reputation Bennett himself cultivated in numerous raps and cryptic social media messages that many fans, and some people who work in law enforcement, believe was rooted in truth.
At 23, he was acquitted of murder and attempted murder after an Englewood house party shooting left a man dead. Since then, Bennett was linked to crimes in other cities, including a shooting last year where a 23-year-old man was shot and his possessions taken.
Following his release from jail, Bennett was signed to the Only The Family music label by mentor and fellow Chicago rapper Lil Durk.
In a world of music studio tough guys, Bennett was a cut above. Though he had no prior rap experience, he had a unique and captivating storytelling style — along with his popular first-person translations so that old squares like me can follow along — that could be both plainly stated and witty. His rhymes allowed listeners to understand his head-on-a-swivel mentality. Headlines in this paper often confirm his take: In Bennett’s world a routine trip in the neighborhood could turn into a deadly ambush.
In a new musical landscape where music streams have replaced album sales as metrics for success, Bennett’s biggest hits — “Crazy Story” and “Take Her to the O,” a raw moment-by-moment telling of a sexual pursuit-turned-shootout — each racked up millions of views before his death.
He was a rap prodigy who excelled at freestyling — spontaneous, clever rhyming verses that make sense in context (think Eminem in “8 Mile”) — and was a world-class troll who gleefully celebrated the deaths of rivals online, including the unsolved summer slaying of rap rival Carlton Weekly, or FBG Duck, outside a Gold Coast business.
He was part 50 Cent, part Al Capone, if Al Capone released threatening jazz rags about adversary Dean O’Banion.
But if he was the killer many thought him to be, he was a charming one who smiled more than you’d think a remorseless killer might. His reputation was fierce, but somehow he was able to be a silly online presence of the kind you find on TikTok. In online posts he cuddled with girlfriends and played with his toddlers.
While early artists only portrayed gang members and shooters, many of Chicago’s drill rappers are real-life gang associates and alleged shooters, and some are still in their teens. That means young people far outside Chicago, in the suburbs, in middle America, in London, are partying to blood, revenge and murders of people like real-life Chicago homicide victims Shondale “Tooka” Gregory, 15; Odee Perry, 20; Joseph “Lil Jojo” Coleman, 18; and Leonard “LA Capone” Anderson and Gakirah Barnes, both 17.
Through drill, fans can follow the goings-on of Chicago gang strife like they would a soap opera or reality TV.
To prepare for the interview that would never happen, I consulted with my nephews, ages 20 and 23, whose generation is attuned to the web, seeing new songs, fads, rumors, crimes and even murder footage light years before anyone over 40 or in traditional media.
At their suggestion, I looked up “King Von” on YouTube and fell down one of those spiraling internet rabbit holes of social media creators breaking down his life the way fantasy creators broke down “Game of Thrones” storylines.
I was surprised to find one YouTube narrator, a young man with a British accent, giving his viewers a detailed rundown of Chicago’s gang layout, Bennett’s rivalries with other rappers, and speculation on Bennett’s suspected killings (with numerous Tribune breaking news stories cited as sources).
While it’s not the same musical powerhouse it had been during its heyday of gospel, jazz, blues, soul, rock and house music, Chicago is still a fertile ground for up-and-coming rappers, deejays and producing talent that has birthed a diverse array of artists from Common and Kanye West to Chief Keef and Jarad “Juice Wrld” Higgins, who died last December of a drug overdose.
I’ll never be able to ask King Von whether he ever saw a light at the end of the tunnel. But more than anything, I wish I could have gotten some insight into how communities and the city itself might be able to extract talent from gifted but troubled boys stuck in rough neighborhoods before the harshness of our streets turn them into next King Von.
wlee@chicagotribune.com
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