Chicago Drill: The Rise of a Musical Subculture and Its Path of Crime, Violence, and Tragedy

Origins of Drill and Its Ties to Chicago’s Streets

Originating in Chicago, drill rappers have long been linked to legal battles, incarceration, and even tragic deaths. As this hip-hop subgenre gained momentum, the city faced a 38% spike in homicides, driven largely by gang violence concentrated on the South Side.[1] With “drill” as slang for “kill,” the music and its artists often reflected the challenging, crime-heavy realities around them.[2] Explore how rappers like Chief Keef, King Von, and Lil Durk became both central to the drill movement and, for some, symbols of its darker consequences.

Chief Keef: Drill’s Pioneering Star and His Legal Trouble

Chief Keef, a pivotal figure in 2010s drill, brought Chicago’s gritty street life into his hardcore rhymes.[3 ] Starting at 16 with his single “I Don’t Like,” he built a following in Chicago’s high schools, leading to mixtapes, viral videos, and an Interscope deal.[4 ] His debut, Finally Rich (2012), hit the Billboard Top 30.[5] Over the years, Keef released numerous projects, including Bang 3, Thot Breaker, Mansion Musick, and The GloFiles series.[6 ] By 2024, he had collaborated with major names like Kanye West, Mike WiLL Made-It, and Zaytoven, solidifying his prolific influence on the drill scene.[7]

Chief Keef’s legal troubles began in January 2011, when he was arrested for heroin charges and placed under house arrest as a juvenile.[8 ] Later that year, after an altercation with police, he was detained again, facing multiple charges. He continued to face legal issues, including being investigated for potential involvement in rapper Lil JoJo’s 2012 death, which he denied.[9 ] In 2013, a probation violation from a gun range interview led to a two-month juvenile detention sentence, and he faced additional suits for missing performances.[10 ] [11 ] Further arrests followed for speeding, probation violations, and drug-related charges.[12 ] [13] In 2017, he was arrested for assault but charges were dropped, and in 2019 he received a suspended sentence for a cannabis charge in South Dakota.[14 ]

Lil Reese: A Rising Career Overshadowed by Violence

Lil Reese, born Tavares Taylor and a product of Chicago’s South Side, gained Midwest fame with his feature on Chief Keef’s 2012 hit “I Don’t Like.”[15 ] At 19, he signed with Def Jam, who released his Don’t Like mixtape, hosted by DJs Drama and Don Cannon.[16 ] Through Glory Boyz Entertainment (GBE), founded by Keef and Fredo Santana, Reese also released the Supa Savage mixtapes in 2013 and 2015.[17 ]

On November 11, 2019, Taylor was critically wounded after being shot in the neck at a busy intersection near Markham and Country Club Hills.[18 ] Around 2:30 p.m., police responded to reports of a car chase with witnesses hearing up to 12 gunshots.[19 ] The pursuing driver exited his vehicle, fired a small rifle, and then fled the scene.[20 ]

On November 18, Taylor shared that he had been released from the hospital, announcing he had survived the shooting and was “alive and well.”[21 ]

On May 15, 2021, Taylor and two other men were injured in a shootout at a parking garage in Chicago and were taken to Northwestern Memorial Hospital.[22 ] His eye was grazed by a gunshot; he and another one of the men, who was shot in the knee, were later listed in fair to good condition, and the third in critical condition with multiple wounds to the torso.[23 ] The shooting was reportedly over a stolen Dodge Durango.[24 ]

Lil Durk: Musical Success Amidst Legal Struggles

Lil Durk (Durk Derrick Banks) grew up in Chicago’s Englewood neighborhood, raised by his mother while his father served a prison sentence.[25 ]

Lil Durk built a following by releasing mixtapes through his collective, OTF (Only the Family), on platforms like YouTube and Myspace, which led to a Def Jam deal in 2012.[26 ] Durk’s debut album, Remember My Name (2015), hit No. 14 on the Billboard 200. That same year, tragedy struck when his manager, Chino Dolla, was murdered following discussions about an anti-violence initiative.[27 ]

Featuring artists like DeJ Loaf and Yo Gotti, his 2016 album Lil Durk 2X included the Ty Dolla $ign-assisted “She Just Wanna.” Durk continued with projects like Love Songs for the Streets (2017), Signed to the Streets 3 (2018), and Love Songs 4 the Streets 2 (2019), which charted in the Top Five despite his legal issues.[28 ]

In 2023, Durk’s album Almost Healed earned a Grammy for Best Melodic Rap Performance for “All My Life” with J. Cole.[29 ] However, in October 2024, he was arrested on conspiracy to commit murder-for-hire after five OTF members were implicated in the murder of Quando Rondo’s cousin—a retaliatory act for the 2020 murder of King Von.[30 ]

King Von: A Life of Crime and Controversy

King Von, born Dayvon Bennett, grew up in Chicago’s South Side, in the notorious O Block neighborhood.[31 ] By his teenage years, he had become involved in crime and spent several years in and out of jail before finally turning to rap in 2018.[32 ] Von’s captivating storytelling style caught the attention of fellow drill rapper Lil Durk who signed him to his Only the Family label.[33 ] There, Von released his viral 2018 single “Crazy Story,” featured on his debut mixtape, Grandson, Vol. 1.[34 ]

In April 2014, Bennett was questioned as a suspect in the killing of 17-year-old Gakirah “K.I.” Barnes, a Gangster Disciples member, but wasn’t charged due to witness inconsistencies.[35 ] In 2021, unsealed police documents named him as Barnes’ killer.[36 ] Later, in July 2014, he was charged with murder and attempted murder related to a May shooting in Englewood, Chicago, but was acquitted in 2017.[37 ] [38 ] In 2019, he and Lil Durk were charged in an Atlanta shooting but were released on bond; charges against Durk were later dropped.[39 ] In January 2023, FBI files revealed Bennett allegedly placed a hit on Carlton “FBG Duck” Weekly before Weekly’s 2020 murder.[40 ] In October 2024, Bennett’s estate, Durk, and OTF Records faced a wrongful death lawsuit from Weekly’s family, accusing them of profiting from Weekly’s death through misconduct.[41 ]

In the early hours of November 6, 2020, around 2:15 a.m., Bennett and his crew became involved in a confrontation with Quando Rondo’s entourage outside the Monaco Hookah Lounge in Atlanta, Georgia.[42 ] The dispute quickly escalated to gunfire, with Bennett sustaining multiple gunshot wounds that led to his death.[43 ]

Posthumous albums like 2023’s Grandson were released in the years that followed, continuing Von’s dominance of the charts long after the end of his life.[44 ]

Lil JoJo: A Life Cut Short by Feuds and Retaliation

Born Joseph Coleman, 18-year-old rapper and Gangster Disciple affiliate Lil JoJo gained notoriety in Chicago’s drill scene after posting the music video for his song “3HunnaK” on YouTube.[45 ] The scathing diss track was aimed at Lil Reese, Chief Keef and affiliates involved with rival group 300, a faction of the The Black Disciples.[46 ]

On September 4, 2012, Coleman was killed in a drive-by shooting in Chicago’s Englewood neighborhood while riding his bicycle.[47 ]

In the days leading up to the shooting, heated exchanges and threats circulated on social media, especially on Twitter, between Coleman’s associates and rival groups.[48 ] Among these were biting jabs from Coleman aimed at Chief Keef’s crew.[49 ]

FBG Duck: A Life Marked by Loss and Violence

Born Carlton Weekly, Chicago rapper FBG Duck was born in 1993 and raised on the often dangerous south side of the city, and got involved with gangs and street violence at a young age.[50 ]

FBG Duck rose as a member of the rap collective Fly Boy Gang (the source of his “FBG” prefix), which intersected with various Chicago street gang factions.[51 ] Alongside multiple rivalries and a stabbing incident involving a girlfriend, Duck also endured the tragic loss of his older brother, FBG Brick, who was fatally shot in July of 2017.[52 ] The turbulence in his life and the untimely deaths of loved ones became central themes in his mixtapes, including notable releases like Different Personalities (2015), its 2017 sequel Different Personalities 2, and the emotionally charged Look at Me 2 (2018).[53 ]

On August 4, 2020, FBG Duck was fatally shot 16 times near the Dolce & Gabbana store in Chicago’s upscale Gold Coast neighborhood. The 26-year-old’s girlfriend and another man were also injured in the attack.[54 ]

Fredo Santana: A Talented Life Consumed by Trauma and Addiction

Rapper Fredo Santana, born Derrick Coleman, emerged in the early 2010s as a leading figure in Chicago’s drill scene, though he was barely out of his teens.[55 ] He released his debut mixtape It’s a Scary Site in 2012, the same year his younger cousin and Glory Boyz Entertainment co-founder, Chief Keef, made his breakthrough from the South Side.[56 ]

He made waves with his debut album, Trappin Ain’t Dead, featuring Kendrick Lamar, Chief Keef, Peewee Longway and even appeared in Drake‘s music video for “Hold On, We’re Going Home,” portraying a bad guy kidnapping Drake’s “girlfriend.”[57 ]

Unfortunately, Santana became addicted to lean and Xanax to cope with trauma and the loss of his friends.[58 ] In March of 2017, he was as rushed to the hospital after suffering a seizure and was later diagnosed with idiopathic epilepsy.[59 ] After a friend found him mid-seizure, he suffered liver and kidney failure in October 2017.[60 ] Though Santana tweeted about going to rehab, he passed away on January 19, 2018 at the age of 27 after suffering a fatal seizure in his Los Angeles home. According to an autopsy performed by the Los Angeles County coroner, cardiovascular disease was ruled as the main factor leading to Fredo’s death.[61 ]

RondoNumbaNine: A Career Derailed by Murder Charges

Rondonumbanine aka Clint Massey was a fixture in the Chicago’s drill scene, dropping tracks like “Ride” with Lil Durk.[62 ] [63 ]

On March 9, 2014, Rondo was charged as one of two gunmen who shot 28-year-old livery driver Javan Boyd.[64 ]

On February 24, 2014, Massey and Ealy, along with a group, drove to the Wentworth Gardens apartment complex in Chicago to retaliate for a prior shooting.[65 ] Spotting 29-year-old Boyd sitting in a parked car, they approached him on foot and fired multiple shots before fleeing.[66 ] Boyd, who had been waiting for a customer, was later pronounced dead at Stroger Hospital. Massey was linked to the crime through fingerprints on Boyd’s car and surveillance footage.[67 ]

On July 5, 2016, Numba 9 was sentenced to 39 years in prison for his involvement in the 2014 murder of Javan Boyd.[68 ]

[20 ] https://www.tmz.com/2021/05/15/rapper-lil-reese-shot-again-chicago/