Feud between Florida rappers Kodak Black, Jackboy leads to fatal shooting, 13 arrests. What we know

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Just over a year ago, a drive-by shooting in Sanford related to a rapper feud left six women injured. One of them, Princess Tolliver of Tallahassee, died from her injuries.

On Monday the Seminole County Sheriff's Office announced that 13 suspects have been arrested in connection with the shooting and charged with murder and attempted murder charges along with other felony charges including racketeering, Sheriff Dennis Lemma said during a press conference, and another remains at large.

Seminole sheriff's detectives believe that "the likely motive for the incident" is a "high profile, very public dispute" feud between Florida rappers Jackboy and Kodak Black, Lemma said. Jackboy's entourage was leaving Sanford in two vehicles, an SUV and a Mercedes-Benz Sprinter van. The shooters fired at the trailing van, believing he was there, Lemma said, but he escaped injury in the SUV.

Here's what we know.

What happened in the 2023 drive-by Jackboy shooting in Sanford?

Jackboy performed at The Barn, a bar and musical venue in Sanford, on Jan. 16, 2023, and afterward left for Orlando with his entourage in two separate vehicles, Lemma said, an SUV and a Mercedes-Benz Sprinter van. Deputies in the area heard gunshots around 2:20 a.m. and saw the drive-by attack from a caravan of six vehicles happen.

"They observed several vehicles at the intersection of (County Road) 46-A and Rhinehart Road and witnessed multiple gunshots being fired toward the Sprinter van of what appeared to be coming from a dark-colored 4-door passenger vehicle," Lemma said. Deputies successfully blocked a black Nissan they said was also involved and trying to get away.

"A subsequent search of that vehicle yielded numerous .223-caliber armor-piercing rounds which matched the caliber of the cartridges later found on the roadway where the shooting occurred," Lemma said.

Princess Toliver
Princess Toliver

Meanwhile, the driver of the Sprinter van drove directly to the hospital. There were 13 people in the van and six of them, all women, had been injured in the shooting. Princess Aura Tolliver, 31, of Tallahassee, later died.

Who was responsible for the Florida Jackboy shooting in 2023?

All of the suspects were members of a well-known street gang in Seminole County called OTF ("On Top Forever"), which is a branch of the national street gang Crips, the sheriff said.

Who is Kodak Black?

FILE - Kodak Black arrives at the MTV Video Music Awards at The Forum, Aug. 27, 2017, in Inglewood, Calif. A Florida judge ordered rapper Kodak Black to drug rehab for 30 days on Tuesday, Feb. 28, 2023, after he allegedly tested positive for fentanyl while awaiting trial on a drug trafficking charge. (Photo by Jordan Strauss/Invision/AP, File)
FILE - Kodak Black arrives at the MTV Video Music Awards at The Forum, Aug. 27, 2017, in Inglewood, Calif. A Florida judge ordered rapper Kodak Black to drug rehab for 30 days on Tuesday, Feb. 28, 2023, after he allegedly tested positive for fentanyl while awaiting trial on a drug trafficking charge. (Photo by Jordan Strauss/Invision/AP, File)

Born Dieuson Octave in Pompano Beach (later changed to Bill K. Kapri) and performing as Kodak Black, the rapper hit No. hit No. 3 on the U.S. Billboard 200 and No. 2 on the Top R&B/Hip Hop Albums chart in 2017 with his debut album, "Painting Pictures," and a single from it, "Tunnel Vision," made the top ten in the Billboard Hot 100. His second album, "Dying to Live," shot to #1 on the Billboard 200 and featured the hit single "Zeze."

Black has been nominated for BET Hip-Hop Awards' best New Hip-Hop Artist, Billboard Music Awards' Top New Artist, the Grammy's Best Rap Song (for "Bodak Yellow," shared with Cardi B.) and MTV Video Music Awards Best New Artist. He's considered one of the biggest rap artists to come out of Florida.

He has also been in trouble with the law since he was young. Black has told interviewers he was kicked out of school for fighting in fifth grade, and was arrested for carjacking in middle school. His third album, "Bill Israel," was released while he was in federal prison for weapons possession.

In 2016, Black was arrested in Hallandale Beach and charged with possession of a weapon by a convicted felon, possession of marijuana, and fleeing from officers. A month later Black was arrested in Broward County and charged with armed robbery and false imprisonment. After pleading no contest and getting house arrest and probation, it was discovered he had outstanding warrants for a rape charge from South Carolina and one for misdemeanor marijuana possession from St. Lucie County. Since then he has been charged with child neglect, more marijuana charges, firearm charges and others.

In 2019, Black was sentenced to 46 months in federal prison after pleading guilty to weapons charges stemming from an arrest at the Canadian-American border. Former President Donald Trump pardoned Black along with 142 other people in his last days in office.

In April 2021, Black's security guard was shot and seriously injured outside a Tallahassee McDonald's where the rapper and his crew were getting food. Black was arrested again on New Year's Day in 2022 for trespassing in South Florida. Barely a month later, two men were injured in a shooting after Black performed at a Tallahassee nightclub.

Most recently, Black was arrested in July 2023 and ordered to drug rehab after testing positive for fentanyl while awaiting trial for a 2022 charge of trafficking in oxycodone. He was arrested again in December 2023 in Plantation for possession of cocaine and tampering with evidence.

Who is Jackboy?

Pierre Delince, 26, who performed under 1804 Jackboy and now just Jackboy, was born in Haiti but lived in several South Florida cities after his family moved to the U.S. in the early 1990s. While living in the Golden Acres public housing project in Pompano Beach, he met Octave, later to become Kodak Black, and they became nearly inseparable.

Jackboy also was arrested multiple times as a minor and an adult for credit card fraud, aggravated battery and armed robbery, even spending nearly four years in juvenile detention between the ages of 13 to 17. According to Urban Dictionary, a "jack boy" is someone who commits robberies.

He began freestyling — a style of improvised verse — and appeared on a popular 2014 song by New York rapper Bobby Shmurda. Kodak Black, who was fast becoming a rising star, gave him a shoutout when asked about other promising rappers and Jackboy began working more seriously on his craft, between other arrests and more jail time. His first mixtape, "Stick Up Kid," featured Black and fellow Florida rapper PnB Rock.

Jackboy's first album, "Jackboy," hit the Billboard 200 at No. 96 and his own rise in fame began. He joined Kodak Black's label, Sniper Gang, and released more albums.

He's also been targeted in another shooting since the Sanford drive-by, police said.

In December 2023 a 27-year-old man was shot in Jackboy's Port St. Lucie neighborhood and online speculation ran wild, saying it was him. Afterward, Jackboy appeared on Instagram Live, smiling and lifting his shirt as he sang to show unmarked skin. Rumors changed to say the victim was Jackboy's brother, but this has not been confirmed. Port St. Lucie police Sgt. Dominick Mesiti said they believed Jackboy was the intended target. A second man was later arrested in connection with the shooting.

Why are Kodak Black and Jackboy feuding?

Depends on who you ask. The story has changed back and forth over the years, but the two began falling out in 2020 after Black went to prison for firearms possession, according to hotnewhiphop.com. He began posting social media shots at an old collaborator, NBA YoungBoy, and accused him of being an informer. Jackboy took his side and also called out YoungBoy, but when Black was pardoned and released he seemed to blame Jackboy for the feud.

The two exchanged cryptic social media posts hinting at tensions. Black repeatedly complained about ungrateful people, Jackboy shared lyrics from Kevin Gates' song "Vouch" about a label ripping off an artist, Black claimed that that he wanted to collab again but that Jackboy had sued him, Jackboy said it was a countersuit, Black sparked online outrage by posting videos of himself throwing $100,000 off a boat and flushing more cash down a toilet, saying that he'd been loyal to someone while failing to see the "signs." He also posted to Twitter about disloyal friends.

After the 2021 death of Florida rapper WizDaWizard Black reached out, apparently to reconcile, and said in a 2022 interview that there was still "genuine love." In an interview of his own months later, Jackboy said he never started the beef but believed Black couldn't be happy for him unless he was credited for Jackbot's success. "I feel like bruh super love when I do good but it gotta be like you helped me to do good," he said.

Jackboy issued a challenge in December 2022 to box Black for $2 million. Black commented on one of Jackboy's Instagram Live sessions in August 2023, saying "You stole outta Sports Authority and went to juvie came home a gangster,” and “I made you.” Jackboy pinned one of the comments, apparently amused.

Was Kodak Black responsible for the Florida Jackboy shooting?

Lemma said he didn't believe the gang members were paid for the shooting and there was no evidence that Kodak Black had any arrangement or involvement with the incident. He said the shooters probably did it for street cred.

"It was clear that they were watching the very public debate between Kodak Black and Jackboy which was not only playing out on social media and in other forms of entertainment media but also in the court system," Lemma said, "and probably took this as an opportunity to make a name for themselves working in this space."

This article originally appeared on The Daytona Beach News-Journal: Kodak Black, Jackboy feud fueled drive-by shooting that killed woman