Even without the chart-topping singles and alleged baby mamas, YoungBoy Never Broke Again knows how to make a headline. The superstar rapper is almost just as well-known for his run-ins with the law as he is for his emotionally-tormented music, at this point. In fact, it’s part of what kick-started his career in the first place. 

At only 20 years of age, born Kentrell DeSean Gaulden, has amassed a diverse criminal record, which he has partially contested. With his alleged illicit conduct landing him in hot water once again, we’re taking a look at what brought the Baton Rouge, Louisiana native into such a challenging spotlight over the years.

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2015: First Ever Arrest, Robbery 

You may have heard about NBA’s recent arrest last week, but that affair, which will be covered shortly, is a blip on the radar compared to his arrest record. Starting in 2015, YoungBoy caught his first-ever charge. This encounter with the law was the result of him having committed a robbery at only 15 years old. While some Gangsta Rap artists can blur the lines between life and art with their alleged criminal activity, fans can draw a straight line between his first arrest and his introduction to rap. While jailed in Tallulah, Louisiana on this charge, YoungBoy put pen to pad and founded a rap career based off of his troubled life. These early musings would become the basis for what is now his well-known 2015 debut mixtape, Life Before Fame.

Despite an acerbic persona potentially playing into the charges prosecutors pressed against him, YoungBoy spoke of the time during an interview with The Fader in humble terms, saying, “I had been rapping, but I used to hide that shit.” He continued, “I was scared, not for sure ‘bout myself, playing with my craft.” After this six-month period of change and self-discovery, a criminal court judge opted in favor of NBA’s release, allowing him to continue into young adulthood with his freedom intact.

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November 2016: Attempted Homicide

In perhaps the most on-the-nose metaphor for his life’s troubled intersection of work and personal interests, YoungBoy was arrested at a concert at which he was scheduled to perform, on November 28th, 2016. The arrest in Austin, Texas arose over law enforcement’s belief that YoungBoy wildly fired guns into a crowd via drive-by, just weeks prior in Baton Rouge. The arrest occurred at an exceptionally unfortunate time for YoungBoy, who had just turned 17 and was thus eligible to be tried as an adult.

It appears prosecutors were able to paint a vivid picture of possible punishments enough to overcome YoungBoy’s recalcitrant mindset, as he not only paid a post-conviction bail of $50,000 but also accepted a deal to plead guilty and comply with officers in exchange for a less severe prison sentence. Having been charged with two counts of attempted first-degree murder, YoungBoy got off with a steal of only 9 months behind bars and three years of probation– a slap on the wrist compared the maximum of forty years imprisonment he could have received under Texas State law. The prosecutorial reasoning is not fully known at a public scale, so it is undetermined if/how much NBA Youngboy helped prosecutors by providing information on two of the other alleged shooters in the drive-by.

February 2018: The Whole Nine                            

This is where it gets more divisive. While most teens might quiver at the possibility of facing a 40-year prison sentence, YoungBoy showed no displeasure in doubling down in both his musical and criminal careers. His rap success mushroomed as he released more hit songs and successful projects, and even signed to media giant, Atlantic Records.

Despite the groundbreaking success of tracks like “Untouchable,” authorities appear to have remained unimpressed, as he was arrested on a fugitive warrant for having sought to evade arrest on charges of weapons possession, kidnapping, and assault. The latter two chargers pertained in part to an incident recorded in a hotel hallway, which depicts YoungBoy physically abusing his girlfriend, Jania Jackson, then dragging her into a hotel room.

Nonetheless, NBA YoungBoy only remained in jail for one month, until he paid his $75,000 bond. Despite the event having transpired more than two years ago, the couple only split somewhat recently, with NBA having finally gotten a plea deal in December for “simple battery family violence” and an agreement to pay a $1,500 fine and complete an anger-management course. Jackson took to social media when the video was first published, saying the two were only playing, but the public discourse on the matter remains divided.

May 2019: Attempt on His Life 

There was plenty of drama that happened between February 2018 and May 2019, but for now, we’re sticking to what Youngboy caught charges for. And for what it’s worth, the reason he caught a charge was a doozy. It transpired quickly on the morning of May 13th, just outside the Trump International Beach Resort. YoungBoy was reportedly targeted by a shooter for reasons stemming from a beef with Tee Grizzley.

He was not harmed, but his then-girlfriend, Kaylyn Marie Long, was shot. YoungBoy’s bodyguard was also present and exchanged fire with his attacker. Stray bullets in the exchange traveled substantial distances and struck one five-year-old boy, who lived, as well as 43-year-old Mohammad Jradi, who died. The death of Jradi has not been publicly attributed to NBA alone, nor was his bodyguard charged, given that he was cleared as having acted in self-defense, but being involved in such a fatal occurrence was considered a violation of YoungBoy’s probation. With this, he served a three-month stint behind bars. After finishing his sentence, another judge showed considerable grace and ended his probation over the attempted homicide charges. NBA took this as a cue to do, well, what anyone would probably do after an attempt on their life, and left the state.

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September 2020: Drugs and Weapons     

If anything, it may have seemed that NBA YoungBoy was prospering in the absence of legal trouble as his mixtape 38 Baby 2 and studio album Top, both managed to top the Billboard charts upon their release earlier this year. Still, he finds himself in headlines once more this past week, after being arrested in a possible contraband sweep. NBA caught at least three drug and gun charges, reportedly including “felony possession of drugs and possession of a stolen firearm.” His arrest took place alongside fifteen others after police responded to a call regarding individuals displaying firearms and recording a video. Baton Rouge Police claim the suspects arrested were “Never Broke Again” gang members and “Bottom Boy Guerillas” members as well.

At the scene, officers discovered numerous firearms, including an AK-47, in addition to Hydrocodone, marijuana, digital scales, and Xanax. Furthermore, NBA YoungBoy alone was found to be in possession of $47,000 in cash at the time of the arrest. 

YoungBoy’s lawyer was swift to take up a rigorous defense of his client, stating, “We still have the Second Amendment in the United States. The immediate detention of these black men was illegal in that it violated their Constitutional rights. The subsequent searches conducted by law enforcement were also illegal. Even with the illegal searches that were conducted, no firearms or controlled dangerous substances were found on Mr. Gaulden’s person or in his immediate control. Mr. Gaulden is innocent of the charges he was booked on last night and looks forward to defending himself as such.”