“I didn't even mean to shoot him, he just caught me by surprise/I reloaded my pistol, cocked it back, and shot him twice/His body dropped down to the floor and he got teardrops in his eyes/He grabbed me by my hands and said he was afraid to die/I told him it's too late, my friend, it's time to say goodbye/And he died inside my arms, blood all on my shirt.”

The lines read like a crude confession to a callous murder. They are actually lyrics to the second verse of embattled rapper YNW Melly’s 2017 breakout hit “Murder on My Mind.” Considering the rapper is currently being charged with the homicides of two of his associates on Oct. 26, 2018, the bars now have a surreally prophetic feel.

Melly’s current legal situation is the stuff shows like The First 48 and podcasts such as Disgraceland are made of. But it is far from his first rodeo with the law. Born Jamell Demons, in the sparsely-populated bayside town of Gifford, Fla., the 19-year-old artist’s ascension in the rap game through menacing melody raps was essentially launched during a jail bid for a shooting when he was still a minor.

In the past two years, Melly has been on the wrong side of the law a few times as he has built his résumé with the projects Collect Call (2017) and I Am You (2018), and tracks such as “Slang That Iron,” “Virtual (Blue Balenciagas)” and “4 Real.” He was even able to corral a Kanye West feature "Mixed Personalities" on his January project We All Shine, which debuted at No. 27 on the Billboard 200 chart.

That is all in limbo with Melly, currently imprisoned in Broward County Jail, being charged with first-degree murder in the shooting deaths of two associates, YNW Sakchaser and YNW Juvy, who he mourned following their passings. Melly is also implicated in another murder.

With the ascendant rapper possibly facing life in prison in one of the most intriguing rapper-related murder cases in recent memory, XXL compiles a timeline of the YNW Melly’s legal troubles dating back to before the fame.

  • YNW Melly Arrested for High School Shooting

    Oct. 20, 2015

    YNW Melly, then 16, is arrested after shooting into a crowd outside Vero Beach High School in Vero Beach, Fla. No one is hit in the shooting. The teen is slapped with four charges, including three counts of assault with a deadly weapon in addition to one count of discharging a firearm in public. Still a minor, Melly ends up spending a year in jail for the crime and gets his GED while behind bars. It is during his time on lockdown that he pens his breakout single "Murder on My Mind." Melly is released in March 2017.

    YNW Melly via YouTube
  • YNW Melly Arrested on Gun and Drug Charges

    June 30, 2018
  • YNW Melly Arrested on Drug Charges

    Jan. 3, 2019

    Melly is again arrested in Lee County, Fla. and charged with possession of marijuana not more than 20 grams and possession and/or use of drug paraphernalia. He spends three weeks in jail before being released on Jan. 25. During his jail stay he releases We All Shine featuring Kanye West on "Mixed Personalities."

    YNW Melly Via Twitter
  • YNW Melly Arrested for First-Degree Murder of YNW Members

    Feb. 13, 2019

    News breaks that Melly has been arrested by police in Miramar, Fla. for the double homicide of fellow group members YNW Juvy (Chris Thomas, 20) and YNW Sakchaser (Anthony Williams, 21). Both men were killed on Oct. 21, 2018 in what was first believed to be a drive-by shooting and were even driven to the hospital by YNW Bortlen. Police now believe Melly is responsible for the killings and Bortlen helped assist in covering up the crime.

    "Jamell Demons, a.k.a. YNW Melly & Cortlen Henry have been arrested and charged with two counts of first-degree murder," begins a statement Miramar PD. "The victims, Anthony Williams & Christopher Thomas Jr., were killed on 10/26/2018. The investigation, supported by forensic evidence, has concluded that Demons shot and killed Williams & Thomas Jr. and that Demons and Henry staged the crime scene to resemble a drive-by shooting."

    Melly maintains his innocence. On Instagram, he posts a photo of the quartet along with the caption, "To all my fans and supporters no I did not get locked up in Washington , but I am turning myself in today I want you guys to know I love you and appreciate every single one of y’all, a couple months ago I lost my two brothers by violence and now the system want to find justice," Melly wrote. "[Unfortunately] a lot of rumors and lies are being said but no worries god is with me and my brother @ynw.bortlen and we want y’all to remember it’s a ynw Family I love you @ynwsakchaser1 and @ynwjuvy #freeus."

    Bortlen is apprehended in Houston and extradited back to Florida to face charges of murder and accessory to murder. Melly has a bail hearing and is ultimately denied bond.

    Broward County Sherriffs office
  • Melly and Bortlen Named as Suspects in 2017 Murder

    Feb. 21, 2019

    Melly and Bortlen are named as possibly being linked to the 2017 shooting death of Deputy Gary Chambliss of the Indian River County Sheriff’s Department, which occurred in Gifford, Fla.

    According to a source, on the day of the shooting, Melly and Bortlen were standing with a group of men who chucked a bottle at a passing car. An occupant in the vehicle fired a weapon at the group and one of the rappers allegedly returned fire. Chambliss, who was standing 170 yards away, was hit with a stray bullet and died.

    Captain Tony Consalo, head of the Sheriff’s Office’s criminal investigations division, tells the VeroNews, “After that shooting in Miramar, our detectives will be following up for possible information in connection to the Garry Chambliss homicide. Perhaps, given their current situation, they might be able to shed some light on the case.”

    YNW Melly / YNW Bortlen via YouTube
  • More Details Emerge in Juvy and Sakchaser Murder Case

    Feb. 25, 2019

    More details emerge regarding the deaths of YNW Juvy and YNW Sakchaser. According to police documents released to the public, authorities claim to have forensic evidence that points to YNW Melly being the triggerman after concluding both were shot from inside the vehicle they died in, not from the outside, as would have been the case if the drive-by story were to be believed.

    Police’s timeline of events contend Melly shot Juvy and Sakchaser and rode around with their dead bodies while he came up with a story to tell police. Bortlen then drove the dead men to the hospital and offered up the drive-by story. The evidence that backs up their claims includes shell casings found inside the vehicle and Snapchat messages where Melly appears to address the incident.

    YNW Juvy / YoungNiggaWorld Sakchaser via YouTube (2)
  • Melly Pleads Not Guilty in Double Murder Case

    March 5, 2019

    YNW Melly pleads not guilty to two counts of first-degree murder.

    YNW Melly via YouTube
  • YNW Melly Faces Death Penalty

    April 16, 2019

    On April 16, 2019, the State Attorney's Office in Florida files court documents announcing its intent to seek the death penalty in the case. The State believes it can prove Melly killed his friends for financial gain. The court documents go on to say “the murder was especially heinous, atrocious or cruel, and he committed homicide in a cold, calculated and premeditated manner."

    Broward County Clerk's Office