Pooh Shiesty faces life in prison: What we know about Memphis rapper's upcoming trial

Memphis rapper Pooh Shiesty started the year as one of hip-hop’s hottest new artists, but after a series of arrests he’s now facing the possibility of life in prison. 

Shiesty — real name Lontrell Williams — has been jailed in Florida since July on charges related to an October 2020 incident where he was allegedly involved in the robbery and shooting of two men outside a hotel in Miami-Dade County.

He has pleaded not guilty to the charges in a federal indictment, which carry a possible maximum sentence of life in prison. His trial is set to begin Oct. 25.

The Commercial Appeal reached out to Shiesty's attorneys and record label for comment, but did not receive a response.  

Here are five things to know about Shiesty’s career and his legal troubles.   

Rising rapper: 'Shiesty Season' is here

Chosen by Spotify's "Rap Caviar" as one of the "10 Artists to Watch in 2021," the 21-year-old Pooh Shiesty became the latest young Memphis rap sensation, hitting the Billboard Hot 100 and Emerging Artist charts and making Rolling Stone's "Breakthrough 25" rankings. He was handpicked by rapper-mogul Gucci Mane to sign to his The New 1017 label and released his "Shiesty Season" mixtape earlier this year. 

Raised around South Memphis' Cane Creek Apartments, Shiesty is a second-generation Memphis rapper. His father founded the Bluff City label Mob Ties Records and rapped under the name Mob Boss, steeping him in the family business from a young age.

Shiesty got his start with a group of friends known as Choppa Gang. After a couple years away from Memphis, living with his mother in Texas, Shiesty returned to the Mid-South and started focusing on his music. As part of the Choppa Gang collective — which also included Big30, Choppa T and K Shiesty — he first gained notice with the track "Breaking News," released in 2018.

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On the heels of "Breaking News," Shiesty began to develop a major underground buzz with performances on tracks like "Hell Night" (featuring Big30), "Day One" and "Choppa Talk." Further fame followed in 2019 with "Shiesty Summer" released that August. The track would go viral, with the YouTube video for the song eventually getting close to 10 million views. His numbers would grow exponentially with the anthemic follow-up "7.62 God," which would further put Shiesty on the music biz map.

In spring 2020, fate would intervene in the form of Grammy-nominated, platinum-certified rapper Gucci Mane. Gucci messaged Shiesty on Instagram, and in short order offered him a record deal, specifically a chance to be part of his The New 1017 label venture with Atlantic Records. 

The association with Gucci quickly helped up Shiesty's profile, as did a series of further hits and notable collaborations including "Monday to Sunday" (featuring Lil Baby and Big30), a remix of "Main Slime" (with fellow Memphians Moneybagg Yo and Tay Keith), and his "Back In Blood" (a team-up with Lil Durk that would eventually go platinum). 

Shiesty hit the upper reaches of Billboard this spring, placing at No. 4 on the albums chart with "Shiesty Season," while his video for the single "Back in Blood," hit the No. 1 spot on YouTube's U.S. video charts, and he made his national TV debut on “The Tonight Show Starring Jimmy Fallon.” 

Personal loss: Pooh Shiesty's brother dies

This past February, just as he was celebrating his growing success, Shiesty lost his brother, fellow hip-hop artist TeeDa P. Born Tarrance Henderson, TeeDa P died on Feb. 28. 

While the family did not confirm the cause of death, various outlets reported he had been battling brain cancer and Pooh Shiesty had canceled a series of concerts just before his passing. TeeDa P had been gaining notice himself as a rapper since releasing a series of singles in 2019. His new album, "Halftime," came out earlier this year. 

Shiesty publicly mourned his brother and received messages of support from a number of fellow rappers, including Memphis-rooted superstar Drake. 

Legal troubles: Pooh Shiesty arrested in Florida

Shiesty's legal issues began in October 2020, when federal authorities allege he was involved in the robbery and shooting of two men outside a hotel in Miami-Dade County, Florida.

The FBI would eventually indict him and two others on charges of discharging a firearm during a violent crime, conspiracy and robbery under a law regulating commerce. Shiesty, along with Jayden Darosa and Bobby Brown, went to the Landon Hotel in Bay Harbor Islands, Florida, in October to purchase "high-end athletic sneakers" and marijuana, according to the criminal complaint by Miami-Dade FBI Detective Elio Garcia. 

Shiesty arrived in a McLaren he rented from one of the victims and wanted to negotiate the car's rental as well, but during the transaction, he and Brown shot the men — one in the hip and the other in the butt, according to the court documents. The FBI said surveillance footage captured the shooting and after law enforcement spoke with the victims they identified one of the suspects as Shiesty.

While leaving the scene, a Louis Vuitton bag — which had $40,912 in cash — fell out of the McLaren and, according to the complaint, Shiesty had posted guns and $100 bills on Instagram days before the robbery.

Law enforcement utilized the rapper's social media account and found the same bills in the Louis Vuitton bag were also in his posts, the court document said.

Shiesty was arrested but released from custody shortly after the incident. 

Strip club shooting: Pooh Shiesty arrested in Florida again

Shiesty was again arrested in June 2021 in connection with a Memorial Day weekend shooting of a security guard at strip club in Northwest Miami called King of Diamonds. 

According to a review of the affidavits in the case by Rolling Stone, the incident began when Shiesty “allegedly pulled a black semi-automatic pistol from his waistband and waved it around the King of Diamonds club in Miami… after he dropped some cash on the ground and purportedly worried patrons might grab it. As security tried to remove him from the building, he allegedly fired a shot, striking a security guard in the ankle.”

According to his attorneys, Shiesty is facing a “mandatory minimum of 20 years” if convicted of the shooting. 

On June 9, Shiesty was granted a $10,000 bond by a Florida judge on aggravated battery charges related to the King of Diamonds incident. But he was ordered to remain in jail until another judge ruled on his status in the Landon Hotel shooting. 

A few weeks later, on June 29, Shiesty was formally indicted in the Landon Hotel shooting. In early July, a federal judge ordered that he be held without bond. Shiesty has been held at the Turner Guilford Knight Correctional Center in Miami since then. 

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Court case: Pooh Shiesty trial set for Oct. 25

According to a recent report in Rolling Stone, Shiesty and his attorneys had petitioned the court to delay his trial to Dec. 6, in order to “properly build his defense against claims he was part of an armed drug-trafficking conspiracy dating back to 2019.”

The outlet notes that, “Prosecutors said they were fine with a delay but that conflicts would push the trial out to February. The feds also told the court they were reviewing ‘new allegations’ and a ‘potential superseding indictment.’”

But earlier this month, Shiesty and his lawyers did an about face in the strategy, and instead decided it was “in their best interest to proceed to trial” at the end of October. The first day of trial is set for Oct. 25 in the Southern District of Florida Court in Miami. 

In the meantime, Shiesty’s friends and fellow rappers, including his longtime Memphis partner Big30, have rallied around him. Big30 recently released a track called “Free Shiest Life” and has posted support for his friend on social media with the hashtag, #FreeShiesty. 

Commercial Appeal reporter Dima Amro contributed to this report.