This YSL Affiliate Has Been Arrested. Here’s Why That Could Be a Big Deal

On July 10, Jimmy Winfrey, a.k.a. PeeWee Roscoe, was arrested by Las Vegas police after being a fugitive for over 14 months. Winfrey’s arrest record shows he was charged with battery and using a fake ID to evade justice — but there’s another reason to watch his case closely.

Winfrey was on the run from the YSL trial, which ensnared Young Thug and 27 others, including him, last year. He’s connected to a particularly sensational part of the YSL indictment: the 2015 shooting of Lil Wayne’s tour bus. Eight years ago, Lil Wayne’s bus was shot up on Interstate 285 outside of Atlanta. Young Thug and Birdman were named as uncharged co-conspirators in that case, with prosecutors claiming that Winfrey made multiple calls to them before and after the shooting. At one point during those legal proceedings, Winfrey reportedly implied that Birdman was complicit in the shooting. Winfrey then pled guilty and served time before his conviction was overturned three years later. 

In September 2018, the Cobb County DA’s office told TMZ that they were investigating Thug and Birdman’s potential roles in the shooting. No charges were filed then. With Winfrey now in custody and set to face trial, the 2015 shooting once again comes into focus as a potential worry for Thug, who remains in prison and was recently denied bond for the fifth time. 

Nevada police records mention that Winfrey was also arrested on an outstanding warrant from another state. They don’t indicate what state that is, but it’s safe to assume that he will soon be extradited to Georgia, where he is facing four charges in Fulton County’s YSL indictment: racketeering, violation of the Georgia controlled substances act, participation in a criminal street gang and a gun charge. In January, he was severed from the 14-man YSL trial along with Justin “Duwap” Cobb because they hadn’t yet been arrested. 

In 2018, Winfrey pled guilty to six of 27 charges related to the 2015 shooting of Lil Wayne’s tour bus, and was sentenced to 10 years in prison and 10 years of probation. He later had the conviction overturned after a successful appeal. The Atlanta Journal-Constitution reported that the Georgia Supreme Court agreed with his assertion that then-Cobb County Superior Court Judge Mary Staley Clark had interfered with his plea negotiations and threatened him with a lengthy sentence if he went to trial. In 2020, Winfrey took an Alford Plea on two of the 27 charges from the shooting — still maintaining his innocence — and he was released on time served. (He was then sent to Florida to face unrelated 2014 drug charges.)

Observers of the YSL case have made much of the April 2015 tour bus shooting, whose alleged details are laid out in Winfrey’s indictment from that year. On the night the bus was shot in Georgia, Thug was performing in Wayne’s hometown of New Orleans. Winfrey’s 2015 indictment claims Thug “was shouted off the stage in New Orleans with the crowd chanting for Lil Wayne.” The two had been embroiled in controversy related to Thug’s plans to call his next album Carter 6, a reference to Wayne’s seminal album series (he later changed the title to Barter 6). Birdman had been a longtime mentor and label boss to Wayne, but earlier that year, Wayne had sued Birdman’s Cash Money Records for $51 million and began dissing Birdman on record (the two have since been seen together). At the time, Thug was Birdman’s new protege as one-third of Rich Gang, and perhaps he saw fit to needle Wayne with the album title out of loyalty.  

But Winfrey’s 2015 indictment appears to suggest that the disagreement may have gone far beyond album-title antics. Wayne was performing in Thug’s hometown of Atlanta on the same night as Thug’s New Orleans performance. The indictment alleges that “at the time Dwayne Carter [a.k.a. Lil Wayne] began his performance, Blood gang members associated with Jeffrey Williams [a.k.a. Young Thug], to include Jimmy Winfrey, left an Atlanta location known as the Vault in vehicles and traveled” to Compound, the venue where Wayne was performing.

Winfrey, who was Young Thug’s tour manager at the time, allegedly got into an argument with Wayne and was removed from Compound. Police claimed to have then observed Winfrey in a white Camaro with an assault rifle, and said that he fled when they tried to apprehend them. Atlanta police escorted Wayne’s tour buses out of the city for protection, but Winfrey allegedly followed them onto Interstate 285 and shot into them once the escort left. No one was hurt, but the buses sustained $20,000 in damages.

Cell phone records indicated that Winfrey called Thug eight times in 12 minutes during the time that the police were escorting Wayne’s tour buses and that he called a phone registered to Bryan Williams, a.k.a. Birdman, after returning to Atlanta. In July 2015, Birdman denied being involved in the shooting, said he didn’t believe Winfrey was involved, and claimed that the phone call wasn’t from Winfrey, but from someone in Wayne’s camp to tell him about the argument between Winfrey and Wayne (both phones were registered to Cash Money).  A month later, court papers revealed that Winfrey alleged “[Birdman’s] financial dispute with [Lil Wayne] is what ultimately led to the shooting” and that “[Birdman] should be held liable as a party to the crime.”

In 2018, Alvin Lewis, one of the tour bus drivers, filed a lawsuit against Birdman and Young Thug. He alleged that Winfrey was offered $250,000 and a Porsche from Birdman for the shooting. Court records from the civil case leaked online, including a jail call in which Birdman told Winfrey, “It’s time for you to come out here and get your money, man…You done did everything you could do… It’s an eye-opener, bruh. Strictly business, man.” Birdman denied that his comments had anything to do with the tour bus shooting, telling TMZ he “would never associate with someone who tried to harm Wayne.”

Winfrey has a lengthy history in the music industry. There’s online footage of him hanging with Lil Baby in January 2022, Fabolous at some point in the 2000s, and a 2007 studio session with Lil Wayne and T.I. In 2009, he appeared on T.I.’s Road To Redemption reality show, portraying a disadvantaged youth that T.I. was mentoring. Producer Wheezy told The Fader that Winfrey “been in the big leagues in the game” and helped him get a footing in the industry by introducing him to Young Thug. Winfrey was also a member of Bankroll Mafia, a T.I. and Thug-led supergroup which T.I. called “a collective that includes a lot of personal and professional constituents throughout the industry, in and out of our elements.”

Winfrey was granted bond for the fak- identity charge but is being held without bond on the other two charges. His first Las Vegas court date is set for Aug. 1.