Back in the early 2010s, the Chicago drill scene was flourishing. Names like Chief Keef, Lil Durk, King Von, and G Herbo made their way around the city, turning them into viral sensations overnight. This is the story of a rapper who had clear potential and a diehard fanbase that perhaps could have cemented him into the same tier as the household names mentioned above.

Shaquan Thomas a.k.a “Young Pappy” was from the Uptown side of Chiraq. As a kid, his Grandmother would call him “Pappy,” as a nickname. He sat around the house, reading a dictionary to absorb new rhymes at the early age of four. Several years later, Pappy began to upload tracks to YouTube after he turned 12.

Pappy’s parents ran into issues and split at an early age, causing housing issues for Pappy. Although he was living all over the place, he spent the majority of his time with his father in an area called Rogers Park. Rogers Park is a 15-minute drive North of Uptown. The area is relatively safe; however, these safe living conditions didn’t protect Pappy from violence.

The streets inevitably took a chokehold on him. He started hanging out with the wrong group that had been known for gang-banging. Moreover, Pappy started getting into fights and would get in trouble for bringing weed to school. His record started to build up as a juvenile, and he got even more involved in street life.

Eventually, he claimed PBG and TFG which were Gangster Disciple sets originally named “Insane Cutthroat Gangsters.”

In 2012, tragedy struck. A close friend of Pappy, and a fellow member of PFG, named Anton Sanders a.k.a “Pooh Bear” was shot and killed by a member of a set called “Loccity” reportedly named Munchie during a failed gun trade. A gang called “Pooh Bear Gang (PBG)” was created in his honor.

Pappy took to Twitter to tweet that he would get revenge for Pooh. While behind bars on a gun charge, he started to think about how he could take his music more seriously.

When Pappy got out, he downloaded an application called Audacity on his computer and remixed a few songs including Drake and 2 Chainz's “No Lie.” He didn’t like how the song came out.

Pappy invested money into a studio microphone. He released a few songs but still spent his fair share of time in the streets. His mother allegedly said that he wasn’t really about that life and only did it to create a persona for his music. But the streets told a different story. In 2013, PBG and Loccity were in the middle of a deadly beef.

It’s rumored that Pappy became a large target for Loccity that year after he allegedly shot one of their members named “Lucky.” Pappy took it to the studio and put a bar in his song titled “Competition” about the event. He was one of the only Chicago rappers who was truly living what he was rapping about.

On July 4, 2013, Young Pappy allegedly caught his first body: Blake Lamb. The shooting has gone down as one of the most gruesome murders in the Chicago drill scene. Shots rang out as the victim fell to the floor.

However, the PBG members still wanted to make their mark. They hopped out and shot him eight more times in the face. The craziest part is that Pappy and a few other PBG members swung back to the crime scene after the paramedics arrived and took photos and videos, which they posted, and later deleted, on Facebook.

Residents in the area reported to authorities how unsafe the neighborhood was becoming. Pappy’s friend “2 Cups”’ life was taken by a member of “DayDay World,” a Chicago gang. This led to many mixtapes entitled 2 Cups. Pappy kept sliding on DayDay World for revenge even though Loccity was still targeting him.

They were watching his every move.

In February 2014, Pappy and some other PBG members were on their way to Mcdonald's at around 3 p.m. Loccity members pulled up wearing masks and started firing rounds. Pappy, along with a few bystanders, was hit and survived. However, Pappy’s 17-year-old friend, Markeyo Carr (Keyo), died on the scene.

It was later confirmed… Pappy was the intended target.

A Loccity member named “King Ty” was the alleged killer. King Ty is still around to this day and dissed Montana 300 in a track called “DOA 3” years later in 2017. Scratch that. While writing this article, it has become apparent that on October 27, 2022, King Ty was shot and killed in the middle of PBG’s hood.

After releasing his track “2 Cups” on March 13, 2014, Pappy was sentenced to 60 days on a reckless conduct charge. While he was gone, the song began to gain recognition all over the city. Once Pappy was released, he was able to see the momentum with his own two eyes. He tried to capitalize off the buzz and immediately transitioned to shooting new music videos.

During a shoot near Pappy’s father’s house with his photographer on June 3, 2014, a car spotted Pappy from down the street on Devin Avenue and spun around to chase him down the block, firing shots everywhere. Pappy got away, once again. However, his innocent photographer, Will Lewis, was shot in the crossfire.

One of the shooters was a Traveling Vice Lord (TVL) member named Eric Vaughn. Vaughn allegedly handed his gun to a passenger stating: “Wet that t-shirt up,” when he saw Pappy walking near his dad’s home.

As soon as Pappy got out of the hospital he tweeted: “Wet that shirt.”

Not only were Pappy’s opps focused on his every move, but he now had Chicago PD’s full attention. His music was taking off and he had now survived two murder attempts. Residents of Uptown and Rogers Park were disheartened by the innocent lives lost. The police were eager to get Pappy off the streets but they didn’t have anything to charge him with at the time.

Months later, Munchie (who had killed Pooh Bear) was gunned down. There were rumors that Pappy was involved. Pappy wanted to take advantage of what he thought to be an opportunity by releasing two songs entitled “Faneto Remix” and “After Dark, Pt. 3,” dropping lines about Munchie’s death.

Additionally, he dropped his most popular song to date “Killa,” which has garnered hundreds of millions of views across streaming platforms and was the next step he needed to become a nationwide name.

Police were still on Pappy’s tail. After a physical altercation at the same Mcdonald's Pappy was shot at the year before, he ended up shooting a man in the leg. Although he wasn’t charged with the shooting, he was Chicago PD’s number one suspect. They now had a reason to lock him up.

The police stormed his Mother’s home and searched for hours for his gun, but had no luck. However, Pappy still spent another 28 days behind bars for another “reckless conduct” charge. This gave Pappy another opportunity to rethink his music career.

He finally grasped the thought of fame and fortune. He was so close to taking things to a new level. On May 8, 2015, he released his project 2 Cups Pt. 2, and had the whole hood bumping.

The album was quite possibly one of the best drill albums to date. Songs like “Savages” and “Homicide” are still in my daily rotation to this day. It’s impossible to not hit a max at the gym while listening to these tracks.

In celebration, Pappy planned a mixtape release party and would also celebrate his 20th birthday - which was only a few days away.

During the party, neighbors reported gunshots to authorities. The police took no chances given Pappy’s newfound notoriety.

They sent a swat team of over 50 people to the party and surrounded his house. Over 150 partygoers were arrested and the last to leave was - you guessed it, Pappy himself in handcuffs mocking the police. Pappy bonded out the same day and released his song “Shooters” with PBG member, Lil $hawn.

Rappers started to cosign Pappy, naming him “Chicago’s next superstar.”

Unfortunately, Chicago couldn’t escape gang violence. Not only were the young artists blossoming, but the city was filled with chaos and violence. Heck, there were artists carrying around full-on military-level RPGs and flexing the weapons in pictures on social media.

Only a couple of weeks later on May 29, 2015 Pappy was walking with a friend on the 4800 block of North Kenmore Avenue. It was 1:30 in the morning and it was unclear where he was headed. According to reports, one gunman approached Pappy and shot him in the back twice; paralyzing his body. CPR was performed at the scene and he was rushed to the hospital, where he was pronounced dead at 2:04 a.m.

Undoubtedly, he would’ve been the biggest artist out of Chicago.

“Witnesses reported seeing a shiny black car that may have been associated with this incident” According to Ald. Harry Osterman (48th Ward).

There were many speculations about the murder. No one believed Pappy let his guard up so easily. The predominantly-accepted story was that he was killed by a member of Lil4Mobb (L4M). L4M hung around the area of Wilson and Hazel. They used to go by “HazelMobb” and they were a set of The Four Corner Hustlers (4CH) and TVLs. They had beef with TBG and were cool with Loccity.

In retaliation, PBG struck multiple times. They allegedly killed L4M member, Eric Jordan (EJ) on November, 14th, 2015, and in 2016, almost carried out a hit on a well-known L4M member named Truefoe, killing his friend G-Tuck in the process.

Young Pappy stapled himself as a pioneer of Chicago drill, and his name will be remembered for his raw poetic talent that remains unmatched to this day.