Jay 305 was supposed to be a central figure of the new West Coast movement. A naturally charismatic and friendly guy, the 30-year-old South Central-born rapper seemingly has his own six degrees of separation with everyone in Los Angeles—a trait that makes him sort of an ambassador to the city, a neutral player in an area known for affiliation. Though the man born Jay Cummins​ has only been rapping for three years, he has already made a huge splash with his groupie-shaming regional hit “Youzza Flip.” His momentum slowed down a year ago after turning himself in for a gun charge at the height of “Flip”’s popularity (Wiz Khalifa and Juicy J hopped on a remix of the song a month after he went in), a charge he chalks up to his bad temper: “I had a gun, I did something with [the gun], and I was caught by a bitch snitchin’. Fuck that bitch.”

Since his release from prison in February, 2014, has been working toward rebuilding the momentum that was cut short after “Youzza Flip” was released. His upcoming album, Takin All Bets, is a project that he hopes will get him back into the the conversation musically. He’s a popular figure in the streets, and he’s also connected to some of the most popular and noteworthy artists in the city like DJ Mustard and Kendrick Lamar, but he has never had the opportunity to properly show off just what he can do as an artist. Fortunately, Jay’s short career has been given a second chance, and he is making every effort to make the best of it this time around.

I meet Jay one morning during his daily workout at Dorsey High School’s football field, accompanied by his friends G Man and Joshua. Decked in all black and nearly all L.A.-based brands (from Phreshcru shorts to a beanie from Casey Veggies’ own Peas N Carrots line) besides his Nike Tech Fleece pants and Huarache sneakers, he looks more ready to work out than his two friends. This stringent dedication to routine is perhaps an after effect of Jay’s recent jail stint, a moment that he says drove him to take his craft more seriously. “I’m usually out here earlier, at like 6 a.m.,” he says as he jogs around the elderly people who share the track with us.

“Y’all playin, you ain’t trying to run. I got three more laps,” Jay says as we all take off in a sprint. I take one lap around next to the heavily tattooed G Man before we realize that we’re completely out of shape and stop for a rest. “I known 305 since I was 8,” G Man says, preparing his phone to Snapchat a picture with the rapper when he comes around the track. G Man explains that he got kicked out of Dorsey High after a few weeks for “fighting and shit,” and that he is one of the many young people who Jay’s rise to notoriety has effected in a positive manner. Grabbing his shirt adorned with “Dressed to Kill,” G Man says that Jay was the one who bought the printer to create the shirts.

Jay, like G Man, had a troubled upbringing. He relocated to Miami from Los Angeles when he was 11 years old because members of the Crips were trying to kill him. “I was doing young nigga shit. It caught up to me,” Jay says about the incident without giving away too much. His four-year stay in Miami’s Carol City district taught him that there were very few differences in gang politics between the two coasts, a situation his friends know all too well. “I can’t stop [G Man] from doing everything. Over here is like the devil. I try to keep him out, but at the end of the day he has shit he has to learn.”

Dorsey High is a massive school that is located in an area of Los Angeles called Baldwin Village. Better known as the Jungles, the area is either named for its picture-perfect landscaping or the fact that it is home to major gang activity. With a decades-long rivalry that goes beyond football drama (Dorsey is known for its blood affiliation, and Crenshaw for Crips), the immediate danger that surrounds those trying to make it out of the inner city is an underlying pressure to succumb to gang banging. “A lot of people don’t realize what they gang banging for,” Jay says between pull-up reps. “You were told [to] hate this nigga because they are from this hood, and then another nigga is telling someone else the same thing. It’s a cycle.”

Hopping in his black Dodge Challenger, we cruise around the Jungles, the first stop on our tour of the other side of L.A. Most of the people here are being moved to east L.A. as gentrification grasps what is left of the housing in the area. We drive past landmarks such as the cul de sac from Training Day where Denzel Washington’s character Alonzo had a stand off with the residents. That scene portrayed a neighborhood united against a corrupt establishment, but today it is empty save for some trash and broken furniture.

The four of us stop to take note of the closing of the popular restaurant/bar Jerry’s Flying Fox. Staring at a sign that says “We Are Still Here” posted next to the “Closed” marquee, Joshua recalls different stories and familiar faces associated with the bar. “This was Supper Club, before Supper Club!” he exclaims as he takes pictures. He’s no stranger to the music industry, and as a rapper/singer he claims to have had a few deals before meeting Jay in 2003. “I played him Soulja Boy’s ‘Gucci Bandanna’ beat, and he did a freestyle over it,” Joshua says, adding that even though Jay was rough around the edges he showed promise.

Jay mentions that his standout feature on “Ghetto Tales” from DJ Mustard’s 10 Summers album was crafted in a similar way. “The verse is all true. I freestyled it. The raid by my house, the gun in the rental car. All of it.” It’s abundantly clear that Jay demands to have everything connected with him to be authentic, from his music to his name. It’s why his upcoming project, Takin All Bets, stresses how natural making music comes to him. “I never begged for anything when it comes to music,” he says. “Like, with [“Ghetto Tales”] me and Mustard were in a parking lot, and I played him records. He chose ‘Ghetto Tales.’” 

After breakfast at Village Inn, Jay pays the tab for everyone with his last $40 in cash, we part ways with G Man and Joshua, and Jay takes me on a trip through the hoods of Los Angeles. Our next stop is Nipsey Hussle’s family-owned Slauson Tees store. “We can’t stay here long—it’s enemy territory,” he says as we get out of his car that’s still running. Even though he doesn’t gang bang, his affiliation with the Jungles is dangerous in the primarily Crip neighborhood of Slauson. We stay for a short time, saying hello to Nipsey’s brother and father while Jay stands around and talks about music and working out.

I never begged for anything when it comes to music.

We soon find ourselves deep in the heart of South Central, making stops at the Slauson Swap Meet, Nickerson Gardens, and even YG’s old stomping grounds in Compton. You turn down the wrong street, or say the wrong name and you’re in deep shit, but Jay can easily name off which gang and which set resides on which block. He expresses a level of care when driving through, not out of fear but because it seems like everyone there is hardwired to follow these rules. “I wish it was all peaceful,” he says as we drive through Compton. “It’s never gonna be. As much as people try to protest, it won’t be.”

As we pull up through the busy area of Leimert Park I bring up Dom Kennedy, and Jay’s face lights up at the mention of the popular independent rapper who also grew up in the area, and for good reason. Jay signed to Dom’s Other People’s Money label, and is one of the collective’s first artists. “Within the last 12 years we been tight,” Jay says. “Watching him showed me the game.” Dom’s moves are calculated—he rarely releases new material outside of guest verses or whole projects—yet his strict DIY methods have captured him a worldwide audience in spite of the big business model of major labels, a move that Jay 305 eschewed by signing with Interscope a few months ago. When I ask Jay if Dom would be following him to the legendary label, he says that he would probably stay independent forever, but Dom did support Jay’s choice to sign with a major.

Image via Jonathan Weiner 

It’s during our ride through Leimert Park when he finally opens up about the passing of his close friend Tiny M, who was one of three people who died in a fatal car crash a year ago in this very neighborhood. His death sent ripples throughout Los Angeles. YG even mentioned his name on his critically acclaimed debut album, My Krazy Life. “We used to people dying and getting shot,” Jay says as he points to the exact area where the crash happened. The fact that Tiny M’s death came from a car crash and not gang violence was a startling reversal of the environmental norm. “A month after I turned myself in, Tiny M passed,” he says. “That shit made me stronger. All of these bad situations. It built up a shield for me.” The string of unfortunate events turned into a moment of awakening for Jay when he got word that Kendrick Lamar shouted him out on T.I.’s “Memories Back Then.” “Watching him perform was a reality check, like…what the fuck am I doing in jail?”

I ask Jay 305 if there is any pressure to conform to the new movement in the West Coast, and before answering he reflects for a few seconds. “I’m going to do me regardless,” he says. “We all deliver the same message, but differently. I may want the Ferrari, but I’m feeling like a lowrider. I want the foundation of my music to reflect that. Built from the ground up. That’s me.” Jay's unflinching resolve to stay true to his city s something he shares with many of the new artists coming from L.A. Now it’s his turn to continue to strengthen the foundation.

Justin Davis is a writer living in L.A. Follow him @OGJOHNNY5.