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The first time George Prajin took Peso Pluma shopping for a music video, they didn’t see eye to eye. “I wanted him to go John Varvatos rock’n’roll, and he wanted to go to Burberry,” Prajin recalls. Considering that the video would also feature regional Mexican artist Luis R Conriquez for their 2022 collaboration, “Siempre Pendientes,” “I was like, ‘I don’t know about that,’ ” he adds. But, as Prajin proudly admits of the all-plaid ensemble (complete with bucket hat) that Peso insisted upon (and which perfectly contrasted with the gritty desert setting), “He was right — and after that I learned not to go against him.”

That implicit trust now goes both ways — and Prajin, 52, has earned it. As the son of Antonino Z. Prajin — who owned Prajin One Stop, a music retailer and distributor that sold to over 3,000 stores across the United States and Mexico and had more than 20 warehouses throughout Southern California in its 1980s and ’90s heyday — the music business has always been in his blood. “Some people do what they love. Some people are born into a trade. I got the best of both worlds,” he says, speaking in a green room at the Honda Center in Anaheim, Calif., hours before a recent Peso Pluma show there.

After graduating from University of California, Los Angeles in the mid-’90s, Prajin founded the independent label Z Records, which scored early success with Jessie Morales (known as El Original de la Sierra), an Angeleno who loved West Coast rap and Mexican music and who ruled Billboard’s Top Latin Albums chart with his Homenaje a Chalino Sánchez in 2001. But when physical record sales plummeted, Prajin One Stop shuttered in the late 2000s — and so did Z Records. “It was hard to make money with music during that period of time,” he recalls. “And so, I got disillusioned. I got a little depressed — but I tried to stay very close to music.”

Prajin went on to earn a degree from Southwestern University School of Law, becoming a sports and entertainment attorney and establishing his own practice while producing music on the side — and retaining ownership of the Z Records catalog. But in 2008, thanks to his love of MMA (and friendship with fighter Tito Ortiz), he entered an entirely new world: the Ultimate Fighting Championship. Prajin spent the next decade-plus focused on representing UFC’s top talent as an agent and a manager, earning a reputation as a master negotiator. “It’s educating yourself on the deal and being two steps ahead — and knowing what you’re asking for is valid,” he says.

By 2019, Prajin — who had continued to do music business work even as he dove into the UFC world — and his practice were negotiating “massive deals” for record labels. At the same time, he noticed a catalog-driven uptick in Z Records’ revenue and, on the advice of his law partner, Anthony Lopez, reentered the industry, launching Prajin Parlay in 2021. “I was looking for something that had nothing to do with any of the clients I was representing, and I started going back into the ’90s,” he says. And so, with the new Prajin Parlay, he soon helped launch Época Pesada (a group of corrido giants who were then in their 40s) and revive the career of Lupillo Rivera.

Soon, Prajin was again focusing on music full time, and his first major signing (in partnership with Grand Records) was Mexican singer-songwriter (and future star) Junior H. But it was an early management signee who would define his storied career — and help him emerge as one of Latin music’s most powerful and admired executives.

When Prajin first met Peso Pluma (born Hassan Emilio Kabande Laija) in 2019, thanks to an introduction from his former client Morales, the then-unknown artist was walking around Prajin Parlay Studioz in Anaheim playing guitar. “I was really intrigued by him,” Prajin recalls with a far-off look in his eyes. Morales was trying to help the young artist find management to no avail; given that Prajin himself had just reentered the industry, he, too, initially passed.

Morales’ father, Herminio Morales, signed the future superstar, but soon became too ill to work. And so, by 2022, the offer was back on the table — and this time, Prajin said yes. (Herminio, who is healthy today, remains involved in Peso’s career.) “I [waited until I] felt like I could really put up my sleeves and do what I do best,” Prajin explains.

Apparently, that was developing a global groundbreaker who has repeatedly made Billboard chart history while helping to elevate música mexicana from “the genre that has always taken a back seat,” as Prajin puts it, to the forefront of the mainstream.

“I’m not going to take all the credit because [label] Rancho Humilde, Natanael Cano, Junior H and all these other artists brought something that first, second and third generations of Mexicans born in the United States were lacking,” Prajin says. “But Hassan took that road and connected it to the international highway.”

Prajin now admits that when he first met Peso he was a bit confused. “I couldn’t tell what type of artist he was,” he says. “I thought he was a rapper, or was he a rocker? [The last] thing I thought of was a corridos singer. When we first started talking, he told me he wanted to do reggaetón. He wanted to do everything.” (Prajin even had him record a Pink Floyd song “to see if he trusted me.”)

“I said, ‘I love that, that’s what I want, but I’ve been doing this for 20 years, and it’s tough,’ ” Prajin continues, noting how in the past he’d only had fleeting success with rappers recording over banda beats. But, critically, Peso didn’t want to blend anything; he wanted to own every clearly marked lane he explored.

Together, they made a plan “to focus on his core audience, regional Mexican, and really build that. And at the same time, reach out and get a feel of these other genres and take it from there.” And they’ve done just that. In 2022, Peso made his Hot Latin Songs debut with “El Belicón,” with Raúl Vega. The following year, he scored the most entries on the chart of any regional Mexican act — and his team-up with Eslabon Armado, “Ella Baila Sola,” became the first regional Mexican song to enter the top five on the Billboard Hot 100 (where Peso has now charted 31 songs).

Peso’s third album, 2023’s Génesis, scored the highest placement on the Billboard 200 for a música mexicana album ever, debuting at No. 3. This year’s Éxodo double album also debuted in the top five, and for its second half, Peso enlisted several nonregional heavy hitters including Cardi B, Quavo, Anitta and DJ Snake. In August, Peso scored one of his biggest features yet, replacing Bad Bunny on Ye and Ty Dolla $ign’s “Drunk,” off the new deluxe version of Vultures 2. (“He couldn’t believe it,” Prajin says, “because they’re so mysterious. They don’t even tell us until the song is released.”) Lately, Peso has been walking onstage to Black Sabbath; Prajin thinks he could do a rock album one day.

Their relationship has now expanded beyond just music to include Double P, Peso’s imprint through Prajin Parlay Records that launched in April 2023. (Prajin is the imprint’s co-founder and COO.) By December, Double P had signed a distribution deal with The Orchard, and in August, the label’s publishing division signed a global administration deal with Downtown.

Today, Double P’s roster boasts a tight-knit crew that shares talent — and Peso’s friendship. As CEO and head of A&R, Peso has strategically signed Mexican music acts Vega, Jasiel Nuñez, Tito Double P (Peso’s cousin and one of his co-writers) and Los Dareyes de la Sierra, among others.

“We’re building a team and going together, and that’s what I love about Hassan,” Prajin says. “Jasiel Nuñez was a friend. They made a deal — whoever makes it first is going to pull the other guy with him, and [Hassan] did that. He pulled him with him on tour. We’ve signed him. That’s their philosophy. We’re a real community.”

Plus, as Prajin says, having Peso as a partner helps him stay on top of his management game, too. “Because you really want to give the attention to Hassan, but then you don’t want to sign other artists and not give them the attention that they deserve… He’s always like, ‘Hey, make sure that everybody’s getting the attention that they need, too.’ ”

And as Prajin Parlay has proved over time, one rising tide can indeed lift all boats. In 2023, it finished atop the year-end Hot Latin Songs Publishers chart — Prajin proudly displays the trophy at his house next to his Grammy (honoring Génesis as best música mexicana album [including Tejano] at the 2024 awards). “One of the reasons why we won that publisher of the year award is [because of] Tito Double P,” Prajin says, crediting his songwriting savvy. “[He] then developed as an artist, and today, we released his first album.

“We’re providing those label services, and we’re doing it inclusive of the same management fee that any other manager would charge,” he continues. “A lot of people tell me that’s a crazy notion, but we’re not going to get rich or poor overnight.”

That same thought process led Prajin to restructure Peso’s five-year record and management deal just nine months in. Prajin had seen his early client Jessie Morales make a healthy living off music, only to end up “on hard luck,” and he never forgot it. “I always told myself, especially when I was practicing law, that if I had the chance to do this again, I would teach [artists] to not only be wary of how they spend their money, but to also build their own team. Have their own lawyer, have their own CPA. I want them to make sure that going forward, whatever they do in their lives, they’re going to make the right financial decisions. I fought hard for [Peso] to have his own [attorney in] Mexico. He has his own CPA. And then he has a person that audits the CPA.

“When I saw him making the kind of money that he was making… The artists should be the ones seeing the benefits, and that’s why we changed our deal,” Prajin continues. “I restructured it and made him a partner in Double P. It’s the right thing to do — and just one of the few times in life that something good turns into something great, because we’re killing it.”

Prajin, who is warm and attentive, says his father’s own “big heart” inspires him as an executive. “His kindness, his generosity, those are the things that have [helped me excel],” he says. “You could be a shark. But I don’t think those guys last too long. It’s all about networks. Right? I think a lot of the things that we accomplished were because I was able to pick up the phone and reach out to anyone. Everything comes full circle.”

And Prajin Parlay’s betting-inspired name tells its own full-circle story: Prajin has often said when something works, he doubles down. In the years to come, he says he’s “doubling down on everything” — beginning with Double P Records, saying the label is in the middle of completing a business transaction that will allow it to “really double down.”

“Double P Records and Prajin Parlay in five years are going to be a global brand,” he says, noting that in the next year or so he hopes to open offices and a recording studio in Madrid. He also has plans to grow the management roster and maybe even acquire other catalogs or companies. He’s also considering a sports division: “We’ve talked about it, yes,” Prajin says, adding that he and Peso are both fans of combat sports, and even share a boxing coach.

He admits that as a manager, what takes up most of his time each day is “trying to make everyone happy… I’m constantly trying to make sure everybody takes vacations, has their personal lives. You know, I’ve lived my life, I haven’t had any kids. I’ve devoted myself to my artists and to my athletes. And am I going to regret it down the road? I might. So I always tell people, ‘Think about yourself, too. This job isn’t your only focus.’ ”

Fortunately, Peso has been planning ahead for quite some time. The artist has long admired Jay-Z, and Prajin believes Peso is already following in the rapper’s footsteps to becoming a mogul himself. As for Prajin, he says his five-year plan looks a lot like an exit route, before laughing through a nervous smile: “No, I’m just kidding.”

He mentions how the other day, he and Peso were reminiscing when the artist told him, “You changed my life.”

“He changed my life as well,” Prajin says. “He’s allowed me to love music again, and also reach a lot of the goals I made for myself that I thought had passed.”

This story appears in the Sept. 28, 2024, issue of Billboard.