In 2015, an entourage of close to 30 men drew guns among one another during a traditional Christmas parranda in Puerto Rico. The scene turned into something straight out of a movie when a pair of gangsters clandestinely attempted to kidnap local rapper Anuel AA. After a brief scuffle and flagrant shouting match, however, the man born Emmanuel Gazmey Santiago went on to finish the evening’s holiday spree in the boisterous company of his loyal posse.

Months later, after ushering in the new year on a promising note by featuring on one of Latin trap’s first global hits – De La Ghetto’s sex anthem “La Ocasion” with Arcangel and Ozuna – someone delivered Anuel AA a divine premonition of sorts: “If you keep talking about this stuff in your songs, something really ugly is going to happen to you.”

A Puerto Rican music legend, Hector “El Father” of reggaeton-turned-son of God, paid Anuel a visit to share his foreboding message. “He and I did not know each other,” explained Anuel, who prides himself on waxing poetics about the real-life experiences Hector was concerned with, “but God spoke to him and Hector felt he needed to reach out to me. When he warned me, he said it with so much conviction that he even cried.”

Having forged a legacy of his own as one of the key trailblazing reggaeton entertainers of the ‘90s who later signed a deal with JAY-Z’s Roc-A-Fella Records, Hector – now a devoted Christian – understood life imitated art when it came to Anuel’s lyrics.

“My lyrics talked a lot about God and the devil, so when he told me that,” Anuel continued, “I knew I needed to make some changes. Those themes, good versus evil, they were my mark and what separated me from the rest.”

On April 3, 2016, just two weeks after meeting with Hector, Anuel was arrested and held in Guaynabo’s correctional institution on charges of illegal gun possession. Following his biggest musical break yet, just as he was touching the cusp of international stardom, a court judge sentenced Anuel to 30 months in federal prison without bail.

Raised east of San Juan, in the Puerto Rican city of Carolina, Anuel AA has a lot in common with many of my favorite MCs: he’s charming, resolute, and lyrically gifted, yet marred by a criminal past, complicit misogyny and the constant struggle between right and wrong. “I had no choice but to carry those weapons with me, because of the issues I had on the street,” the rapper said to VIBE Viva over the phone, while quarantined in Miami. “I thought to myself I’d rather be locked up than found dead.”

Indeed, Anuel had evaded his probable demise when he was nearly abducted and landed right behind bars months later, fulfilling a prophecy that cost him both his freedom and a flourishing start at the tipping point of trap music en Español. “I was being forced to reckon with all the bad things I had done for money in the past,” Anuel expressed, regretfully. “I started reading the Bible for the first time and realized that my talent and blessings came from God, not anywhere else.”

Anuel had begun to take music seriously around the same time his father, José Gazmey, was laid off from his coveted A&R position at Sony Music. With his back against the wall, a scrappy Anuel left home at 15 and began to engage in felonious activity to help provide for his family and finance his music endeavors.

Like many rappers on the island, Anuel was influenced by popular culture and trends on the mainland, most discernibly by contemporary trap. Anuel understood the genre’s synonymy with street life and the drug enterprise and immediately took to Messiah El Artista, a Dominican-American rapper VIBE profiled for championing Spanish-language trap music all over New York.

“I figured if Latin trap was doing well in New York, it was for sure going to pop in Puerto Rico,” said Anuel, who had signed with the Latino division of Rick Ross’ Maybach Music Group the year prior to his arrest. “I spent about a month in New York before I returned to Puerto Rico. Then I started to release all the songs I had, one by one, and they began to gain popularity.”

While artists like J. Balvin helped breathe new life into the reggaeton genre in Colombia, Anuel wanted to spearhead a movement in Puerto Rico with a sound all their own. “I recorded the ‘Esclava’ remix with Bryant Myers and it might not have taken off worldwide, but it became a huge trap song in Puerto Rico.”

Akin to the heydays of reggaeton, an Afro-Caribbean genre-fusing hip-hop and reggae that originated in Puerto Rico, trap music was considered lowbrow and was heavily criticized for its vulgarity, violence, and explicit lyrics. Puerto Rican critics and artists alike had very little faith in the music’s potential and therefore denounced it. “DJ Luian, who is like a brother to me, couldn’t understand why I wanted to put all my energy into music that none of our artists wanted to sing.”

“Reggaeton went dormant for years,” he continued. “It was necessary to make trap music, because it felt like reggaeton was stuck in another era.” A self-described student of the late and oft-controversial Tupac Shakur, Anuel thought reggaeton had reached its pinnacle and believed Latin trap would be its successor.

Songs like “Nunca Sapo,” where Anuel channels Rick Ross’ Teflon Don ethos and spits a grimy slow-tempo flow over a sinister 808-laden instrumental, helped put a face to Anuel’s little-known name in the US. On cuts like Farruko’s “Liberace,” Anuel speeds up his delivery for fun and plays on the “Versace” rhythm popularized by Migos, who all hail from Atlanta—the widely credited birthplace of trap music.

For Anuel, whose life mantra “real hasta la muerte” is now a famous hashtag, music aspirations had little to do with radio play. Anuel, 27, was largely concerned with dominating the digital space, especially while incarcerated. Despite his arrest, he continued to release music from behind prison walls while his team fed his massive following up-to-date content.

Hear This Music CEO, DJ Luian heeded what Anuel was trying to accomplish and began to work with Bad Bunny, the Latin Grammy-winning artist and star voice of the current Latin trap movement. “When I was locked up, Luian helped develop Bad Bunny and he basically became in charge of keeping trap alive while I was away,” said Anuel, who ironically came under fire recently and was accused of throwing shade at Bad Bunny for the video treatment of “Yo Perreo Sola,” in which the rapper-singer dresses in drag as a stance against toxic masculinity.

“I couldn’t believe something like this was going viral,” Anuel interrupted anxiously before I could expound on a question concerning their relationship. “It looked like it was something that was edited or put together to make my Instagram posts read that way. I immediately texted Bad Bunny about it and he was like, ‘Don’t worry, people are always going to be talking sh*t.’”

Anuel considers Bad Bunny a genius at what he does and maintains that despite not knowing each other very well, he and his fellow compatriot are friendly collaborators with a working rapport: “When he and I do a new song together, what will people say then?”

Today, the collective jury will reach a verdict upon listening to Anuel’s newly-released sophomore studio album Emmanuel, where fans will find a track titled “Hasta Que Dios Diga,” a sultry, mid-tempo reggaeton number. Fans can expect to hear a star-studded project riddled with guest features, including Tego Calderón, Daddy Yankee, Enrique Iglesias, J. Balvin, Ozuna, and Karol G, to name a few.

Discussing life during a global pandemic, Anuel spoke fondly of his partner-in-rhyme, Colombian singer-songwriter Karol G. “She’s the love of my life. She’s been there with me through the good and bad. People who really love you are the ones who stand firm by you when things are bleak. In my toughest moments, Karol was there. She’s shown me how to be a better man,” he gushed.

“Karol comes off as super feminine—which she is, but Karol also has a really tough masculine side,” Anuel laughed heartily on the other end of the line. “She rides motorcycles and likes taking them up these crazy hills. She rides jet skis too! She’s like a dude, haha. We work well together and we give each other advice all the time.”

The pair are making the most of quarantine life in South Florida, releasing a self-directed and self-shot music video for their joint single “Follow,” a reference to flirting over social media in the era of social-distancing, the idea that shooting one’s proverbial shot can lead to a budding romance.

On July 17, 2018, Anuel dropped his debut studio album, Real Hasta La Muerte, hours before he was released from jail. By September, the RIAA certified his introduction to the game platinum, garnering the attention of Roc Nation artist Meek Mill. When the Philly wordsmith released his fourth studio LP in November of the same year, followers were geeked to learn Anuel had earned himself a place on Meek’s highly anticipated Championships album with “Uptown Vibes.”

I always wanted you and anuel aa to make a track together bc i feel like he’s the meek mill of spanish trap , how was it working with him ?

— Nagga (@naggareports) December 17, 2018

“Recording with Meek Mill for me was like when Allen Iverson played with Michael Jordan for the first time,” Anuel said, singing praises about their first-ever partnership. “I’m a huge fan of Meek; when his music took off I was still in the streets, so I related and identified with a lot of the things he was saying.”

“Meek doesn’t understand a lick of Spanish,” he mused in jest, “but he’s always with a bunch of Latinos. When I speak to him he says, ‘I don’t know what you’re saying, but my Spanish [speaking] ni**as tell me you be talking that sh*t!’”

Anuel leveraged his knack for storytelling and released “3 de Abril” earlier this year, an emotional freestyle about the day he was arrested and a graphic snapshot of his trials and tribulations.

“I did things without caring about the consequences. I thought I was a man because I was street smart. Now I know what it’s like to lose everything, so I wanted to talk more about my life and the experiences of me and my family,” Anuel described the inspiration behind the song.

Following the release of “3 de Abril,” Anuel again turned hip-hop heads when he and Lil Pump shared a fiery audiovisual for their collaborative effort “Illuminati,” stamping Pump's first new song since summer 2019. This year, Anuel also has songs with Colombian pop empress Shakira (“Me Gusta”) and with the late Juice WRLD (“No Me Ames”).

Albeit Anuel and Juice WRLD never got to meet in person, Anuel learned about the Chicago rapper from listening to his singles on the radio in jail. “The same year I won Billboard Latin’s Artist of The Year award, Juice WRLD won New Artist at the American Billboard Awards. We ended up recording the song after that but held off on releasing it for a bit because he and I had respective singles coming out at the same time,” Anuel explained.

“By the time we were finally ready to premiere it, Juice WRLD had passed away. We were never able to record together in person, but at least we got to feature him on the video. I know the tribute gave his fans and family some needed strength.”

Less than 30 minutes have gone by and already I am forced to wrap my conversation with Boricua’s burgeoning superstar:

Anuel, explain “real hasta la muerte” for me. Why exactly is this mantra of yours so important?

“I can’t betray anyone. I don’t know what it’s like to really betray someone. I’m very loyal to my circle, my family, and those I hold close to me. Being real is what keeps me humble. It doesn’t matter how much money I make or how much I accomplish. What’s critical is staying real to myself and keeping my feet on the ground. That’s what helps keep me going.”

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This interview was translated from Spanish to English and has been edited and condensed for clarity.