Santana benefited from the controversy that his cousin Chief Keef was creating in Chicago rap. Santana’s first debut album was called Trapping Ain’t Dead and it was released in year 2013 under the Savage Squad label. Santana tried to appeal to the same aesthetics that his cousin did. Trap music was a new genre that came from hip hop. It was called Trap Music because it was supposed to sound like the music played in crack houses. Making money about drugs is not a new trend in hip hop. Even in its infancy, hip hop promoted drugs like cannabis and cocaine. The concerning thing about the modern hip hop era is rappers like Santana and Keef are pushing dangerous drugs like crack and cough syrup. Children may look up to them and try to emulate their risky behavior.

Santana didn’t always go by his current rap alias. His first mixtape was under the name of Scary Site and it was released in 2012. The mixtape featured the production of many people include C-Sick, Leek E Leek, 12Hunna, and Young Chop. His second mixtape is called Fredo Kruger and it was released in 2013, featuring rappers like Young Scooter, Soulja Boy, Juelz Santana and Migos. In just one year, Santana raised his profile in the rap game which can be seen by the amount of talent he secured for his second release. Soulja Boy and Juelz Santana of dipset were already well established hip hop acts. Getting the rub from them was a blessing for Santana’s career. He also got to work with Migos before they blew up into the mainstream stars they are today.

In 2013, Santana made a cameo appearance in a music video of Drake’s called Hold On, We’re Going Home. He was not performing musically and instead had an acting role portraying a bad guy that kidnapped the girlfriend of Drake. Even though he did not rap on the song, getting to be in Drake’s music video got huge exposure for Santana’s personal brand.

After the series of mixtapes, Santana felt it was time to release his debut album. The album, Scary Site 2 was released in 2013 and featured guest appearances by Kendrick Lamar, PeeWee Longway, and his cousin Chief Keef along with other members from Glory Boyz Entertainment. Getting Kendrick Lamar to appear on his debut album was a huge positive for Santana. Kendrick is considered to be the king of today’s rap scene. The rapper became an even bigger star when he produced the soundtrack for Black Partner. Santana would be forever grateful to collaborate with a mega star like Kendrick.

In 2014, Santana announced that he would release a collaboration with Chief Keef called Blood Thicker than Water. The second album was a reference to the family bond that Santana shares with his cousin, Chief Keef. Santana also released a third album entitled Walking Legend. Santana integrates horror elements into his image and lyrics which an emerging trend that is common among some of today’s rappers.