Fredo Santana

Fredo Santana, born Derrick Coleman in 1990 in Chicago, was a central figure in the city's drill scene of the early 2010s, known for his gravelly delivery and unfiltered depictions of street life. As the older cousin of Chief Keef, he served as co-CEO of Glory Boyz Entertainment before founding his own label, Savage Squad Records, through which he released much of his solo material.

His debut album, Trappin' Ain't Dead, arrived in November 2013 and charted on Billboard's Top Rap Albums while reaching high positions on iTunes' hip-hop chart, cementing his standing as one of Chicago drill's foundational artists. Songs like Jealous, My Lil' Niggaz, Gang Bang, War and Dope Game captured the raw, menacing sound that helped define the genre's early aesthetic, built on dark production and blunt street narratives.

Instantly recognizable by the cross and teardrop tattoos on his face, Fredo Santana became one of drill's most authentic voices before health struggles slowed his output in his final years. He died in January 2018 at age 27 following a seizure related to epilepsy, leaving behind a catalogue that remains foundational listening for understanding Chicago drill's origins.