Courtney Everald Dewar, Jr. was born in New York City to Jamaican parents. His father died when he was in high school. He began rapping in 2009, then known as Jay STEEZ, with his friend Jakk the Rhymer. Together they formed a group called The 3rd Kind. Their first mixtape was titled The Yellow Tape, which included tracks that sampled the popular British virtual band Gorillaz and the final speech from Charlie Chaplin’s The Great Dictator. In the spring of 2011, while still a student at Edward R. Murrow High School in Brooklyn, New York, Capital STEEZ and record producer Powers Pleasant formed Pro Era on their way home from a performance Capital STEEZ had at a local Brooklyn cafe, which a number of friends including Joey Bada$$ and Dirty Sanchez also attended to show support. On February 23, 2012 a music video for a song called “Survival Tactics”, which featured and starred both Joey Bada$$ and Capital STEEZ was uploaded on YouTube, which received positive reviews from many rap outlets, thus gaining Pro Era mainstream fame. Capital STEEZ’s closing verse was named on their list of “25 Of The Best Closing Lines In Rap” by XXL Magazine.[6] He was listed in “The 25 Best Rap Lines of 2012” by Spin. Capital STEEZ released his first solo mixtape, “AmeriKKKan Korruption”, on April 7, 2012 with 14 tracks. The mixtape has been highly acclaimed since its release. A “reloaded” version with seven additional tracks was released on October 10, 2012. The tape now runs 21 tracks in total and features many of his Pro Era teammates, such as Joey Bada$$, CJ Fly, Chuck Strangers, Dirty Sanchez, and Jakk The Rhymer. The mixtape contains production from Madlib, MF DOOM, Free the Robots, DJ Premier, Knxwledge, Ant of Atmosphere, J Rawls, Tommy Mas, The Entreproducers, and production from fellow Pro Era members, Chuck Strangers, Kirk Knight, Bruce Leekix, and even Bada$$ as OG $wank.

Capital Steez committed suicide in the late hours of December 23, 2012. On the night of December 23, 2012, he made his way to the rooftop of the Cinematic Music Group headquarters in Manhattan’s Flatiron District, where he texted a few of his closest friends to tell them that he loved them, and at 11:59PM, posted a tweet saying, “The end.” He jumped off the rooftop of the Cinematic Music Group building later that night. In late April 2013, Joey Bada$$ announced that a Capital Steez album would soon be released. On July 7, 2013, Pro Era released the song “King Steelo” from the upcoming posthumous album. Bada$$ later indicated that an album of unreleased material was scheduled for release. On December 24, 2013, to honor the anniversary of his death, Pro Era released a music video for his song “47 Piiirates” . On August 26, 2016 the official Pro Era YouTube channel released an animated video for the song “Herban Legend”, which premiered at second annual STEEZ Day in Los Angeles, California on July 7, 2016.