"It was a way for me to start recording a show with my friends. It became like a private space with other people. It was very cathartic," Ossé told Billboard in an interview in September, much of which has been previously unpublished. "[There] was no thought about making a living out of it, as much as, 'How could I compress from all the stress, and especially the corporate PTSD, I developed from years in the music industry?' ... I just knew in my gut it was going to turn into something."
Premium Pete, a Combat Jack Show regular, credits Ossé as the first hip-hop podcast host to land top stars and present interviews in a professional way. "Nobody was doing what we were doing. We sat down with D-Nice, Ice-T. Chuck D for four hours," he says, comparing Combat Jack to earlier hip-hop podcasts by established radio DJs in New York. "[Those DJs] were on Hot 97. How hard is it to take somebody from a morning show into another room and do a [podcast] episode? We had to build up. We used our connections."
Born in Brooklyn to a mother who was a Haitian immigrant, Ossé fell in love with hip-hop at an early age. He lacked musical talent, however, so he drifted into law, attempting to be close to the culture without actually performing. (Although he did appear in 3rd Bass' classic "The Gas Face" video.) "He conceded in later years, the whole reason he wanted to do it was to be around the music, and he couldn't rap," Morrow says.
Ossé attended Cornell University, then Georgetown Law School, and worked in the business and legal affairs department for influential hip-hop label Def Jam Records. Later, he formed a law firm with fellow attorney Ed Woods, who, in a tragic coincidence, died earlier this week. Ossé represented key figures such as Damon Dash, who co-founded Roc-A-Fella Records with Jay-Z, as well as members of Combs' Hitmen production crew.
He stopped seeing clients in 2004 and switched to more creative endeavors, including a blog about his favorite music and a book called Bling: The Hip-Hop Jewelry Book. But it wasn't until he discovered podcasting that he made his post-law career click, as he applied his gift of gab and easy manner with celebrities to a talk-show format. The show became the flagship of a new podcast network, Loud Speakers, drawing hundreds of thousands of listeners as well as major advertisers, and led to spin-off shows such as Fan Bros and In the Mix, some of which have drawn as many as 600,000 listeners per episode.
"He was comfortable having bookish, intellectual conversations, and he was comfortable having conversations with street guys," Morrow says. "He could go either way and be authentic with it. People could connect with him from a lot of walks of life."
The Combat Jack Show recently spun off an acclaimed, multi-part investigative series on late 50 Cent and Mariah Carey manager Chris Lighty. Mogul, a 60 Minutes-style story, inspired Ossé to create more unexpected podcast content. "I get caught up in the hype," he told Billboard. "There was a point we were No. 2 on Apple Podcast, and the only show in our path was Malcolm Gladwell -- I became so concerned with getting that No. 1 spot. . . . You want to be No. 1, but at the end of the day, what did it mean?"
About a month after speaking to Billboard, Ossé announced he had colon cancer. ("I got hit with some real life shit.") He made no reference to illness during his interview with Billboard. "I have to strike when this is hot," he said at the time about his growing podcast empire. "As a matter of fact, I feel forced to go harder."