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Reggie Ossé, 53, hip-hop lawyer turned podcast pioneer

By Jonah Engel Bromwich New York Times  

NEW YORK — Reggie Ossé, a knowledgeable and boisterous broadcasting personality better known as Combat Jack who parlayed his experience in hip-hop into a podcasting empire, died Wednesday in Manhattan. He was 53.

The cause was complications of colon cancer, said Chris Morrow, chief executive of Loud Speakers Network, the podcast group that has nurtured the careers of a generation of hip-hop broadcasters, which he founded with Mr. Ossé.

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Several generations of rappers, radio hosts, and journalists mourned Mr. Ossé's death. In an interview Thursday morning, Atlanta rapper Big Boi called him “one of the brightest guys I’ve ever known” on music and black culture.

“He was just a very intelligent curator of the culture,” Big Boi said. “He wouldn’t ask the same questions that every interviewer would ask. He was like one of our friends. He treated you like a friend.”

Mr. Ossé came of age in New York in time to see the rise of hip-hop from a local phenomenon to a worldwide craze. Working as a lawyer at Def Jam, an institution as important to rap in the early 1990s as Andy Warhol’s Factory was to art and music in the 1960s, he crossed paths with Jay-Z, Puff Daddy, and other early rap royalty before they were famous.

After walking away from the entertainment industry, he reinvented himself when the social web was in its infancy. He worked as a blogger under the pseudonym Combat Jack, then began to use the name as a podcaster in 2010.

As with Marc Maron’s candid conversations with comedians on his podcast, Combat Jack was able to coax hip-hop luminaries into revealing parts of themselves that they had never shown in public.

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“The amazing thing about Combat Jack’s life is that he had two successful runs in the hip-hop business,” said Peter Rosenberg, a DJ with the New York rap station Hot 97. “One as an entertainment lawyer back in the day and then a second run as a podcaster where he became this real authority about everything that was hip-hop culture and history.”

Reginald Joseph Ossé was born on July 8, 1964, in Brooklyn. Raised in Crown Heights, he took an early interest in the arts and applied to Cornell University’s fine arts program with the help of a high school teacher. Frustrated with the program and impressed by a relative who worked as a lawyer, he decided to pursue a legal career. After graduating from Cornell, he attended Georgetown Law School.

“He was a fan above everything else,” Morrow said. “The reason he got into law in the first place was he just wanted to be around the culture and the music.”

After graduating from Georgetown, Mr. Ossé began working at Def Jam at a time when hip-hop was still young and artists and their representatives were learning how the business worked on the fly. Bobbito Garcia, a co-host of the early hip-hop radio show “The Stretch Armstrong and Bobbito Show,” met Ossé when they both worked at Def Jam. Garcia described him in a phone interview as having a “vivacious, hilarious, bugged out, a little to the left type of personality that I fell in love with.”

Mr. Ossé later formed a firm with another lawyer, Ed Woods (who died earlier in the week). One client was Damon Dash, who worked with Jay-Z to found Roc-A-Fella Records. Mr. Ossé was involved in shopping Jay-Z’s debut album to various, ultimately uninterested labels. Years later, he met with 50 Cent, who was then unsigned but who calmly explained how he planned to take over the music industry.

When Mr. Ossé began the Combat Jack radio show in August 2010, he began attracting listeners through his in-depth conversations with such figures as Dash, a legendarily terse interviewee who was unusually forthcoming with an old peer. Mr. Ossé also became familiar to many listeners on Twitter, where his unguarded opinions attracted legions of fans and no shortage of critics.

His show was one of the first to cover hip-hop in such depth. As it gained popularity, eventually drawing hundreds of thousands of listeners, Mr. Ossé took on the role of elder statesman and developed a reputation for generosity toward his younger counterparts.

In an episode of his show posted on Halloween, he talked about his illness and emotionally thanked fans for their support before reverting to character, making jokes about his colostomy bag and the amount of weight he had lost.

In the rap industry, Combat Jack commanded respect, Jason Ryan Lee, an editor at the entertainment website Bossip and a frequent guest, said in an interview: “Amongst the artists, among the executives, among other journalists,” he said, “Reggie Ossé was a name that really mattered.”