Originally posted December 20th, 2017
If you read any bio about me, it’ll say some variation of “20-year industry veteran…”
I’ve been in the entertainment industry my entire career, but it never would have happened without these three men: Ed Woods, Reggie Ossé aka Combat Jack, and Matt Middleton.
I started in the combined law offices of Ossé & Woods / Middleton & Niles, at 60 East 42nd St, where every major artist and producer of the late ‘90s was either represented or at some point did a deal with a client. The Shyne deal? Ossé & Woods. N.O.R.E.? Middleton & Niles. The entire Bad Boy Hitmen roster of producers? Ossé & Woods. Ruff Ryders, Roc-a-Fella, Violator…. Name any label, any artist, any producer that was at the height of hip-hop from ’97 through the early ‘00s; these guys played a part.
They were hungry and smart as hell and unfuckwittable. With their combined relationships and connections, plus sheer drive and energy, they were young masters of the entertainment law universe. Where Ed was a fast-talker who could be bombastic and over-the-top, Reggie was steady and methodical; two very different personality types that played off of each other not unlike a professional comedy duo. Already a husband and father, Reg would drop career and life jewels at what felt like random moments, would take time to ask me about my future plans, would caution me against pitfalls (like dating clients…and if I was going to date a client, how to make the best of it.) The joint firms were at one point the largest black entertainment law practice (in terms of clients and billing) in the country. Ten years later and that office would have been ripe for Monday nights on VH1. (Ed actually did dabble in reality TV a bit, most recently on WeTV’s Money. Power. Respect.)
Their passion for the business in turn lit a fire in me and helped me realize that I loved the game and the culture — but didn’t want to be buried in the paperwork! I pursued a career on the creative side instead. I called Harve Pierre, a client, and asked if I could intern with him at Bad Boy. My story continued from there.
On Saturday, we were shocked with the news of Ed’s sudden passing. A gregarious personality, always sh*t talking and joking, the idea of him being suddenly gone stunned us all; especially because we’d just recently learned that Reggie was battling late-stage colon cancer.
Then this morning, news came that Reggie had died as well, and all of us who knew them both are collectively stuck right now. Even though we knew what he was battling, Reggie Ossè was one of the most bout-whatever-the-hell-he-said-he-was-gonna-be-about people I knew. When he said he was fighting, I was like “Hell yeah, you’re fighting.” It honestly never crossed my mind that he wouldn’t beat this.
And right after Ed? Did ya’ll have a conference and decide to put the firm back together on the other side? Is there business in the great beyond that Big, Pac & Pimp C need handling? Ya’ll doing deals with Shakir and Baby Chris?
I will never, ever accept that I’m at an age where my peers will die. In my mind, we’re still in our 20s and 30s out here taking this game by storm. The whole world is still at our feet. How is this possible?
As you see the many deserved tributes for Combat Jack over the following days, know that his story started before The Combat Jack Show and Loud Speakers Network. That he was part of the fabric of the business and culture of hip hop in a real, concrete way. That he was part of a team that f*cked heads up when they came in the room and sat at the mahogany conference tables. And that over the years he reinvented himself multiple times, always in ways that would move the culture forward.
Watching Reggie move from law practice to author, then from author to editor at The Source, from there to blogging and finally to the podcast space, breaking new ground and launching multiple platforms — and several new chapters for people — through LSN, helped me to always think about being flexible to adjust with the ever-changing and evolving business of entertainment. Watching him also reminded me to make sure I incorporated my creative passions in whatever I did. He mentored me even when he didn’t realize it.
But also know that it’s deeper than rap. Literally. A practicing Buddhist, Reggie was always warm, gentle, generous and gracious. Always had love, always genuinely happy to see you. Always.
(2018 edit) Reggie’s death made me take a serious look at what #MusicSermon could and should be maybe for the first time since it had become a “thing” five months prior. As I wondered how I could honor his and Ed’s legacies, I realized that continuing to build a platform to tell the untold and forgotten stories in the name of The Culture was the most fitting tribute. Selfishly, I’m so thankful that he saw it building and gave me a thumbs up. It meant everything.
I am thankful for having known these guys. I am thankful for all I learned from them. For the access I gained through them. For the stories I have from them. For this life and business I became part of and learned how to maneuver through because of them.
Each man was truly One of One.
Long live Ossé & Woods. #FuckCancer #WhosYourLawyer
“Internets, you know what time it is: Dream them dreams then man-up and live them dreams, because a life without dreams is black and white, and the universe flows in technicolor and surround-sound. Blaow!” — Reggie Ossé/Combat Jack
PS, If you only read one story about Reggie and his work, read this one.