The moment I met Reggie Osse I knew he was special…a leader…a thinker…Ivy League…incomparably confident and charismatic…a hip-hop head…a man of the people—all people, but he was so f**king proud to be Black…and a man that just made it all fun.

The year was 1992 and the place was the island of Jamaica. I was there along with hundreds of other law students and entertainment lawyers for the Black Entertainment and Sports Lawyers Association’s annual conference. I was 23 years old. The entire conference took place at one hotel and it wasn’t expected that attendees would leave the property. I was in front of the hotel speaking to one of my fellow University of Virginia Law School classmates, Tonya Lewis (she would go on to marry Spike Lee) and seemingly out of nowhere, a Jeep with no top and no doors pulls up blasting hip-hop. The driver was a brown skin brother rocking Ray Ban Aviator sun glasses, no shirt, cut up like an NFL player, a big tattoo on his elbow (nobody Black had tattoos back then lol) and Buddhist beads around his wrists and neck. No, I had never met a brother like this before—that was for sure. He was smiling from ear to ear and after pulling the stick shift out of gear he said, “Y’all wanna go check out the island?” Tonya laughed and said to me, “Let me introduce you to my friend Reggie” and that’s how it all began.

After the introductions, we hopped in the Jeep and sped off into the mountains of Jamaica. I had no idea where this guy Reggie got the jeep or what gave him the audacity to think he could whip that thing on Jamaica’s dangerous roads, let alone know where the hell he was going (there was no GPS at that time) but he wasn’t fazed at all. Reggie Osse was never fazed.

I recall Reggie’s first stop was at a bar with a live reggae band…all I remember is super size Rasta joints were blowing and Red Stripes kept coming and coming. The conversation was amazing. We were all young, gifted and Black. We all wanted to do more with our education than go corporate and we all understood that, at that time, the entertainment and sports industries represented the best chance to achieve success without compromising your Blackness and to help Black artists and Black people.

After a couple hours, Reggie let us know it was time to go. He had a couple more stops for us. Driving through those mountains I remember thinking about Reggie’s spirit. In full disclosure, I was a bit cocky and arrogant back then…I thought I was the shit…I was in a JD/MBA program at a top ten school. I was a member of the best Black fraternity, Kappa Alpha Psi (Reggie was a member of Phi Beta Sigma) and in my mind this was like Batman meeting Superman. It wasn’t often that I met people that impressed me. This Reggie guy was impressive in every way and I immediately admired him and respected him. Fundamentally he was just a good person. I know he saw that in me too because later he would put his name on the line for me many many times and I never let him down. In many ways we were so similar and in many we were so different but in the end, game recognized game. This time the drive was surreal–we talked less and listened to Reggie’s CD of some of the hottest New York hip-hop music I had ever heard. None of us realized it at the time, but a new wave…more like a tsunami was forming and it would change the world forever. That wave would later be known as the golden era of hip-hop and we were surfboard ready-to-ride—timing is everything.

Reggie made a sharp left turn into the driveway of a small house with a sign on the front that read “Ms. Browns.” We knocked and a beautiful old woman, Ms. Brown, greeted us and sat us down at a dining room table. Reggie stepped out and had a private conversation with Ms. Brown and they returned with tea cups for all of us. Ms. Brown proceeded to pour us a drink from an unlabeled brown bottle. I remember asking Reggie, “Yo man what is this?” and he responded “Its tea…you’ll love it.” I drank the tea—at first I thought it was real tea, then I thought it was maybe some type of steamed marijuana leaf tea but the taste was totally unfamiliar. I drank it all though. I didn’t want to offend Ms. Brown, I didn’t want this Reggie Osse guy to think I was a square…so f**k it, I drank it all. Ms Brown then brought out some Red Stripes..I presumed to wash down the weird after taste. We had a few more Red Stripes and again we were back to amazing conversation. More trees were blowin and again, the Red Stripes kept coming and coming. Then things started to look, sound and feel different. Everything kinda shifted from surreal to sublime. I asked Reggie again, “Yo man…what KIND of tea was that?” and with that ear-to-ear smile he responded, “Mushroom Tea.” I looked at Reggie, smiled, shook my head and went with the flow.

I don’t remember much after that. I know I thought the psychedelic trip would never end and admittedly I was straight trippin. Reggie would tell this story for the duration of our friendship. It was our bonding moment.

I woke up in the back of the Jeep feeling much better as we pulled up to the hotel. My plan was to say my thanks and goodbyes to Reggie and Tonya and slide off to my room for a good night’s sleep. No dice. Reggie wasn’t having it. He proceeded to take us to big suite in the hotel and when he opened the door there was a private party rockin full tilt. I couldn’t believe it. More trees blowin, more Red Stripes, a DJ and people partying to great music. Reggie’s arrival electrified the entire party and what I remember most from there is that Reggie took the time to introduce me to everybody in the room. I would later realize that these people were basically his family: Louise West, Bob Celestine, Ed Woods, Matt Middleton, Gwen Niles (who would later go on to marry Ed Woods) and so many other law students and lawyers that would I would encounter and become friends and or colleagues with for years to come. That was Reggie. Unselfish. Caring. Always concerned about helping others.

Years later, after graduation, I moved from Charlottesville, Virginia to Brooklyn, NY to figure out my career. I knew less than 20 people in a city of eight million but I was determined to find my way. I stayed in touch with Reggie and would see him with his partner Ed Woods at industry events all the time. It is really hard to articulate how special the law firm of Osse and Woods was in the 90’s. All I can say is that they knew EVERYBODY and their network seemed to be limitless.  If something was happening in the city they knew about it.

I had two roommates in Park Slope Brooklyn and we decided to have a house warming party. I ran into Reggie on the street in Brooklyn and he suggested that he host the party. It was around this time that I met his beautiful and super smart girlfriend Akim (who Reggie would go on to marry). At the time I didn’t know what a Reggie Osse party meant but I agreed. By 10PM there were 100 people outside that couldn’t get in. Inside, our apartment was packed with a who’s who crowd of New York City artists, actors, painters, rappers, writers, lawyers you name it. It was really really special. Once again, Reggie had impacted my life by lending a hand.

Years later, as Osse and Woods was thriving, I was struggling to put all the pieces together. I knew I didn’t want to practice law. I wanted to be on the business/creative side of the music industry and possibly film industry. I also needed to make more money because New York City was (and still is) a very expensive place to live.

I called Reggie for advice and he listened. He was busy as hell but he said “Look, I want you to call Gwen Niles…she’s running a new label venture at The Hit Factory and she might be able to help you out.” Weeks later I was hired as an A&R at The Hit Factory, reporting to Gwen Niles. This was a pivotal moment in my career because it legitimized my ears in the music industry and gave me a formal platform to use to move through the streets with authority. I stay in touch with Gwen and I’ll always remember and appreciate what she and Reggie did for me at that time. I would go on to sign an artist to Elektra Records after a serious bidding war that ended with Sylvia Rhone making a 7 figure offer. After news of this deal spread throughout the industry, I was offered a job as Director of A&R at Priority Records/EMI which I accepted. After completing the soundtrack for the movie Training Day, I set out on my own to start Babygrande Records and iHipHop. Who knows how this might have all turned out if Reggie Osse didn’t start this progression by helping me get my first job as an A&R.

As time passed, Reggie and I stayed in touch…we were not best friends but we were kindred sprits, two planets in the same solar system, two players in the same pro league. Our lives seemed to always weave in and out of one another’s at just the right time. Friendships can’t always be valued based on time spent together and or how often you talk to one another. Some friendships just exist and unfold as they are meant to be.

In 2009, iHipHop was looking for hosts for our release party for Wiz Khalifa’s “Deal or no Deal” album. Coincidentally, I had recently had a catch up call with Reggie and he brought me up to speed on his blogging as Combat Jack. Reggie told me that he was still finding his way since leaving his law practice but that he was incredibly happy and excited about music again. He also told me how happy he was about his wife Akim and his family and how far they had made it. Reggie loved his wife and family from the bottom of his heart. We talked a lot about marriage, having kids (he had four, I had two), the proverbial mid-life crisis and about maintaining our love for hip-hop as we age.

I asked Reggie if he would be interested in hosting the show and he loved the idea. We agreed that he would reach out to Angela Yee (I knew Angela as GZA’s former manager’s on my Babygrande label) to co-host and Angela agreed.

Wiz Khalifa’s release party turned out to be a monumental night in my career. Our album with Wiz hit #1 on iTunes the night of the party. We had broken an artist who would go on to become a super star and I got to share that moment with Reggie. I was proud that I had something to offer Reggie. I guess I had always admired him so much it also felt good that Reggie saw me shining after he had helped me so much and that he was a part of it.

Weeks later, Reggie came by the office and met my whole team. Everybody loved Reggie off the rip. It was like a totally different office when he walked in. Sh*t talking for hours…my favorite memory was seeing my guy Ruddy Rock and Reggie playing game after game of chess trying to see who was the best—two Brooklyn guys goin at it. Most of my team went on to develop their own independent relationships with Reggie which made me very happy.

I sat down with Reggie and he proposed the idea of leaving XXL and coming over to iHipHop with Dallas Penn. He said he felt that he was worth more than XXL was willing to pay him. Without hesitation, I agreed and accepted his fee without negotiation. After all he had done for me, that was the least I could do and it was important to me that he knew that I saw it that way. This is they way men communicate some times—through actions and not words. Even still, I knew Reggie had some kind of chess move in mind with this move lol. The next day several blogs came out with stories like “Combat Jack bolts XXL for iHipHop” and “iHipHop pays twice as much as XXL”. I knew Reggie well enough to know that his reasons for coming to iHipHop were multi-dimensional but I loved the guy and that was that. Reggie wrote an article on iHipHop  about the whole thing which re-reading today brings tears to my eyes. I’m the “Black fella” he talks about.

Reggie and I had many conversations during his time at iHipHop. I cherish this time now as I look back at it. We talked about how far he could take Combat Jack: radio, video interviews, television, podcasts, lecture series and more books. Life brings many unexpected turns and I truly believe that Reggie needed me at that moment and I was honored and proud to help him as he helped me. I was riding high from our success with Wiz Khalifa and he needed some of that energy. I truly believe that the time he spent with iHipHop and our conversations gave him the boost and the blue print to step out and create his own empire as he saw me doing.

The time came and we sat down and he let me know he was venturing off to start a podcast as “The Combat Jack Show” and I was ecstatic about it. In Reggie’s mind, his vision for Combat Jack had expanded and it was time for him to go get that bag. He had found his lane and wasn’t looking back.

I didn’t spend much time with Reggie after that. He was chasing his dream with hyper focus and I understood that. Combat Jack became a celebrity which brought Reggie money, fame, pressure and responsibility. I’m sure this brought him new challenges that we never had a chance to share.

I’m in Thailand as I write this—working with an Executive Coach to prepare me for some big things on the horizon. The day I landed I thought about Reggie twice: first, my female cab driver asked me “You Buddah?” pointing to her Buddhist necklace hanging from her mirror and second, my Executive Coach told me that in addition to fasting for 14 days that I would be cleansing my colon daily. Later that night I received an email from a friend in LA saying Reggie had died from Colon Cancer. Like so many, I never got a chance to say goodbye.

I will miss my brother. I learned so much from him. He helped me so much when he didn’t have to. I can say unequivocally, I will do everything in my power to be there for his wife Akim and their four children. I will also carry Reggie’s spirit with me as I push and protect hip-hop in my lifetime.

Rest easy my friend.

Chuck Wilson

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