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Combat Jack Reggie Osse as he was known to his friends was lying in his hospital bed.
His big belly pressed tight against his blue gown.
His face was gaunt, missing 10 or 15 of the pounds that typically rounded out his cheeks.
It was late October, nearly two weeks after hed checked in to Brooklyns NYU Lutheran Medical Center.
Then the pain went away, so I think Im out of the woods.
Two weeks ago, the pain came back.
Im like,let me get a sonogram.
The sonogram said my liver was inflamed.
Last Saturday, the pain was unbearable.
And we need to do surgery tonight.
And had you not come in today, you might not have seen tomorrow.
Blindsided by the diagnosis but bowled over in pain, he went under the knife.
I still dont know what the fuck they did, but they said they saved my life.
A book, a TV show, maybe a movie,something.
This left him encouraged and hopeful.
Hed been arrogant, always in perfect health, was over 50 and had never had a colonoscopy.
Stage 4, hed heard, but there was no pathology, norealdiagnosis.
Just then though, as if on cue, a hospital resident walked in.
The resident seemed unsure, gave him a number anyway.
It was a better number than expected but still not great.
Mikas eyes turned glassy and wet.
Osse looked on stoically, his eyes wide, his breath steady.
I mean, thats dire, he said, his feet bouncing nervously beneath the blanket.
Thats dire, thats what it is.
He paused, considering things.
But that sounds great to me.
Glass half full, right again, Im sorry, she said, choking up.
No, he said.
Youre a great patient though, she said.
His voice was a whisper.
2017 had been a banner year.
TheCombat Jack Showwas humming along, its library closing in on 450 episodes.
A gig on Sirius XM only helped expand the brand.
I was making more money than I ever made, it was a turning point.
Two years ago, Osse began having personal problems.
In April of 2017 he filed for divorce.
These past few years, I became a super-heavy drinker, he said.
Id wake up in the morning with a shot of tequila.
I was just trying to wrap my my head around this divorce.
I didnt give a fuck about life.
In addition to the booze, he smoked weed, smoked cigarettes, ate poorly.
Then came the pain.
His family doctor said it was stress related,maybethe drinking.
So he made some tweaks.
He got closer with Mika.
He curbed alcohol, tried cleaning up his diet, took up biking.
I just went overboard, he said.
Cancer was going to happen regardless, drinking didnt necessarily exacerbate or accelerate it.
But it cant [have been] good.
In the wake of his diagnosis, Osse was defiant.
The podcasts closing salvo was always the same: Dream those dreams, hed say.
Then man up and live those dreams.
Osse would beat cancer like so many things hed beaten before it.
So Im gonna knock it out.
Uncle @llcoolj told me to knock it out.
So Im gonna knock it out!
But he was antsy and wanted to work.
The next day, as he sat in his living room, his energy was good.
The RA was trying to get me woke, but I just wasnt that woke, he said.
On Friday nights, she would show shit likeBirth of a Nation.
Im like:Were free right now.
I came from the hood, so being at Cornell, I felt like I made it.
It was just ignorance.
He was also particularly reflective about his parents, especially his mother.
I was his son, but he didnt really care for me.
Everything about Osses childhood was an effort to help him level up.
Our shit wasnt middle class, it was working class, he said.
Parents that worked 365 to maintain a shot at the American Dream I was that shot.
Fuck you, nigger.
Youre a fucking nigger.
Nigger, nigger, nigger.Hes just screaming at me.
At that age I wasnt really traumatized by race.
I was just a kid.
As he grew older, his worldview grew increasingly darker.
Shit was likeThe Warriors, he said.
It was fun, but it was so lawless and primal.
I was forced to grow up quick.
But RFK was a small, specialized Catholic school, one classroom for each grade.
At the end of the year, the students had the option to take an international class trip.
Osse went to Italy one year, Spain the next, expanding his worldview.
[On those trips] we were smoking weed, going to wine tastings, he said.
It was a crazy school.
Crucially, too, there was music funk, rock, soul, even disco.
Hip-hop, though, is what changed his life.
My friend kept telling me rapping, you know, rappers?he said.
Imagine trying to explain rap and youre one of the only people who experienced it.
I felt these kids were talking to me.
He recorded a few basement tapes, yet remained convinced he didnt have much talent.
Instead, he gravitated toward sketching and painting.
It was just a bunch of trust-fund kids, he said.
Postgraduation, he went to law school at Georgetown.
Youre giving up on your dreams, youre fucking up,he said Ms. Minter told him.
I was like,yeah, but I gotta find a way to come back to Brooklyn.
As this black kid, I dont have the luxury to be just hanging out in art galleries.
It wasnt like now, where you could finesse anything.
It was a sense of survival.
Rubbing elbows with his heroes, you couldnt tell Osse he hadnt made the right choice.
Once you met them you never forgot who they were.
It wasnt real for me until then.
The only celebrities I had ever seen were on TV.
I studied Public Enemys contract, he said.
And he wasnt getting rich himself.
In fact, he wasnt making much money at all.
Andy, this Jewish attorney, said:Russell, pay your black people.
She knew I was the future.
Working with Louise opened my whole world up to black entertainment law.
Wests intuition was right.
By 1995, hip-hop was booming, and Osses client list was growing.
So with a partner, Ed Woods, he set up his own firm, Osse-Woods, LLP.
and Sean Diddy Combs.
But it was another client that could have been his big score.
Damon Dash started managing Jay-Z and we did everything to push this guy, Osse said.
He was every bit as confident, as arrogant, whatever you want to say Jay-Z is today.
After Osse helped Jay-Z get his first record deal, Roc-A-Fella ditched him for another attorney.
This scenario played out repeatedly as artists climbed the food chain; the disloyalty was grating.
I wasnt fulfilled anymore, hetold HipHopDXin 2015.
I just decided that I needed to be in control of my destiny.
I was just catering to everybody elses dream as an attorney.
I knew there was something out there for me than just being an attorney.
And I had a voice too.
In the early aughts, file sharing sent the record business into a tailspin.
Hip-hop blogs were then in their infancy; loose and chaotic, they had a youthful energy.
To Osse, it was heaven.
We were basically just fucking around on the internet, Crawford recalls.
It was the kind of thing I wished were in magazines like theSourceorXXL.
At some point it went from being a hobby to being his lifes work.
The podcast just took it to a different level.
Watching it unfold, I was really surprised to see it become as big as it did.
After launching his own blog, Daily Mathematics, theCombat Jack Showstarted in 2010.
During a Twitter spat about the direction of the morning show, RosenbergthreatenedOsse.
It was all the ammunition Osse needed.
Dallas Penn, another blogger, served as co-host.
It was loose and unscripted, more like friends in a barbershop than a choreographed interview show.
Seven years later, with its blend of interviews and commentary, the show had become a hit.
Guests ran the gamut, from hip-hops past and present, plus filmmakers, activists, and cultural critics.
When Osse asked the questions, the guard came down.
Consider Public Enemy front man Chuck D airing out his own grievances with Hot 97.
Or David Banner talking about his sex addiction.
Damon Dash opining about the culture vultures whod infiltrated the rap game.
DeRay Mckesson discussing tweets hed drafted in case he died during the 2014 Ferguson protests.
J. Cole chatting about stepping away from the limelight to produce his best album,2014 Forest Hills Drive.
Hes just a fan at heart.
This is why wide swaths of listeners could relate to Reggie Osse.
The show was intimate, often hilarious, frequently controversial and always smart.
Thats what hooked Morrow.
Prior to that, I always felt like an adult crashing the kids prom.
Even terrestrial radio jockeys were impressed.
He wasnt afraid to disagree with you and wasnt afraid to ask tough questions.
He also contributed enormously to the growth of podcasting, period.
There was always this feeling that podcasts were for middle-aged, affluent white guys, Morrow said.
It was an uphill battle and only recently had it gotten easier.
Reggie used to always ask me,Yo Pete, are they listening?
We just turned on the mics and were playing fucking games.
[Then] we were like rock stars.
Were taking pictures with people, signing autographs.
There wasnt much money then, but theCombat Jack Showbecame abrand.
Fans loved the show at different times for different reasons, but Osse was the only constant.
There was noCombat Jack Showwithout Combat Jack.
Im probably going to live to my 90s, he said in the living room.
As the day wore on, people began pouring in, wanting to see how Osse was doing.
His son Chi was there too.
Did you start chemo?
I gotta heal, Osse said.
I still have a big scar, a shit bag.
Dont get too close to me, I got shit in the bag.
Didnt they say you have to start chemo immediately?
Well, chemo kills me, he said.
So I have to heal.
Did they say that or …
Thats my understanding it might take me like three months to really heal.
Thats a long time, Chi said.
Osse turned now, talking to the room, but also his son.
And understand, your dad is the same way.
And Im not settling for anything.
Im not jumping into chemo, because I have to get healthy, thats the bottom line.
Ive only been home four days and Im exhausted.
I gotta get my wind back, I gotta get some weight on me.
I feel like people start immediately though.
It depends, a friend said.
If they catch it early.
But they didnt catch it early.
Theres a pacing, Osse said.
Well,there isa rush.
But theres no two week, three week, one month, two month rush.
I gotta get on my feet.
Chi looked at him then, knowing his dad and all his quirks in ways that only sons can.
Dont be lazy with it, Chi said.
Osse had his reasons for not being pressed on chemotherapy.
He was a devout Nichiren Buddhist, and believed far more in holistic healing than Western medicine.
He also didnt know yet if chemotherapy was an option.
Perhaps the cancer had already spread too much.
On November 13, only a week after leaving the hospital, Osse was headed right back.
With Mika in tow, he was to meet an oncologist there and plot next steps.
But when he arrived, things immediately went off the rails.
Then he couldnt tell me if it was Stage 3 or Stage 4, couldnt tell me anything.
It was like something out of a Jerry Lewis movie.
So Osse grabbed his medical records and headed for the exit.
Maybe hed check in at Sloan Kettering.
It had only been two weeks.
The Roots sent me a get-well card, he said.
It said:You got this Combat, lets go.
Its fun, seeing the best of your peers.
Like LL Cool J, my first day in the hospital, he calls me.
Im like that proverbial kid who is sick and all his heroes start reaching out to him.
How does my current predicament get me so much more love, the kind Ive wanted for a while?
He presented a new way to hustle I dont know that the world really knows that.
Hes one of the founding fathers of podcasting.
Osse was on a liquid diet and he was weak.
Confined to the bed, where he sat shirtless, a big surgery bandage still covered his lean torso.
His weight had dropped considerably.
But he died in 2016, so that angle was out.
He couldnt talk long.
The hiccups came from his gut, rocketing up and out of the body.
Soon, he could no longer speak.
Only when she began crying hysterically did he agree.
They called an Uber, got to Beth Israels emergency room, and put him in the ICU.
Whatever affairs you might have, get them in order.
There were issues with his kidneys his potassium levels were low, and they were no longer functioning properly.
Hopefully itd keep him alive.
Periodically, hed whisper to Mika, who had been there since hed been diagnosed.
He laid flat, his head back, cradled in her hands.
I wondered how long this would continue.
I wondered if he knew I was there.
Then his head went back further, he appeared unconscious, but was not.
He wanted to say something.
He smiled, teeth showing, eyes bright.
He put an outstretched arm in the air.
Then he flashed a peace sign.
TheCombat Jackarchive is still availableto stream.
