‘Star Stories With Touré’: That time I almost went bankrupt playing poker with Jay-Z

OPINION: In my new animated series, “Star Stories With Touré,” I share some of the craziest moments I’ve lived through while interviewing celebrities.

Editor’s note: The following article is an op-ed, and the views expressed are the author’s own. Read more opinions on theGrio.

Jay-Z is a really interesting person to hang out with, which is why he’s the center of the first episode of my new animated show, “Star Stories With Touré,” which you can find at https://thegrio.com/starstories

On this show, I tell stories about crazy experiences I’ve had with superstars. The thing about hanging with Jay-Z is you have to watch your wallet. He’s a rich man, and he does rich-man things. You want to hang because he’s Jay, but you could spend way more than you should. 

That said, the trouble I ran into was not Jay-Z’s fault. It was all my fault. See, sometimes journalists act like a fly on the wall and just report what they see and don’t get involved in the story. I was like that for years. But then I realized that it made for a more engaging story if you get involved and explain the story from the inside. I was inspired by legendary writers like George Plimpton, who once briefly played quarterback for the Detroit Lions so he could write about it, and Hunter S. Thompson, who made everything he wrote about himself. I wanted to influence the environments I was in so I could use them to create the most realistic portrait of the person. For example, if Jay-Z is playing poker with his friends, what’s the best way to write about that? Standing behind him or being in the actual game? But being in the actual game means putting down your money.  


The year was 2001, back when Jay was worth about $50 million, a pittance compared to what he’s got now and also a very tall mountain compared to what I have. I hung out with him for the better part of a week, working on a story for Rolling Stone, and that night, at the Trump Tower in Manhattan’s Columbus Circle right near Central Park, I met him and the boys as they played poker. I watched for a while but I wasn’t getting good stuff so I said, let me play. It was a table of rich guys from the music business and the streets. I am neither rich nor street nor good at poker. Joining the game was, as a writer, a great call. I could now get insights into Jay-Z that I couldn’t get by just standing there watching. But in some ways, it was a terrible decision. Worse for me, that was just the first of many bad decisions I made that night. Look at this tangle of thorns.

I asked to play without even knowing what game they were playing. I just wanted to be in for the good of the story. The game was called Guts. You’re dealt two cards and you keep them secret. That’s it. There’s no flop, there are no more cards dealt. I have two hidden cards, and I have one chance to decide if I’m in the hand or not. The only info I have is what cards I have. If you have the highest hand, you win the pot and every individual who lost has to replace the pot. So if I win a $100 hand, you kick in $100 and the next hand starts off being worth $100, unless four people lost and then it’s $400. You can see that the amount of each hand could grow exponentially. That night, we vacillated from hands worth $500 to $4,000. There was one $10,000 hand but that’s a different story.

So, yeah, I made some mistakes. Because I had no idea what I was doing. After an hour of playing, I was down thousands of dollars. I had lost $1,000 and borrowed a couple thousand from someone else at the table, and I lost most of that, too. Inside, I was screaming at myself. What is wrong with you, you degenerate gambler moron? What did you think was going to happen? Meanwhile, I was getting good stuff. I noticed that Jay-Z stayed calm the whole night. Not just because he’s rich but because that’s how he is. He’s got ice in his veins no matter what’s going down. And he was really good at avoiding danger because he was great at reading people. He knew their tendencies, he picked up on their ticks. He was a great student of people. I don’t know if I would’ve figured that out if I had not been sweating out the game alongside him.

There was also a hand where Jay and I went head to head. I had a good hand. I thought I had him. I said, “If I beat you, I’m gonna put it in the story.” At that point in his career, his whole thing was “I will not lose ever.” He said that all the time in his music. He said back to me, “Yeah, but if you lose are you gonna put it in the story?” I said for sure. Anyway, I lost. He beat me. And I put it in the story. It was a rough hour.

Then, suddenly, around 1 a.m., the poker gods decided to show me some love. I was dealt two aces. I won the hand and a few thousand dollars. Then about 20 minutes later, I was dealt two kings. I won thousands more. By 2 a.m., instead of being down thousands, I was up $5,000. An hour later, at 4 a.m., Jay ended the game, and I walked out with over $4,000. I went out and bought an expensive new watch that I still have to this day. Jay-Z went on that night to make an even bigger bet — one hand for $10,000. For the story of that and the complete story of my crazy night gambling with Jay-Z, check out “Jay-Z Got Guts” in “Star Stories With Toure.”

Touré, theGrio.com

Touré is a host and Creative Director at theGrio. He is the host of the docuseries podcast “Being Black: The ’80s.” He is also the host of the podcast “Toure Show” and the podcast docuseries “Who Was Prince?” He is the author of eight books including the Prince biography Nothing Compares 2 U and the ebook The Ivy League Counterfeiter.

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