Star Stories

Jay-Z Almost Bankrupted Me

Episode 1

Touré played poker with Jay-Z one night in a swanky Manhattan penthouse suite. Each hand was worth thousands of dollars. Why was Touré in the game? He’s not rich enough for a game like that. It could have bankrupted him. The answer: He’s insane. Also, he was willing to risk everything to glean the very interesting bit of psychological insight he could get from being head-to-head in a hand of poker with Jay-Z.


The Takeover

Writer: JAY-Z & Kanye West

Label: Roc-A-Fella Records

Publisher: Roc The World 

The Story of OJ 

Writer: JAY-Z, No I.D., Nina Simone, Gene Redd Jr. & Jimmy Crosby

Label: Roc Nation

Publisher: Carter Boys Music, Sony Music Entertainment, Virgin Records, EMI Longitude Music, New World Music, Warner Music Group, EMI Music Publishing Group, Filmtrax, Eleven East Music, Bucky Music, Rolls Royce Music Company, BMG, Let The Story Begin Publishing, EMI Waterford Music, BMG Monarch, Warner/Chappell, Delightful Music, Round Hill Music, Warner-Tamerlane Publishing Corp., Carbert Music & Stephanye Music

SAN FRANCISCO, CALIFORNIA – JUNE 02: Rapper, Jay-Z looks on during the second quarter in Game One of the 2022 NBA Finals between the Golden State Warriors and the Boston Celtics at Chase Center on June 02, 2022 in San Francisco, California. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Ezra Shaw/Getty Images)

Full transcript below.

ANNOUNCER [00:00:00] You are now listening to theGrio’s Black Podcast Network. Black Culture Amplified. 

TOURE [00:00:05] I’m Toure.  Star Stories is brought to you by theGrio Black Podcast Network, home of the Blackest Questions with Dr. Chrissy Greer and Dear Culture with Panama Jackson. This episode of Star Stories is about Jay-Z

TOURE [00:00:25] It started as a normal night. Just me and Jay-Z and eight friends playing poker in a penthouse suite at the Trump Tower. This was 2001, when Jay-Z was one of the hottest emcees in the game.  A very rich person. I was a writer who had been hanging around him for a week working on a cover story, and I would get paid about $4,000 for that story. So I was standing there watching Jay and his friends play poker and thinking, I know nothing about playing poker. And the guys in the game are rich, and the stakes for each hand are high. So, of course, the writer in me said, “Yo, it would be amazing for the story to be in the game with them.” To which the realist inside me said, “Wait, what? No, no, no, no, no. You know nothing about poker,” but I’m not one to let prudence get in the way of a bad decision. And that night, there would be a series of bad decisions. 

TOURE [00:01:16] Back when I was writing about rappers for magazines, the phone would ring, and sometimes they say, “Get on a plane and go interview Beyoncé or go hang out with DMX.” This is about the time I played poker with Jay-Z. It’s called “Jay-Z Got Guts, a.k.a. The Time I Almost Went Bankrupt Playing Poker with Hov.” So as I said, the night started off normal. I got to the suite around 9 p.m., and the poker game was already in full swing. This was a weekly poker game. I was told that mixed some music business whales and some big dogs from the street. There were several millionaires at the table. I had no business whatsoever getting in that game. But watching was not doing it for me. I was getting itchy. Then Jay leaned over to a cassette player and pressed play, and gave me a sneak peek at a new unreleased song he’d just finished. 

TAKEOVER Jay Z [00:02:11] R.O.C, you runnin’ this rap shit. 

TOURE [00:02:14] Hadn’t come out yet. The beat was hard as hell. And then he came in and savagely dissed Mobb Deep and Nas by name. 

TAKEOVER Jay Z [00:02:23] Ask Nas; he don’t want it with Hov. No. 

TOURE [00:02:26] Sounded like a declaration of war. I said, are you going to bleep out their names? He looked at me like, What? No. So I was listening to the Takeover, a song that would launch the Jay- Nas battle and change hip-hop history. And the first time I heard it, I knew he would have the impact of a nuclear bomb. He said I felt like I was being disrespected by them. So I had to show them. Okay. A few minutes after that, my impulse to get involved kicked in. I said, “Yo, let me get in the game.” What? Jay made a face like he was surprised and impressed and yet somehow scared for being. He said, “Okay,” like it’s your funeral. It was kind of like his okay in the story of O.J. I mean, he was, like, different, but like that one. It had layers. 

JAY Z [00:03:24] “Okay.”. 

TOURE [00:03:24] When I sat down at the table, I did not know what game they were playing. I did not know how much they were playing for. And I did not know much about playing poker. I was set to lose everything, but I’ll do anything for a good story. So let’s go. Jay explained the game was called Guts. They deal you two cards face down. That’s it. Based on your cards alone, you decide whether you want to stay in the hand or fold. If you stay in and you lose, you replace the entire pod. That could mean putting out several thousand dollars. As soon as I heard the rules, I said, Black Baby Jesus, what have I gotten into? But it was too late to turn back then. I took a deep breath, said a little prayer, picked up my cards. Now, Guts is all about poker faces, reading people, and having the cojones to risk thousands of dollars on a hunch. I do not have those qualities in abundance. Of course, Jay-Z does. He was then worth over $50 million in the stack of dollars in front of him that night was well over 30,000. I tried to count but lost track. The man was fearless, and he dominated the game. He rarely lost a hand when he went in. Every time that someone else got trapped, he avoided it. It was like he had an internal GPS that helped him navigate around trouble that was ahead of him in the game. I did not have that same sort of night at 10 p.m. I had $1,000 in front. At 11 p.m., I was down $2,000 like I owed someone else at the table, $2,000 that they’d loaned me so I could stay in after I busted out. Why was I still in? Even though I was the poorest person in the game, and I was in the negative for the story? It’s all about the story. But what if the story was great, and I went broke because of it? I mean, a few more bad hands and big loans, and I could end up owing someone a lot of money. I was teetering on the edge of real financial trouble, like not being able to pay my rent trouble. But I was getting good stuff for the story like this. Around midnight, there was a hand where Jay was the only person in the hand, and I was the last one to decide whether to stay in or drop out. The pot was $2,500, and I had a pair of nines. I felt good about that. Really good. Like, if he didn’t have a pair, then I’d beat him. And if he did have a pair, I beat him more than half of the time. Right? Really? There were only, like, five hands that could beat me. Did he have one of those hands? No. Going up against Jay was intimidating because he was scary good in this game. He seemed to be able to look into your soul and know whether or not he’d win. And I didn’t know what to do if I lost. But I wasn’t going to lose.  I had two nines.  I stared Jay in the eyes. He shot back an icy look. I said, “If I beat you, I’m going to put it in the story.” He said,  “But will you put it in the story if you lose? I said,  “Guts.”  That meant I was in. I flipped over my cards. Jay looked and said, “Hmm.”  I couldn’t tell what that meant had I won or not. Then he dropped his cards, and they fell in slow motion. And I watched as they slipped from his hand through the air down to the table. Now a word from our sponsors. 

ANNOUNCER [00:07:15] Thank you for listening to Star Stories with Toure. If you like the show, you’ll love the animated version of the series. Watch the adult cartoon series Star Stories with Toure at or theGrio Black Podcast Network’s YouTube channel. You’ll find the video links in the description section of this episode. 

TOURE [00:07:38] I flipped over my cards. Jay looked and said, “Hmm.” I couldn’t tell what that meant had I won or not. Then he dropped his cards, and they fell in slow motion, and I watched as they slipped from his hand through the air down to the table. They were two jacks. I had lost again.  Oh, my God! As I watched Jay scoop up the bills, a voice inside me began yelling at me. “What the hell is wrong with you? How could you be so stupid to get in this game and lose all this money? Now you are paying to do the story.  I can’t with you.”  I was so mad at myself. I was down $4,500. As I said before, my fee to do the story was $4,000. I was now losing money on the whole deal. What did I do? I borrowed some more. One last time, please. I’ll get you back tomorrow, I promise. Even though I probably didn’t have enough to cover it in my account. But I wasn’t lying to him as much as I was lying to myself. Was I a degenerate gambler who was crashing down to rock bottom right in front of Jay-Z. At that point, I couldn’t say no. I was so tired and so stressed. I thought I was about to have a heart attack. The time was then about half past midnight, and internally I was freaking out. But then, a few moments later, a bit of magic happened. I was dealt two aces on a big pot. I was way too happy when I saw my card, so I scared everyone out of the pot. But I still won and chopped off most of my debt. Suddenly I could breathe again. My shoulders loosened. I could feel my toes again. Fifteen minutes later, it happened again. Big pot in the middle. Two kings in my hand. This time I kept my poker face on. Let some people come in the hand. And I won that, too. And in about an hour, I had gone from being down 4500 to $5,000 up. And outwardly, I was quiet, but inwardly I was jumping around and screaming like, Yes. I knew I could do it. I’m the man I knew I had the cojones. I had the spark. I’d like to thank me for being me. But now it’s like 2 a.m., and we’re still playing. And I’m looking at the clock like, come on, hurry up. I don’t want to lose my stack. Let the game end. And then a song popped into my head, a Kenny Rogers song that my mom had loved when I was a kid. And the chorus, Kenny said,

THE GAMBLER Kenny Rogers [00:10:22] You never count your money when you sittin’ at the table. There’ll be time enough for countin’ when the dealing’s done. 

TOURE [00:10:33] Yeah, that’s true. Had to sit tight and be cool and not think so much about what I had. Had to relax. So I sat there. Played conservatively. Try to be cool as the clock wound down.  At 5 a.m., the game ended, and I still had $4,000 and a very happy inner voice. But, of course, the night had to end with a bang. Jay-Z loves competition, adrenaline, battling, and being the center of attention. So it made perfect sense that when the game started to break up, the president of Def Jam at the time, Big Kevin Liles, challenged Jay to a single hand of guts. Head to head for $10,000. Jay accepted. Someone shouted out, “Do it for a million.” Jay said, “No.” He said, “10,000 ain’t gonna make me sick. A million will make me sick.”  Everyone crowded around the table. Jay’s first card was Queen. Kevin’s first card was two. Jay’s next card was a king. Jay let out a little yell. He was ahead, but it all came down to the last card. The tension was palpable. The room was about to explode. Kevin flipped over his card—a three. Jay won. The room went wild; a table got flipped over. People were whooping and yelling. Jay stood at a chair, pointing at the sky like he just sank a game-winning three-pointer, smack-five with everyone in the room hard up to break their hands. And he yelled, “I bodied him.”  He started out with a stack of money in his hand so large he could barely hold it. Standing by the elevators, he said, “We introduced Will Smith and his crew to this game out in Aspen. I heard they can’t stop playing.” This game will claim your life. Trust me. I know. Almost wrecked mine. 

TOURE [00:12:30] Star Stories is brought to you by theGrio Black Podcast Network, home of theGrio Daily with Michael Harriot and Writing Black with Maiysha Kail. If you like this Star Stories episode, listen to the one about Snoop Dogg. Remember to rate and review. It matters. I’m Toure.