Molly's Game

by Molly Bloom

  Glen finally appeared at nine o’clock on a Friday night when I was doing an experimental game with smaller stakes, with a buy-in of only $5,000.

  I had all the girls working, dressed to the nines and drinking to loosen up the mood. I was hoping that by lowering the stakes and creating a party atmosphere, I could build a fun game that felt less serious than the big game. Eugene had brought along some of the biggest fish he had met and I filled the table with the rest of my recruits.

  Glen took one look at me when he walked in, and in his Long Island accent with all of the aggression and fervor of a trader, exclaimed, “What the fuck are you doing running poker games? You should be barefoot and pregnant, doing yoga or shopping.”

  His comment surprised me, but so did my reaction. I was offended, but my stomach also did a little somersault. It was the first time in a while that a man had spoken to me like I was a woman. He wasn’t exactly good-looking, but there was something about him that was attractive, while also simultaneously offensive.

  Out of the corner of my eye I saw Eugene watching us.

  Glen ordered a Red Bull and vodka, downed it in two seconds, and told Tiffany to keep them coming. Then he handed her a hundred-dollar chip.

  He was exactly who I wanted him to be.

  At the beginning of the night the game was exactly as I had hoped—friendly and social. But after Glen had a couple cocktails he started driving the action up. Soon he was in for $100,000 and the rest of the guys smelled blood in the water, and that was the end of my friendly game.

  THERE’S SOMETHING THAT HAPPENS to people when they see the opportunity to make money. Greed flavored with desperation, especially at a poker table, gives rise to a moment when the eyes change, the humanity vanishes, and the players become bloodthirsty, flat-eyed predators.

  The first time I really saw this play out was in L.A. when Ned Berkley, the bad-boy heir to his family’s company, came to play. It was very obvious that Ned didn’t exactly know the rules of poker. The guys sensed it immediately, flipped into greed mode, and turned into a hungry pack, and by the end of the night, Ned had lost a small fortune.

  The pack wasn’t done with him, though. They were drunk with greed. They asked Ned what he liked to play.

  “Blackjack,” he said, not wanting to disappoint his new celebrity friends. Not surprisingly, he was also a terrible blackjack player. The guys took turns playing the house. I could see them dealing cards as fast as they could. Nodding and whispering to each other.

  Their greed was so transparent that I cringed as I watched Ned’s face register what was going on. He tried to quit but they egged him on. He continued to play, lost graciously, and paid, but I knew he would never come back.

  GLEN APPROACHED, holding another Red Bull and vodka and wanting another $100,000.

  “Come talk to me first.”

  We walked into my bedroom, where he made himself comfortable on my bed.

  “Nice room,” he said, waving his arm at the floor-to-ceiling windows.

  “Thanks. So, I usually ask first-time players to post. I’m on the hook for the cash, as you know. Where’s your head?”

  I was only a little worried. Number one, my friend had vouched for this guy; number two, his ego was clearly life-size and his peers were at the table. Three, I had word from Vegas that he had won a million last month.

  But . . . he was drunk and getting killed.

  “I’m good for it. You have nothing to worry about.” Then he said, “Tell me about you . . . I’m fascinated.”

  I smiled but didn’t respond.

  “Okay, well. If you won’t tell me, then I guess I’ll go back to the table.”

  We looked at each other, and there was undeniable chemistry.

  I got up and walked out, and I could feel him close behind. Eugene stared intently at us as we walked out of my room. I smiled reassuringly at him.

  It was 3 A.M. and some of the more responsible guys were getting up.

  Keith Finkle, one of the hedge-fund guys from my big game proposed they play stud. Glen enthusiastically agreed.

  Oh no, I thought. This was bad. Hold’em was one thing, but stud was a bigger game with much more risk, and Keith was by far the best player I had ever seen.

  Meanwhile, I was getting calls from players from my other games—Illya, Eugene’s brother, and Helly Nahmad, both wanting to confirm that Glen was on tilt and bleeding money. I confirmed.

  Helly and Illya had been coming around more often lately, even to my smaller games. I heard they had put together a sports betting group that allegedly included John Hanson, the brilliant chess master, a kid from MIT who had developed an algorithm for picking winning teams, and an IT programmer-type genius to keep track of it all.

  They both showed up and bought in for a hundred grand, and Keith added chips as well.

  Suddenly my little $5,000 Texas Hold’em game had become a $100,000 buy-in stud game.

  As the sun came up, the girls and I scurried around dropping the blackout blinds and ordering breakfast and coffee for everyone . . . except Glen, who was on his thousandth Red Bull with vodka.

  My staff and I were exhausted but the game was crazy good and all the girls were cleaning up in tips. Glen was in for $400,000, so we ordered lunch, more cigarettes, and more vodka. We put on the sports channels for the guys: I had several television screens in my living room for this very purpose. But I was close to cutting Glen off because I couldn’t afford a hit this big if he decided not to pay.

  Most game runners are essentially running Ponzi schemes. They extend massive credit without actually having the capital to back it up: that’s why most games die. I didn’t work this way—I didn’t extend credit I couldn’t back up, and I always covered. I couldn’t afford to die.

  Luckily, Glen started winning somehow. He smiled and winked at me, and again, his flirtation affected me. There was something about his recklessness that was a turn-on. I looked at Eugene, and though I still loved him, I knew the limitations. He could never be a real boyfriend if I ever left this world.

  GLEN AND KEITH WERE IN A HUGE HAND, and when it went Glen’s way, it was a huge win for him. Keith bought $300,000. Glen was counting his chips.

  “Can I take three hundred K in chips off the table?” he asked. I looked at Keith. It was essentially up to the table to allow a player to put some of his winnings aside this way, because the rules said no. In a no-limit game, all money stays in play.

  I motioned to Keith to indicate that the decision was his to make, and predictably, he refused, so they kept playing. It was now 4 P.M. They had been playing for nearly a full day. I sent the girls home and brought in a new shift of dealers. Glen then lost a monster hand to Illya. Soon, maybe the exhaustion or the Red Bull caught up with him and he went on major tilt, and wiped out his whole stack.

  I watched him buy in for $50,000. When a losing player starts buying small in a big game, it usually means they will continue to lose.

  He lost it and stood up.

  “I’m done.”

  He went to use the bathroom. The guys surrounded me instantly.

  “Is he good for it?”

  “Will he come back?”

  “Can I get paid first?”

  I was exhausted and annoyed.

  Glen came back and motioned for me to speak in private with him.

  “Hey,” he said. “I have three hundred and fifty K in cash at my house. I won it in Vegas last month.”

  I nodded, feigning surprise.

  “I can get it to you now or tomorrow,” he said.

  “Now is great,” I said.

  As I was getting ready to leave, Eugene grabbed my arm.

  “You okay? Want me to come?”

  “I’m good, see you in a few,” I said

  This was another of my rules: You don’t ever let a gambler sleep on a debt if you can help it. You don’t want them to have time to lose it, or think too much about it and decide to stiff.

  Helly valiantly offered his white Pha
ntom and driver for my collections mission, and Glen and I enjoyed an awkward ride together in the back of the ostentatious car. We were both exhausted and he was nursing a wounded ego. But there was still an undeniable sexual tension between us.

  We rode up the elevator in a strange silence. He went back to get the money from the safe and handed it to me in an envelope. I stuck it in my purse.

  “Thanks,” I said.

  “I’ll call you tomorrow,” said Glen, and reached out to hug me.

  Startled, I tipped off balance and he caught me, holding me for a moment longer than he needed to before he settled me back on my feet. I was staring straight into his eyes and I felt like he was going to kiss me.

  “You must be exhausted,” I said, and the moment passed.

  “Yeah,” he said, but he was still staring at me intensely.

  “Good night,” I said. The sun was out and it was the middle of the afternoon.

  “’Night,” he said.

  I counted the bills on the way back to the apartment, and it was all there.

  When I walked in, the vultures were waiting.

  “Did you get it?”

  “Do you have it?”

  “Yeah,” I said. “We’ll deal with it in the morning. I have some things to figure out.”

  “Can I just get a hundred K?” asked Helly.

  “I’ll call you tomorrow,” I said, and went into my room.

  There was a knock on the door. I opened it and Helly was standing there with a look on his face.

  “Can I just have ten K? I owe my bookie.”

  I sighed and handed him the money, then shut the door firmly and lay down to get some rest. Eugene came in a few moments later and curled up next to me. For the first time in a long time we were on the same sleep schedule and I remembered how nice it was to not be alone.

  I WOKE UP TO A MESSAGE from Glen that said: I’m contesting the other 150. You should have let me take 300K off the table.

  I groaned and buried my face in the pillow.

  The game needed to be paid out, and I had guaranteed it. If someone didn’t pay, I would have to write the check. I knew Glen didn’t have a strong argument—or any argument at all—but in this world that didn’t matter. There weren’t any courts, judges, contracts, or police officers.

  Most game runners, when they got stiffed, behaved like gangsters; they sold the debts on the streets or hired muscle and tried to intimidate people into paying—or worse. That just wasn’t an option for me: I may have been operating in the gray but I still had a moral system and awareness (or so I thought) of the law, and intimidation and violence crossed both lines. My only line of defense was my understanding of human behavior and my problem-solving skills. I knew there was a solution; I just had to be smart enough to get there.

  After observing Glen for more than twenty-four hours, what I knew about him was the following: he had a huge ego, he was affected by pretty girls and seemed to want to impress them, he had a ton of gamble in him, he was an alpha male, and he had the money to pay. Based on the information at hand, I knew I couldn’t push him, and I couldn’t be threatening or appear angry. I just needed to provide compelling upside for him to pay his debt.

  The two most valuable assets in this debt collection were incentive, specifically access to beautiful girls, great games, and important people, and my femininity. If I could get him to view me as a woman whom he could save by simply paying his debt, I had a much better chance of collecting.

  I picked up the phone and called him. He answered gruffly, already preparing for a collection call in which he would stand his ground and maintain his position that the floor call had been unfair.

  “Hiiii, whatcha up to tonight?” I asked lightly.

  “Nothing,” he said, still stiff.

  “Come to dinner and the club with the girls and me.”

  He paused. I needed him to say yes. Getting “social” with him was a hugely important part of my plan.

  “Who’s coming?”

  I listed their names.

  “Okay,” he said. “What time?”

  GLEN WAS PROMPT, and visibly pleased to be the only guy surrounded by seven girls who were doting on him and laughing at his jokes. Not a word was mentioned about his debt that night.

  When the bill came, he made a big, ceremonious show of picking up the tab. I smiled and thanked him profusely. Inside I was laughing. He still owed me $150,000, so his attempt at chivalry fell about $149,000 short.

  We went on to a club, where the promoter gave us our usual welcome and escorted us to one of the best tables. The alcohol flowed, the girls danced, Glen kept looking happy. He came to sit next to me on the banquette. I was doing figures (the math of debts and collections) on my phone.

  “Hi,” he said. “How come you’re sitting here by yourself and not having fun like everyone else?”

  I gave him a brave smile.

  “I’m just a little stressed, trying to solve some problems.”

  “You’re too pretty to have problems.”

  “I came here after losing everything in L.A. and I really need this to work. I have mouths to feed,” I said motioning to the girls, “and something to prove.”

  “I get it,” he said, looking into my eyes. “We’ll figure it out. Now come have fun. It’ll be okay, I promise.”

  Bingo.

  Two weeks later, Glen showed up to my big game with a check for the $150,000. That night he won $300,000, so I ripped the check.

  He quickly became one of my most valuable players.

  I rarely saw Eugene anymore. He played in the day games, the night games. He was gone for days—he would come home and crawl into bed and sleep for twenty-four hours and then leave again. He wasn’t recruiting much anymore, and although he didn’t do it intentionally, he was supporting my competitors.

  Chapter 28

  I decided to get a house in the Hamptons for the summer. It was too hot in the city, and most of the players were out on the island for the summer anyway, so I hired a real-estate agent and found a sprawling mansion with impeccable grounds, an infinity pool, and a tennis court that came with a tennis instructor for the summer. The house was so big that the girls and I had our own wing. Strategically, I had arranged to share the house with Illya and Keith. This would almost certainly ensure plenty of games and gambling at the house, and I could offset the pricey rent.

  ON FRIDAY, the girls and I piled into my Bentley and headed east for the first weekend of the summer. We had a full social schedule planned—fashion shows, a new restaurant opening, and, of course, the annual Bridgehampton Polo Match, the official kickoff of the summer social season. We arrived in the late afternoon and the girls squealed with excitement when they saw the sprawling estate. Everyone raced upstairs to claim rooms and start getting ready.

  I made myself comfortable out by the large saltwater pool, dressed in a white dress, and began drinking rosé.

  The heaviness of my life had lifted and for the moment I had peace. My heart had that full feeling that only comes when everything in the world is right again.

  The Bridgehampton Polo Match was only attended by the who’s who of high society. Impeccably dressed socialites holding flutes of champagne in manicured hands, distinguished-looking gentlemen reeking of old money, A-list celebrities, and impossibly beautiful models congregated under the white tents, while handsome equestrians like Nacho Figueras warmed up on the lush green fields. It was easy to get lost in the novelty and glamour of it all, but I was there for a purpose. I knew this would be fertile ground for recruiting players. The girls and I found a table and sipped our champagne while taking in the scene. We were new faces on the circuit and it didn’t take long for a steady stream of men to approach the table. By now we were pros at subtly but quickly determining whether or not a guy was a potential player.

  I was entertaining a pharmaceutical-company billionaire when I looked up and saw Glen with his arm around a pretty blonde. To my utter annoyance I felt a pang of jealousy
. Eugene was my soul mate and I loved him in a way I hadn’t known I was capable of, but he was disappearing more each day. Glen was arrogant and self-absorbed. He looked over and we made eye contact, I smiled and quickly looked away. It was just as well. Nothing, absolutely nothing, good could come of dating Glen Reynolds.

  That night, we had a party at our house, and I continued what I had started at the polo event, working the crowd looking for assets/players. By the time I crawled into bed, I was exhausted but thrilled by the amount of contacts we had obtained.

  I wanted to call Eugene and tell him how well things were going, so I dialed his number. It went straight to voice mail, as usual. I thought about him dressed in black, going from game to game, not sleeping for days, and finally crashing in his gilded apartment in Trump Tower, alone. It made my heart hurt. And then I checked one last time to see if the awful Glen Reynolds had texted. He hadn’t.

  When Glen called me a few days later to ask me to dinner, I politely declined. But he wasn’t one to give up. He asked again and again, and I always said no.

  AND THEN HE GOT SMART; Glen knew the way to my heart was through my game.

  A week or two later, he sent me a text asking if I would do a game at his house in the city, saying that his Wall Street buddies wanted to play.

  I couldn’t say no. Glen had offered to bring new players. I showed up at his place with the girls, my dealers, my table, Shuffle Master, chairs, snacks, and an intention to be all business.

  “Sweetheart . . .” he said when he opened the front door, giving me his most charming smile. He folded me in a very tight hug. I patted his shoulder politely and wiggled out of his embrace.

  “Where should we set up?” I asked, trying to stay focused.

  He led me into his living room. His apartment was nice but it was definitely a bachelor’s pad. As his friends showed up, he introduced me. They were all young, rich, fast-talking Wall Street guys.

  It didn’t take long for the game to get crazy. The energy was great; these guys gambled in the market all day and seemed to ride out the swings easily. I started getting calls from players asking for seats.