Molly's Game

by Molly Bloom

  DIEGO MET ME AT THE HOTEL with the table. The bellman had rearranged the room according to my instructions.

  Diego and I shared a special bond now. We were full-fledged partners in this strange and wonderful world.

  I chose my outfit carefully that night: a black dress that was just clingy enough to be sexy but not enough to be vulgar. Black Louboutins, Chanel pearls, and a light jacket, which was important because I liked to keep the game room cool. Colder temperatures keep players awake, and there was nothing worse than a tableful of tired, lethargic poker players. I wanted the table exploding with action, energy, and conversation.

  The chemistry at a table is so important. You must start with a carefully balanced mix of personalities. If the balance is off and the stakes are too big for some of the players, it kills the game. Too small, and everybody gets bored. The $50,000 buy-in had attracted these guys and so I knew they could handle it; I also knew that it would create pots big enough to make even the richest guys sweat a little.

  I reapplied my lipstick and I waited. I had invited the new friends I had made in Vegas, the “playmates” Tiffany and Lauren. The two of them showed up to serve drinks and to serve as decoration. They looked breathtaking. I knew the guys in the room tonight would have a lot that made them want to stay—on and off the table.

  The first player to arrive was Derek Frost, thankfully in regular clothes.

  “Nice setup,” he said, looking around the room and landing his gaze on Tiffany and Lauren. The two girls and I sat and chatted with Derek while we waited for the rest of the players to show. Tiffany was a real pro. She gazed at him with her turquoise-blue eyes, acted as if she were hanging on every word he uttered, laughed at his jokes, and made him feel like he was the one and only man in the world. It was impressive. And effective.

  Maybe because he was so disarmed by Tiffany, or maybe because it was what everyone who doesn’t have access says, Derek Frost, the guy who had bent my ear for an hour about how much he hated Hollywood and the scene, sure looked excited when Tobey showed up with Houston. I introduced them, and Tobey played his part of charming, funny movie star perfectly.

  Baxter showed next. He was a very successful trader who seemed a little ditzy but was a genius with numbers. I’d heard he’d been banned from several casinos in his younger years for card counting and was an absolute animal at the table, as I found most traders were. He always had the same routine of arriving and emptying out his pockets, which always contained a shocking amount of items: golf tees, pens, receipts, lip balm. He handed me his blank, signed check and I clipped it to my board. Every player that night had done the same—given me a signed check, with the amount left blank to cover their buy-in, and their losses if things didn’t go their way. For the moment the holding company of Molly Bloom Inc. was officially rich.

  Baxter went to join the other guys and I motioned Derek over.

  He picked up his backpack and followed me into the bedroom, opening the bag as soon as I shut the door. He knew what I wanted: he had $250,000 in cash and another $500,000 in Bellagio chips. As I explained to him at the coffee shop, I couldn’t extend him credit, so by bringing $750,000 he would be able to buy in fifteen times that night.

  Even though I was tripping on the amount of money I was being given, I smiled as if I did this every day. I didn’t want Derek to start to wonder about the fact that he had just handed three-quarters of a million dollars to a virtual stranger. “Great, I’ll just put it in the safe for now.”

  “Don’t run off with it,” he said.

  “I won’t, Officer Frost,” I returned, winking.

  We rejoined the others just in time to see Bosko and Gabe Kaplan walk in. They gave me a cool hello; they were old school and I knew it would take some time before they would show me any respect. I didn’t care. My game spoke for itself.

  Bob showed up next, and Baxter asked me if we could begin.

  “Guys, do you want to start?” I asked, above the excited banter.

  Of course they did.

  THEY DREW FOR SEATS, and the game was off and running.

  In the very first hand, Bob, Bosko, Baxter, and Derek were all in. I got the chips and the buy-in board ready. That hand went to Bob, which made both Bob and Diego, whom Bob punished when he lost, very happy.

  The guys reloaded, laughing and joking.

  “I’ll take two hundred,” said Baxter.

  I looked around the room for objections. Baxter wanted to make sure he had enough chips to take Bob down.

  “Actually,” Baxter said, “make it five hundred.”

  I looked at him and he nodded, so I counted $500,000 in chips, and gave them to him.

  “I’ll take five hundred too,” said Derek.

  I looked at Tobey at the same moment as he looked at me, and nodded to indicate that I had the money in cash. His eyebrows flew up and he looked impressed.

  I counted out Derek’s chips.

  “Give me three hundred more,” Bob said.

  Talk about a testosterone contest, I thought, counting out the chips. The cards hadn’t even been dealt for the second hand. As I counted the chips I looked around the table to see if anyone else wanted to play Richest Guy at the Poker Table. With no takers, the action continued.

  Eventually, Bosko and Gabe got up and went outside to smoke a cigar.

  I was in the kitchen filling drink orders. I could hear the men’s voices echoing from the patio.

  “Who the hell is running this game?” Gabe asked. He sounded concerned. He had a lot of money on the table.

  “The girl,” said Bosko.

  “The girl? What does she know? Who handles the money? Who extends credit? How do we know that Derek guy is good for it?”

  “We need to have this conversation with Tobey,” said Bosko. “We can’t trust that girl to do this.”

  My balloon of happiness deflated. I wanted to stomp out there and tell them both that I was smart and capable and I was managing the details of this game to a degree that would make their HEADS SPIN.

  But I didn’t. I couldn’t let them know they had gotten to me. This was no place for hurt feelings. I didn’t need these guys to like me, but I needed them to trust that I knew what I was doing. I texted Tobey and asked him to go calm their nerves and get them back to the table.

  Just then I got a text from Ben.

  Here, it said.

  A surge of excitement coursed through my body—and in that moment I realized how much I had changed. Back when I was a normal girl, the butterflies I’d be feeling at a moment like this would be because I was about to meet one of the most handsome, influential stars in the world. Ben Affleck showing up for my poker game was undeniably monumental, but the butterflies I was feeling now were excitement that he was playing at my table, that he was a part of my game.

  I GREETED BEN AT THE DOOR. He was tall and handsome, with a relaxed charisma that not all icons have in person.

  He looked surprised when I told him who I was.

  “You’re so young,” he said.

  “Not that young.” I winked. I was twenty-seven but I looked even younger.

  I took his coat and showed him the buy-in sheet.

  His eyes flew open and he looked at his watch.

  “Two million on the table already?”

  “Yep,” I said.

  “Okay, give me fifty K.”

  By now I had learned something about the psychology behind the way a guy asks for chips. Wanting to be overstocked or short-stacked at a table is a clear indication of playing style and ego. Whereas some guys want the tallest piles they can manage, the better to bully the table and scare people, Ben’s buy-in choice told me that he was a smart player who liked to limit his downside, especially at a table with a bunch of guys he wasn’t used to playing with.

  Rick Salomon showed up next. Rick was hot. He was crass and dirty, but he was still hot in a caveman kind of way.

  I pulled him aside to show him the board.

  “Wow, they are s
wingin’, huh?” he said, looking down at me. “Wanna fuck?”

  I looked back at him, praying my face wasn’t as red as it felt.

  “No thanks,” I said, as casually as if he had asked me if I wanted a Tic Tac.

  He laughed.

  “Give me two hundred K.”

  Holy shit. I had a HUMONGOUS poker game.

  As Rick took a seat, I saw him focus on Ben. I saw the wheels turning. Oh God, I thought, don’t let him say anything embarrassing. Rick had no filter.

  “Hey, yo, did that Jennifer Lopez’s ass have cellulite on it, or was it nice?”

  The table went silent.

  Ben looked at Rick.

  “It was nice,” he said, and pushed into a huge pot.

  The table laughed and the ice was broken. These may have been larger-than-life characters playing with larger-than-life numbers, but at the end of the day, guys are guys—and strangers quickly became familiar friends at a poker table.

  After that uncomfortable moment, and after Tobey assured Bosko and Gabe that I in fact knew what I was doing, the game took on a life of its own. It was one of those perfect nights where the conversation was lively, the action was fast and furious, and each one of my usually impossible-to-please players had a look on his face that said that he would rather be there, at this table, than anywhere in the world. My tips that night reflected the enormous success of the game. I think I walked away with close to $50,000. After the last player had left and Diego and I had cleaned up, I sat on the patio watching the sun come up. I had discovered an incredible niche, and I had learned the formula to make it successful and keep it legal. As long as I didn’t take a rake, or a percentage of every pot, I wasn’t breaking any laws. I didn’t need to take a rake, as long as I kept the membership exclusive and limited to celebs, billionaires, and easy money, the players would pay through generous tipping in order to be invited back, to have admission into this exclusive club. I had found a loophole in the system; no one else was doing what I was doing. There were home games, raked games, and casino games; but no one had figured out how to create an environment so compelling and alluring and potentially lucrative that the tips the players left were actually an insurance policy that they would be invited back. I was paying taxes, I was playing by the rules, but I had made the rules work in my favor.

  Part Four

  COOLER

  Los Angeles, 2008–2009

  Cooler (noun)

  A case in which playing a strong hand that normally justifies the maximum bet is beaten by a still stronger hand.

  Chapter 20

  My games weren’t the only thing that was going well. My summer with Drew had been a fairy tale. His parents had bought a house on Carbon Beach, the most expensive stretch of sand in Malibu, known as “Billionaires’ Beach,” and inhabited by celebrities and tycoons. They had also purchased the house next door, which at some point they planned to tear down in order to enlarge their home, but for that summer they gave it to Drew. We spent the weekends at the charming, multimillion-dollar beach shack.

  The McCourts, despite their wealth and status, valued family time. Drew and I attended Sunday-night dinners and baseball games on a regular basis. I loved going to the Dodger games, and watching Drew’s parents, Jamie and Frank, realize a lifelong dream of owning a sports team was both inspiring and romantic. We also spent a couple weeks in July at their Cape Cod summer home, and visited the Boston home where Drew had grown up. I wanted that summer to last forever, but it was quickly coming to a close.

  It was the last weekend in August and Drew and I were enjoying a late-afternoon stroll along the beach. Lucy ran ahead barking at the waves and rolling in every disgusting smell she could find.

  “What are we going to do for your birthday?” I asked. Drew’s birthday was the second week in September.

  “We could go to New York,” he said. “Watch the finals of the U.S. Open, eat good food, and go to the Dodgers-Mets game.”

  I smiled. In my new world, summer vacation really never ended. It was always warm and sunny and there was always something new and exciting to plan.

  “We can fly with my parents on their plane.”

  I wondered if I would ever get used to my new reality. I didn’t want to. I always wanted to feel this excited, alive, this fortunate, this on fire. Halfway down the beach, hand in hand, we ran into Rick Salomon, who had rented a house on the beach for the summer, a stunning testament to the enormous profit porn could yield.

  Shannen Doherty was Rick’s ex-wife and Drew’s ex-girlfriend, so I cringed a little, expecting an awkward encounter between the men, but neither of them seemed to care.

  “Hey, you think we can get a poker game going tonight?” Rick asked.

  “Sure,” I said immediately.

  “You should play, McCourt,” Rick said.

  “Another time,” Drew said. I knew he would never do this, and that was one of the things I liked about him. He wasn’t flashy and he seemed to have a healthy respect for the value of a dollar despite his family’s wealth.

  “I’ll put out some feelers and call you in a few,” I said.

  As we walked back I turned to Drew.

  “You don’t care, right?”

  I knew we had plans, but Drew would understand. It was business.

  He said he didn’t, but I felt some tension. It was work, and I would never stand in the way of his ambitions. Still I had a nagging feeling that I should have run it by him before I made plans to spend the night at the poker table, instead of at home with him.

  I pulled the game together in an hour or so. There were many more spectators than usual that night, mostly girls in tiny bikinis. The rapper Nelly had somehow appeared. He was very polite, and his entourage sat quietly on the couches nearby. Since it was the last weekend of summer, there were many parties going on along the beach and various people wandered in. This wasn’t how I usually ran things, but it was Rick’s game. Just as I was giving Nelly another buy-in, Neils Kantor rushed in. He came from a very rich family that was well known for its important collections of modern art, and Neils possessed the exuberance of a child, but beneath the juvenile facade he had a shrewd business mind. He was motioning enthusiastically for me to come outside. I asked Diego to watch the game for me.

  Neils grabbed my arm dramatically.

  “You will thank me for this,” he said, his eyes twinkling and his voice animated as he practically pulled me down the stairs onto the wet sand.

  “I’ve known Brad for years, he runs a huge fund, and he does VERY WELL. Lots of people I know have invested millions with him. Brad is also a huge gambler. I ran into him on the beach and brought him to you.”

  Neils looked at me happily like a puppy that had retrieved a ball.

  He was still pulling me when he stopped in front of an attractive guy dressed in beach clothes.

  “This is Bradley Ruderman,” Neils announced proudly.

  Brad and I exchanged small talk and I invited him inside. Unfortunately I couldn’t use Neils’s endorsement as a guarantee. I didn’t want to ask Neils to vogue either. “Voguing” means guaranteeing a loss for someone—in this case it meant that if Brad lost, Neils would cover the amount if Brad couldn’t or didn’t pay. The only vogue I really trusted was that of someone who played in the game, and Neils had not. He had the best intentions, I was sure, but I was in a difficult, and somewhat awkward, spot. I explained this all to Brad, who was now watching the game with a look in his eyes I had come to recognize as true degeneracy.

  “I would love to let you play but I need you to post or get someone from the game to guarantee you.”

  “Would Arthur suffice?” he asked.

  Arthur looked up and quickly nodded. That’s all I needed. I set Brad up with chips.

  Brad was the worst poker player I had ever seen. It seemed as though it was his first time playing the game. He lost buy-in after buy-in, until almost everyone at the table was up and he was the financier. The players were looking at me in disbe
lief as the feeding frenzy ran its course. I texted Arthur throughout, verifying each buy-in and explaining the situation. Arthur seemed unfazed.

  He can afford it, he wrote.

  At the end of the night Brad was down high six figures on a $10,000 buy-in. Yet he seemed totally happy.

  “Do you mind, my house is a couple doors down. I’ll just grab a check,” he requested politely.

  “Of course not,” I said.

  He practically ran out the door. I was sure he wasn’t coming back, but ten minutes later he showed up with a check for the full amount.

  “Thanks so much!” he said, giving me a kiss on the cheek. “Do you think I could play in the next game?” he promptly asked hopefully.

  “Sure, I’ll call you,” I said, trying to hide my confusion.

  Something had to give. This just seemed too good to be true. There was no way the check would clear. But it did, instantly. And so began the era of Bad Brad.

  DREW, TRAVIS, AND I were still half drunk as we drove to the private airport to meet their parents. We had made an early celebration for Drew’s birthday and no night was mild with our friends. Popping gum in my mouth and keeping my sunglasses on, I focused on keeping my balance as I marched up the narrow steps to the sleek G-5. Drew and Travis were in far worse shape. Drew and I claimed the couch in the back, holding in our laughter. His two younger brothers were forced to sit in front with Jamie and Frank, their parents, who were, as usual, focused on business.

  I had been to New York City a few times—a summer camp excursion to the Statue of Liberty and Empire State Building, an overnight stay in Queens on the limited ski-team budget before heading to the Olympic Training Center in Lake Placid, and a layover on my way to Greece. I was excited to really see the city now. I grabbed a coffee in an attempt to sober up. I didn’t want to miss a second of this experience. We landed at the private airport in Teeterboro, New Jersey, where we were met with slick black SUVs. I stared out the window at the shooting verticality of midtown Manhattan. We pulled up to the Four Seasons, and uniformed doormen rushed to open the car doors, retrieve our bags, and lead us into the opulent lobby. It was as if being rich filtered out the inconveniences of life and left you with only the best parts.