Managing Partner at Dragonfly Capital. Effective Altruist. Airbnb, Earn.com (acquired by Coinbase) alum. Instructor @ Bradfield. Writer. Former poker pro. Donate 33% of my income to charity.
Lately, I’ve been thinking about the infamous “million dollar bet” I made back in 2011. Today, I thought I’d repost the original story on this blog so it’s all here in one place. I was originally planning to rewrite it, but I’ve decided instead that I should post the whole thing unedited. It was very raw when I wrote it, and that rawness comes through in the writing. It’s an intense story—just reading it takes me back.
I’m writing this sitting in my car at a rest stop somewhere in the panhandle of Florida. I am reclining in my chair trying to get comfortable, but I can’t. I have all my stuff packed into the trunk and back seat. Rain is pelting the windshield, casting speckled shadows on my hands. I’m tired but I can’t sleep. I don’t know what time it is. Maybe 11, maybe midnight. I haven’t been able to sleep well lately. The last few days have been tough.
I wasn’t sure how to write about this. I wasn’t sure what kind of a story there was to tell, or who really I would be writing a story for. Ultimately I just know that I need to express what I’m feeling and what I’ve gone through.
I suppose everything began last year. I took a long break from the game; I was away from poker for about 9 months after I got hacked. I was focusing on my own life—on getting healthy in both mind and body, and I was keeping my distance from the world of poker. I would attempt a few times to get my head back into the game, but it just wouldn’t stick. I just didn’t have that same drive to keep playing the game.
When I went to Vegas for the first time when I was 20 (July 2010), I met a lot of poker players I’d only known online, and one of those players was Jungleman. I found he and I had a lot of perspectives in common and he really admired me. We spent a lot of time hanging out and decided that we might live together at some point later in the year. We settled on going to San Diego around October, and we invited Ashton who we both knew to come live with us. He was going to school and wrestling at the time so he couldn’t leave Orlando, but he ended up offering us to both come down to Orlando and live with him. It seemed like a good idea, since all three of us were strong poker players and we were all young.
So we did. Jungleman and I came to Orlando. The three of us spent a lot of time together—playing poker, feeling out the city, being young and stupid. For me this experience was a great opportunity since it was a chance for me to get my head back into the game, to focus, study poker, and to learn from these two really great players. It helped to re-ignite my passion for the game and also get my poker game back on track. I was a lot more mature than the two of them. Both Ashton and Jungle respected me. They would call me the “papa bear” of the house. I looked after them.
It was an interesting relationship between the three of us. But, well, I suppose the real story starts a few days ago.
Doug, a.k.a. WCGRider, had come to spend a week with us in Orlando. Jungle was supposed to be back from Australia on the 4th, but he ended up getting delayed so he wouldn’t be back after Doug was gone. So it was just me, Ashton, and Doug.
Ashton had decided to buy some tickets to the Magic-Heat game on Thursday night. He offered me a ticket to the game, but I passed. I didn’t feel like going. He ended up taking Doug as well as some other friends.
It was rowdy, they did a lot of drinking, and after the game they went to House of Blues for a concert. Doug later recounted the story to me: he went up to the bar at House of Blues to buy some drinks. Ashton came up to him and said “Hey, don’t worry about it man, I’ll get the drinks, it’s fine.”
Doug said, “Nah , don’t worry about it. You already bought the tickets, I got the drinks man.”
Ashton replied “Well, thanks… …You know… I feel sad all the time.”
Doug looked at him.
“I feel anxious and depressed, and I haven’t been happy in a long time.” Doug listened with a seriousness amidst this concert at the House of Blues.
“Well man, if you want help, all of us are here and are willing to help you.”
He continued, “If you want to get your shit together, you need to stop all the prop-betting, you need to stop all the craziness, you need to just focus on poker, on school, and on your health man. And you can do it. We all know you can.”
Ashton smiled at him. “Yeah, you’re right. I can do it. I can change.” And then the night went on. Ashton ended up leaving with a girl around 3AM. Doug and Ashton’s sister who had also gone to the concert ended up driving back to the house by themselves.
Now, I was having trouble sleeping that night. I’m usually the first person awake, but I’d gotten up especially early that morning and ate breakfast. At about 11 I came into the living room and saw Doug sitting on the couch playing poker, and Ashton sitting at his computer. Ashton had only gotten home five or six hours ago, and had slept maybe four hours. He’d drunk quite a lot the previous night. He was on Skype with Justin Smith.
Doug and I watched as Ashton asked him to set up a prop bet with him. The very next morning, after four hours of sleep, Ashton was trying to set up a prop bet with Justin as to whether or not he could run 70 miles in a day. Justin was hesitant to accept—the more Justin hesitated, the higher Ashton raised the odds.
“No, no, no…” Justin replied.
“Okay, 3-1… 3.5-1, because you’re my friend.”
As this went on, Doug and I exchanged looks as if to say—is he really doing this? Ashton looked at me and said “Haseeb, 3-1 sounds fair right? You’d take this bet at 3-1?”
I looked at him incredulously, glanced at Doug, and replied “Uh yeah, 3-1 sounds fair.”
Ashton turned back to his PC and finally said, “alright man, I just really want to do this run… 5.5-1.”
Justin simply said, “I’m going to sleep” and hung up. Ashton was visibly frustrated.
He then turned to me and said “Alright, you’re booking that right?” And I said “Well dude, I’m not sure that’s such a great idea.”
“No man, I’m going to do this. I can do 70 miles no problem. I know my body.” We discussed it and asked what’s the most he’d ever run before. He told us that the most he’d ever run in one stretch was twenty-two miles. Ashton is very athletic; he’s a collegiate-level wrestler, he ran cross-country in high school, and he’d run 13 miles just a couple of days prior. He’s extremely fit. But he’d never even run a complete marathon in his life. He looked at me and said, “What’s the most you can do?” I considered this for a minute.
As I was looking at him I thought to myself…I’ve been in this situation before. I’ve seen Ashton make lots of silly prop bets. I’ve seen him get scammed, burned, taken advantage of countless times, and I’ve also seen him offer a lot of silly prop bets that weren’t in his favor. Every time I’ve refrained from taking part; refrained from having anything to do with it. I know that he fucks up a lot, and I know that he’s a degenerate sometimes. I’ve known Ashton for years and I’ve watched him travel down his road. Many times along the way I’ve tried to stop him, to advise him, to pull him out of harm’s way, but ultimately he finds himself there again and again.
I had come to realize that I can’t stop Ashton from doing these things. I knew that no matter what I said or did, he was determined to do this prop bet. I know him, I know the frustration and anxiety he’s been feeling, and I know the look in his eyes and the resolve in his voice. I thought there was no way that he could run 70 miles. The way I saw it, he was ready to grab a handful of his money and throw it into the wind. I can’t save him. I can’t stop him.
I replied, “Alright, I can do 70. 70k for your 210.”
“Alright, it’s booked,” he replied. He finished eating his Dunkin’ Donuts and ran upstairs to change into his shorts. It was around noon then. We set up the terms of the bet—he was given a span of 24 hours to complete the run. He had to maintain a running speed at all times on the treadmill—any walking or anything below that given speed would not count toward his total. He was free to take as many breaks as he needed. Doug up took a small piece as did another friend, but most of the action was mine.
He scurried off with a spring in his step to the nearby gym to start his running. And so at 12:30 PM on Friday the 4th of February, the bet began.
Doug and I began making phone calls. Anyone and everyone we knew who was knowledgeable about running, who had run marathons, who knew anyone who had run marathons. We asked people if they thought it was possible—some guy who’s a collegiate wrestler who used to run cross country in high school, who had never run a complete marathon in his life. The overwhelming consensus that I got was that his chance to win was low, and some pegged it at close to 0%. Everyone who I asked about it was skeptical, and once I told them that he wasn’t allowed to walk, I was told it would be close to impossible for somebody without any training in supermarathon running. To top it off… I hadn’t mentioned to anyone that he’d been drinking the previous night and had gotten four hours sleep, or that he was offering me 3-1 on the bet.
At that point I thought that if all these people think Ashton can’t do it, then there’s no way he can win. He thinks he knows his body, but you can’t know how your body would respond to that level of physical and psychological stress if you’ve never been there. He can’t know. He can’t know what three back-to-back marathons would do to his calves, to his knees, or to his heart. He still had alcohol in his system and had gotten almost no sleep, and I knew that he was feeling anxious. I figured this is Ashton standing in front of the railroad tracks again—this is him sitting at 500/1k heads up against Phil Ivey with his roll, desperate to have something change, for something to rile him up, to feel alive and meaningful again. He wanted to make himself the hero. The way I saw it, there was no way that Ashton could do this.
Doug and I went back and forth from the apartment complex gym where he was running. We brought him Gatorade, power bars, water bottles, and checked up on him to make sure he was alright and watched his progress. His sister decided to spend the day with us (after learning what he was doing), and helped us out ferrying food and drink back and forth. We watched him, kept track of time, and measured up his progress. At that point, it still seemed like just a frivolous spur-of-the-moment bet. I figured that my role was to make sure that Ashton was going to be okay once he got through to the other side—that after he gave up or lost the bet, that he’d be able to get his mind back together and get back on his feet. I knew it’d be hard on him when he lost.
Around 2PM Doug and I went to Ruby Tuesday’s to get lunch. While we were eating, we got a text from Ashton saying that he was looking for more action, and that he was going to find other people to buy it up so he could put up 900k of his own money. I remember when he read that text aloud to me, Doug looked at me dumbfounded. We had no idea how to take it. The first thought that came to our minds was that Ashton was self-destructing. That he was putting it all on the line, and wanted all-or-nothing. I remember thinking that the sweat-drenched Ashton, in that musky little gym probably felt happier and more alive running on that treadmill than he had in some time. He had meaning in that moment. He must’ve felt that every pound of his muscle, every strain of his body had a meaning and clear direction behind it. He knew exactly what he was fighting for, what he was hurting for.
So I texted him, “alright, I’ll buy up the rest.” He texted back, “Are you sure about this?” “Yeah, I’m sure. My 285k plus the other 15k you have booked makes 300k. Consider it booked.”
I thought to myself, he’s giving money away. He’s not going to stop until he sells off all of that action and puts up 900k of his own money. If I know he’s going to throw 600k into the wind, what difference would it make if it were my hand that caught it instead of somebody else’s? I mean, that’s what poker players do isn’t it? They make their plays where the money is. They don’t hold grudges. We’re just two poker players, playing a game. Whoever wins just made the right decision in that moment, and the loser understands that. It’s not personal. Poker isn’t personal. Well, it’s not supposed to be, anyway.
As we drove back to the apartment complex, Doug and I were reflecting on how bizarre and fucked up the whole situation was. This was the most money I’d ever put on anything like this—I’m not a prop bettor, and the most I’ve ever bet on something was less than $1,000. It just felt surreal. Just talking about it made it start to feel more and more incredible (in the literal sense of the word). Doug said to me “Well you have to admit, either way, Ashton is a fucking animal.”
I replied, “Well, that’s true, but we’re not betting on whether or not Ashton is an animal. We’re betting on whether he can run these 70 miles today.”
Once we returned, I caught up with Ashton on his way back to the gym and we spoke briefly. He asked me if I was sure I wanted to do this, and I told him I was. He said to me, “Why? Do you think that I can’t do this? Do you think I don’t know my body?”
I chose my words carefully. “I…I just think the odds are too good man. I can’t pass up this bet.”
He said, “Okay, then if you want to take this action there are two terms you have to agree to. The first is that you think there’s a 0% chance that I would cheat. That doesn’t mean you think there’s a 1% chance that I’d cheat and you’ll live with it, but you have to literally think there’s a 0% chance I’d cheat you.”
“Yeah, I know you’re not going to cheat. Don’t worry.”
He continued, “Alright. The second term is that… this doesn’t affect our friendship, even if I win. Or if I lose. We’re still friends.”
I studied him, thought for a moment and said, “Well, if you lose, are you still going to be friends with me?” “Yeah.” “Well, if I lose I’m not going to hate you. So it’s fine, we’ll still be friends.” I patted him on the back, and then we shook hands. Thinking back, it didn’t feel like a million dollar handshake. Actually, I’m not sure what that would feel like, haha. I suppose it still didn’t feel real. I just figured I’d regret it if instead of me some random poker player out there was 600k richer tomorrow. I kept making what I thought was the right move, but it would take me a while to process the gravity of what I had agreed to.
Ashton returned to the treadmill and started running again. It was 2PM then, and my anxiety was starting to build. I remember telling Doug, “You know, for 70k I could almost be zen about it. Losing 70k would suck, but I’d be alright. I could still focus on other things. But 285k man… the difference between winning and losing… -285k or +855k. This is a million dollar bet. I didn’t realize this, but I’m not going to be able to play poker today man. Hell, I’m not going to be able to think about anything else…” He told me, “of course, what did you expect? You’ve got one hell of a sweat ahead of you man.”
Time dragged by slowly. Doug and Ashton’s sister continually updated me on his progress every half-hour, and I passed the time calculating Ashton’s progress and mileage rate. I spent a lot of the time talking to friends and trying to keep myself grounded. I spoke to a friend of mine (who isn’t a poker player) about the bet and he asked me, “So what are you going to do when you win your 850k?” I said, “Well, I don’t know if I’m going to win yet. I could lose. But if I do win, I’m probably just going to buy a car and put the rest away.” He chuckled. “What, like a hundred thousand dollar car?” And I said, “Nah, probably more like a 30k car.” He knows me, and I’m not a flashy person when it comes to money—I live pretty simply, and I prefer it that way. He said to me, “Ah, man. Money is wasted on the rich.” I laughed.
Ashton returned to the house several times, complaining that he felt tired a lot sooner than he expected. Around 4PM he curled up on the couch and announced to us that he was going to sleep for a bit. He didn’t sleep, and ten minutes later he got up and went back out to run again. At 6PM he returned and announced that he was going to sleep for a few hours in his room. He stayed in his room for ten minutes, told us that he felt energized already, and then was out the door again. Ashton was completely unable to sleep. Doug and I figured that was definitive—he wouldn’t be able to win. Without rest, his body wouldn’t hold up.
At around 8PM, I spoke to a friend of mine who had some experience in running marathons. I told her the entire story, about how Ashton was feeling out of it, how he was unable to sleep, and that he’d been drinking heavily the night before. She told me with an unexpected graveness—”You guys need to be watching him constantly.” I replied, “Well, we’re checking up on him every half hour or so, bringing him food and drink and stuff.” “No, no, you guys need to be there in case something happens. If he collapses or gets a heart attack, he’ll need immediate medical attention. Somebody needs to be there. Like, right now. The likelihood will only go up the longer that kid runs.”
Slowly, the realization settled in. I know Ashton, and I know how much heart he has. He’s a beast. He’ll keep pushing and pushing until the brink of his physical limits. The question was never whether Ashton had the force of will to win this bet, but whether or not his body could withstand it. In reality, I knew that Ashton wouldn’t give up. The bet I was making was that Ashton would be physically incapable of going any further. I was betting that Ashton would either: pull a muscle and be unable to run, collapse from exhaustion, damage his joints, or have a heart attack. There was no other way that he would lose.
From that point, Doug and I agreed to watch him constantly, but before we could commit to a vigil Ashton had returned home around 9:30 PM. He said that he was going to sleep again, and this time he was in his room for a while. Doug and I waited around along with Ashton’s sister in the living room downstairs. It all felt uneasy. Ashton’s sister asked, “Do you guys think he’s sleeping?”
Doug told us that he’d seen Ashton earlier when he stepped in to use the bathroom. He said that Ashton was sitting on his bed, just rocking quietly back and forth. “There’s no way he’ll be able to sleep,” he said. “When I did my prop bet, I had to do something like that. It was different, but just like Ashton I had a time constraint and a lot of pressure. I remember I would play and play for hours during the day, and then when I realized I was tired I’d crawl into bed. But when I got into bed, I would stare up at the ceiling and all I could think about was the playing that I could be doing, and I would think about the fact that I wasn’t sleeping, and I would get scared that instead of lying here staring at the ceiling I could be playing more hands, and then I’d get up and go try to play again… and when I realized I was too sleepy, I’d go back to bed and try again. The sleep was the hardest part. It’s impossible to sleep when you’re scared and the adrenaline is rushing. Trust me, Ashton won’t be able to sleep.”
Ashton’s sister asked if there was anything she could do to help him sleep. He shook his head. The story seemed to be getting more and more fucked up the longer it went on. I wasn’t expecting any of this. Ashton was going through something truly horrible. Rocking back and forth in that bedroom… all the fear and confusion he must’ve been feeling… us sitting downstairs waiting for our friend to give in. He was falling behind pace to win the bet. I was supposed to be relieved, but I felt miserable. The entire thing started to feel perverse.
Around 10:30PM his sister told us that Ashton’s parents were on their way up here from Ft. Lauderdale, 3 hours away. Doug and I had no idea what to think. According to his sister, he had called his mother and simply told her “You need to come up here. I need your help.” His sister had tried to get them to turn around, but they were insistent on driving up. This whole affair started to feel more and more like it was spiraling out of control, and we were now going to have to explain to his parents the whole situation. Doug was taken aback, but I was prepared to tell his parents everything.
It was almost 11:00PM and Ashton was still in his bedroom. He had completed 30 miles of the 70. Midnight would be the halfway point in the bet, and it seemed that he still had not gotten a wink of sleep. At this point, I was positive that the bet was over. Ashton had simply underestimated his own exhaustion. He had not even reached half of the mileage—and the first marathon would be the easiest. There was no way he could run the second and third marathons at a faster pace. I thought my role would be to explain to his parents what all had happened and why. I thought it was over.
Half an hour later, his parents arrived and went straight upstairs to Ashton’s room. Doug and I sat in the living room wringing our hands, unsure of what was going to happen. We spoke to each other in quieted voices, almost rehearsing how we were going to explain it to them. Finally, we saw them descending the stairs and taking notice of us in the living room. His mother smiled at me warmly, offered her hand and said “Hi, I’m Julia.” I introduced myself, and she walked toward the kitchen to set down her purse. “I can’t believe what Ashton’s doing,” she said perhaps to herself, “I can’t believe how reckless he’s being… but most of all I can’t believe the people who are making Ashton do this.”
Doug and I looked at each other. She didn’t realize that we were the ones he was betting against. I stepped into the entranceway of the kitchen as she leaned back against a countertop, and announced to her, “well actually Julia. We’re some of the people who bet against Ashton. Not only us. We and several others.”
The moment she heard me say that, she broke eye contact and tightened her shoulders. Her demeanor changed entirely. She bit her lip as I started to tell the story, from the very beginning… not omitting any details… about how I knew her son, about our relationship, about how the bet began, about what had happened thus far… about how much money was at stake… about the risks he was taking…, and I remember telling her “Ultimately, Ashton called you two here for a reason. He wanted you two to see something. What that is, I can’t say, but all I know is that you two need to listen to what he’s trying to tell you.” I remember feeling confident in my words.
“You say you’re his friend Haseeb?” From then on, she didn’t speak to me… she spoke AT me. She didn’t look me in the eye again. “No, real friends wouldn’t put their friends health at risk to try to take his money. You knew exactly what it meant when you bet against Ashton. You’re not his friends.”
We protested. No, I said, he was going to do this anyway. I couldn’t stop him. He was going to do it anyway. I was helping him wasn’t I? I was worried about him wasn’t I? I was watching over him wasn’t I? What difference did it make whether it was my money or someone else’s?
“No Haseeb, you two aren’t his friends. It’s all about money isn’t it? That’s what you guys want right? That’s what you’re here for, that’s why you’re making my son do this?”
No, no. No…
“Right, well your actions say otherwise. Well, Ashton isn’t going to do this,” she said. “I’m not going to let risk my son’s health so that you two can get your payday. He’s not going to do this bet.”
Well… that’s not your call.
“No, it is my call. I said he’s not going to do this. There’s no amount of money that’s worth risking his health for, and if you were his friends you would know that. You two can find me and come to me personally and… I’ll figure out how to pay you. But this bet is over. You guys will get your money.”
Doug and I looked at each other. I didn’t know what to say. She looked at me like I was a complete piece of shit. The parents went back upstairs to check on Ashton again, leaving Doug and I standing in the kitchen. I walked to the living room and sank into the couch.
I knew that as his parents, they were bound to feel that way. There was no other perspective they could have, really… I could see why they would think that we were just scum. I had seen Ashton cheated, ripped off, taken advantage of by countless people before. It would make sense that not knowing the situation, she’d think of me as just another one of those people. Of course she would. But I couldn’t shake what they said. It stuck with me, and slowly gnawed at my mind. The memory feels raw. I still remember it.
I’ve arrived safely in Austin at my parents’ house. My car parked on the street and is still packed with all my stuff. It’s been a while since I’ve spent the night here. I’m sleeping in the guest room, since the bed in my old bedroom is too small for me now. There was a big storm here last night. I woke up a couple times in the middle of the night to hail pounding the roof and windows creaking. It’s still cloudy this morning, but the weather has calmed. I have forgotten how quiet this place can be.
Earlier today I read some of the comments on the first part of my blog. I wasn’t surprised at the assortment of awe, compassion, and indignation. But ultimately, this story isn’t about other people, and it’s not something I wrote to be gawked at or as a testimony for others to pass judgment upon, although I have no qualms if they do so. I have thought about these events a lot in the last few days that I’ve been driving on the road back to Austin. They say silence is fertilizer for the soul. When you’re alone only with your thoughts, all you can really think about is the things you’ve done, about where your life is going, and who you are.
I wrote this story because I think it’s an important story to tell, for myself and for others to learn from. Writing this isn’t about making myself feel better, or to try to justify anything that happened. It’s about owning who I am and how I feel about what happened that day. The rest, as they say, is history.
The parents had gone upstairs to check up on Ashton again, and Doug and I were slinked on the couch downstairs. At that point, we were only waiting. For what, we didn’t know. Ashton’s mother had declared to us that the bet was over, but we knew that Ashton wasn’t going to simply concede. We knew he was going to fight and insist that he could go on and pull it off. The time was almost 11:45, and he was still less than halfway through the distance. I thought the bet was over and we were going to deal with the aftermath. I remember sitting there on that couch and just feeling guilty and uncertain. We waited.
Finally around 12, Ashton’s sister (who had defended us to his parents) came downstairs. She told us they were trying to talk to him, but Ashton wasn’t saying much…all he said was he wanted pasta. She asked if either of us knew how to cook spaghetti. Doug and I looked at each other. “You do know we’re poker players right?” She shook her head at us, and we laughed.
I went into the kitchen with her and poked around getting a pot ready for boiling spaghetti, and she gave me instructions while she returned upstairs into Ashton’s room with the rest of her family. So I stood over the stove and watched the spaghetti. I remember asking Doug as I was standing over the stove, “Do you think I just came across to his parents as a total prick? I don’t understand it. I mean I look out for Ashton don’t I? I’m his friend aren’t I? They were talking to me like I’m a slimy piece of shit. He was going to do this anyway, I know I couldn’t stop him…I don’t have control over him. I can’t help someone who doesn’t want my help.”
He told me thoughtfully, “Well man…I think you’re right. And I think they’re right too. The answer probably lies somewhere in the middle, really. I don’t think you did anything wrong. I don’t think Ashton thinks you did anything wrong. And if I were his parents and I saw this whole mess, I’d probably react the same way.”
“I know man, I know. I would too if I were his parents. But I just can’t shake this feeling. I feel like shit about this whole thing.”
“Well, we’re in it now. We just gotta deal with it,” he told me. The spaghetti softened slowly, and sunk to the bottom of the pot.
Ashton finally came downstairs. He was wearing sweatpants and a black hoodie with the hood over his head. I asked him how he was doing, how his legs and knees felt. Fine, he said. We didn’t ask him about whether he was going to continue the bet. The way he walked in and was searching for food, we knew he was going to keep running. He didn’t seem unnerved… he just wanted pasta. It was almost scary how comfortable he seemed. His sister poured him a bowl of spaghetti, and he sat down at his computer desk to start eating.
As he ate, he pulled up some music on Youtube. It was a dubstep track. “Have you guys heard this song?” We told him we hadn’t. “Oh my god, it’s so good.” He started playing the music for us on the computer speakers as he ate. He bobbed his head to the beat, and soon started to air-drum on the desk. He ate his spaghetti that way, jamming to music he wanted to share with us. He still saw us as his friends, and in his silly way Ashton was still okay.
I remember looking at him carefully. I didn’t dare to take my eyes away. The occupied expression on his face as he was clicking around on his computer, slurping that spaghetti. The bold white lettering on the hood of his hoodie, “TO WRITE LOVE ON HER ARMS.” The silence that we didn’t dare interrupt, as though we were just waiting for him to speak again. A tired boy in a hood eating spaghetti at his desk. I remember thinking to myself very clearly: remember this sight, Haseeb. You will never forget this as long as you live. I said nothing. I just watched him. He ate slowly and unhurried.
When he finally finished eating, he talked to us some more as he sat there digesting. Joking and laughing…he barely even acknowledged the insanity of the situation he was in. I remember thinking, how can he be so energetic right now? He seems happy. Is he happy right now? I said very little.
At around 12:30, he went back upstairs. When he came down, he had changed into his shorts and marched out the door once again, his parents following quickly behind him. They hadn’t said another word to us after our previous exchange. In the end, I thought to myself, they couldn’t stop him either.
So the bet went on into the night.
Doug had been coming down with a cold all that day, and his cough was getting noticeably bad. I told him that he should get some sleep and drink lots of liquids. There was no point in him staying up if the parents are going to be watching Ashton all night. I’ll make sure everything’s all right, I told him. He agreed and went upstairs to get some much-needed sleep. I was sleepy too; I hadn’t gotten much sleep the previous night and my exhaustion was building, but I felt like I needed to stay awake.
Ashton’s sister and her boyfriend were in the living room with me. I told the sister, “I just wanted to tell you, I’m really grateful that you guys are here. I don’t know how we could’ve handled all this if you guys weren’t helping us out.” She smiled and said not to worry about it. She and her boyfriend just laughed and said it was typical for their family.
They weren’t phased at all. They were giggling at each other’s jokes and pulling up clips on Youtube… they seemed so comfortable in the midst of all of this madness, just living and making the most of things. I realized that I admired them. I remember telling Doug before he took his Nyquil and went to bed, “Man… thank god for normal people.” He grinned and agreed. “Fuck the poker world,” I said, “We need to learn to be more like them.” Doug went upstairs to sleep and the two of them ended up falling asleep together under a blanket on the couch.
At around 1:30AM, I realized I was so exhausted that I needed to get some sleep. I went to my bedroom and set my alarm for 2:45AM, deciding that I was going to get up and sweat Ashton for the rest of run. I was just too tired, I could barely keep my eyes open and my mind just felt racked with exhaustion. It all felt like too much. I remember staring blankly at the ceiling. I wanted to push my anxiety down and just sink into the covers. It took me a while to fall asleep.
I scrambled to my feet and checked my phone. It was almost 5AM; I had missed my alarm. I must’ve been too tired and slept through it. Fuck, fuck. I threw my clothes on, shoved my feet into my shoes, and ran out the door toward the gym. I realized I had to piss along the way, so I went into a corner behind some hedges and relieved myself. It made me feel surprisingly relaxed…I felt like I’d be ready to face the scene before me. I walked around the side of the building, entered in the passcode to the gym, and opened the door.
His mother was sitting on the recumbent bike, tinkering with a game on her phone. His stepdad was standing near Ashton, his arm resting on an adjacent treadmill. He was watching a cartoon on the TV’s that were suspended over the wall. Neither of them looked at me or even acknowledged my presence. I said nothing.
I walked over to the far side of the gym, and sat myself down on a weightlifting bench. I checked the time on my phone—it was 5:15 AM. I decided to myself I would stay the rest of the time and just watch him. I thought I would be able to.
I sat there blankly for some time as he was running, just feeling my brain slowly process everything. All I could hear was the mechanical whirr of the treadmill, and the pounding as his feet hit the tread. It was so perfect and continuous, like a metronome. I studied him carefully. He was stripped down only to his boxers. His skin seemed to be stretched taut over his musculature. His face was looking down and toward the left as he ran…his gait almost seemed like he was scurrying to catch up with the treadmill. His eyes were blank. I didn’t know what he was looking at or thinking about. I remember thinking that he looked pitiful. Like a caged animal. I knew it was all in my head, but the longer I looked at him, the more my heart sunk. I felt so enormously guilty in that moment, I couldn’t even look at him.
I pulled my iPod out of my pocket and put on my headphones. I thought maybe that would calm me down. I played some soft, mellow music. I looked at my shoes as I listened. I could still hear the whirring treadmill, the pounding of his feet over my music. I looked up at him, feeling a little more steady. I watched his legs as he ran… they seemed so stiff and tightened. I remember my gaze settling on his knees… I watched them carefully. They swayed back and forth, like fleshy pendulums. The longer I watched his knees… the more I started to see little glimpses in my mind of his legs slipping, of his pace slowing down, of his knees creaking to a stop. The image of his legs slowing down would persist for a moment, and then those pendulums would come back. And then I would see him tripping and falling on his stomach… and then the pendulums would come back. My heart started to beat faster. I was getting more and more anxious, and I could feel my stomach tensing up as I saw Ashton losing the bet again, and again, and again. Yet every time, those pendulums would come back. No matter what I felt, he kept running. I closed my eyes. Everything felt heavy in that moment. It was overwhelming.
I got to my feet. I felt like I was going to throw up. I hurried outside, slammed the “Exit” button to unlock the door, and stood over a hedge in the cold air. I had been in there only twenty minutes, but I couldn’t take it. It was like I was face to face with my own insanity. The anxiety was too much.
I realized that I was imagining my friend truly getting hurt. It wasn’t just an intellectual transaction anymore. I saw it with my very eyes. I thought to myself… What kind of a piece of shit am I that I’m thinking like this? What the fuck is wrong with me?
I walked back to the apartment, just trying to slow down my breathing, trying to settle down my flurried mind.
I called my friend, who woke up in the middle of the night to take my call. I was frantic, “Fuck, I can’t watch them. I can’t. I’m going fucking crazy with anxiety just being in that room. I can’t handle it.”
“Hey, hey. Haseeb. It’s okay,” she told me. “Listen to me, it’s okay. You don’t need to be in that room. You need to just worry about you right now ok? Ashton’s parents are in there worrying about him, he’ll be fine. Focus on yourself. Just calm down, just breathe.”
“Fuck, fuck Rachel. What if he has a heart attack? What if he goes to the emergency room? How am I going to even know? His parents aren’t going to tell me. I was sitting there on that fucking bench, imagining him falling over… what kind of a person does that make me? What kind of fucked up person am I that I’m imagining him getting hurt? What’s wrong with me?”
“Listen, Haseeb. Nothing’s wrong with you okay. This whole thing is just mad. He’s a madman, and he’s brought you into a mad situation, and it’s making you go mad too. Nothing is wrong with you. Calm down, okay?”
“I don’t know Rachel. I don’t fucking know. It was like I was invisible in that room, his parents wouldn’t even look at me. I feel like such a piece of shit. I wish I had never done any of this. I didn’t think it’d ever turn out this way. I thought that it’d be over by now, that he’d have realized he couldn’t do this. I didn’t think I was doing anything wrong by taking this bet. I’m going to feel like a piece of shit even if I win, or if I lose. I don’t know why I thought that I’d be okay with this.”
Things went on that way for some time. Talking to her calmed me down some, but I still felt like there a riotous pain in my gut…something twisting and flopping around inside of my stomach, and it would climb up into my throat and choke me and then sink back down again. I felt like a wretch.
When I finally got off the phone with her I was less frantic, but the bet was still towering over me. The image of Ashton running in that gym kept seizing my thoughts. I tried to browse the internet and keep my mind occupied. It was 7AM. Time was slowing down to a crawl. He texted me his progress, and I measured it up—he had been running almost non-stop since midnight. At 78% of the time he had allotted, he had run 77% of the distance.
As time went on, I would feel more and more anxious. I had never felt an anxiety like that before in my life; it was suffocating. The longer I would be alone with my thoughts, the more it would possess me. I was looking at the clock twice every minute. Eventually I got so fucked up in the head, I had to call someone again. The cycle continued like that. Every moment I wasn’t speaking to someone, it would start to feel like I was drowning in my own mind.
At around 8AM, I called someone who I hadn’t spoken to about this bet before. Her name is Ursula. She’s my best friend’s mother. I met and got to know her over a week when she visited us about a year ago, but I had spoken to her only a couple times since. She is a small, skinny, worldly Polish woman who works as a healer. I remember my leg shaking uncontrollably, staring at her number in my phone. It was 6AM in Utah. My heart was beating. I felt guilty for calling her at this hour, but I dialed the number.
“Hi? Who is this?”
“Ursula? Hi. It’s Haseeb.”
“Oh… Haseeb… how are you sweetheart?” she crooned in her slightly raspy voice. Even her voice sounded sagely to me. “Are you ok?”
“Hey…hey…haha…well…no, I’m not okay,” I sighed nervously. “I got myself into something pretty crazy Ursula. I really fucked up bad and got myself into something I can’t handle. I can’t take being by myself right now. My thoughts are driving me crazy. I’m losing my mind, Ursula.”
I proceeded to tell her all about the bet from the beginning. She murmured little yes’s and oh my gosh’s, and just followed along my story without interrupting me. I told her, “I’m so sorry Ursula for waking you up. I’m so sorry, thank you so much for listening to me… I just really needed to tell someone all this.”
She told me it was okay and tried to calm me down. She told me that I was one of the wisest and most mature young men she knew, and that she was surprised I had found myself in this situation. She told me that ultimately, this would be a great lesson in my life, and that Ashton would be an important teacher in my life as well, whether he knew it or not. “What matters now most is whether you will learn the lesson that life is teaching you now, or if you need to be given this lesson again Haseeb. Ultimately, your challenge is going to be to see this through to the end, to acknowledge everything you’re feeling, and then you must be able to forgive yourself. And once you can do that, and emerge from this without feeling like a victim, you’ll be able to move on in your life, in your mind, and get back on the road you were meant to be on.”
Then you must be able to forgive yourself. This phrase especially stuck with me. Even now, sitting here at my parents’ home in Texas, it reverberates in my mind. I spent three days on the road alone in my car, wrestling with those words. I will never forget it.
I thanked her.
She had instructed me on a breathing exercise to do that would make me relax. I remember the mantra she told me to repeat:
“I trust in the process of my life completely.”
I had hung up the phone and was lying down on my bed trying to slow my breathing. Staring up at my ceiling, I calmly said aloud… “I trust in the process of my life completely.”
In that moment, some part of me became prepared to lose. I knew that I was supposed to lose the bet. That I was right to lose the bet. Because somewhere in all of this, there was a lesson that I needed to learn about myself, and about the world, and I had to accept that it was myself who brought me to this insane moment. 300k was going to hurt, a lot. When I made the bet originally, I realize that I wasn’t really prepared mentally to lose 300k. I could handle it, I’d be okay—money can be made back. But ultimately money wasn’t what really would affect me the most.
I thought about these things for a while. It was almost 9:00 AM. He had three hours left.
I woke up Doug, telling him that the bet was getting close to the end. Ashton’s mileage had now pulled very slightly ahead of pace. It was going to be down to the wire whether he managed to finish. I told him I was losing my shit, and I just needed to talk to someone. He got his clothes on and we went to get some breakfast to calm our nerves.
As we were talking over breakfast, Ashton texted us. He had done 60 miles, and there were 3 hours left to go. He wrote “I’m going to do 10 miles in 3 hours no problem. If you want to buy out now, you can for 200k. As a favor to you.” Doug and I were surprised.
“Man…there’s no way I can take that buyout. To pay 85k to have a shot at a million dollars? I need less than 10% chance of winning to stay in. The last ten miles have to be the toughest. We knew that going in, that it would get exponentially more difficult the further he went on. Ashton has a point at which he can’t run anymore, everyone does. He’s never done this kind of endurance running before. The only question is whether his body will hit its limit at 69 miles or 71 miles. I can’t take this buyout.“
Doug agreed. We told him no. He asked if I was sure, if I really believed that this wasn’t cake for him. I said I couldn’t take that buyout. We didn’t hear back from him.
Before we left the restaurant, I dropped $5 in a charity collection.
We drove home in silence.
By 10AM, Doug couldn’t watch Ashton either. He said he couldn’t handle it in there.
So we waited.
Time dragged slowly.
I was talking to people when I could to keep myself from exploding. But when I was telling my friends about what I was feeling, my tone had changed completely. I had felt like I had already lost. I felt like it was over. I was preparing myself. The number 285,000 would roll around in my head like a ball bearing.
Time was slow.
It was almost noon, and we still hadn’t heard from Ashton. I couldn’t even contemplate anymore what was happening. My mind was starting to numb, and I just wanted it to be over with. I was ready to lose, and I didn’t care anymore… I just wanted it to be over. The bet had begun at 12:30PM the previous day, and it was already 12:00PM. It was truly down to the wire.
I heard the door swing open.
I ran into the corridor at the head of the stairs. I didn’t know what I expected to see. My heart felt like it was being held up by wire strings. In that first second that I saw the scene before me, I didn’t understand.
Ashton was being helped up the stairs by his stepfather. He barely had the strength to pull his legs up. He was gripping onto the rail for support. “Is he okay?” They didn’t answer me. In that moment, I didn’t know.
When he finally got to the top of the stairs, he stepped into his room. He could walk. And then I knew.
It was over.
He had won.
I felt like I should be trying to help. It’s not the time for me to worry about myself, I thought. I asked his mother how he was doing, what they were planning to do to help him recover, if they needed me to do anything. She told me that he was soaking in a tub of Epsom salt to help him recover. They said they were going to bring him food while he was soaking in there. He said he wanted pancakes. She was going to make him some.
I didn’t know what to say. She told me then that they were going to take Ashton back to Ft. Lauderdale for a couple of days to let him recover. She said she would worry about him if he was here with us. It was then, the look that she gave me… as though I didn’t belong there at all, that made it all start to sink into my skin. That’s when it all started to hurt.
I asked again if they needed anything. She spoke to her husband. They ignored me.
I didn’t know what to do anymore. I was exhausted. I went into my bedroom, texted a few people who were closely involved to tell them what happened, and sunk into my bed. I soon fell asleep.
The next couple of days were hard. I wasn’t able to sleep well. I had strange dreams and would wake up after a couple hours. I dropped off Doug at the airport at 5AM the next morning, and from then on I was alone in the house. My mind felt heavy and sluggish.
I remember a friend of mine telling me “Haseeb, this is going to fuck with your mind a lot. You’ve had a tough year, you walked away from poker after getting hacked, and now you put up all this money and lose what seems like an impossible bet. You’re going to have a lot of digging to do, just to get your head in the right place again. That might be what sets you back the most, is just being able to believe in yourself again.”
When I walked around the house, I could see the remnants of everything that happened. I saw bags on the floor full of used Gatorade bottles and power bars. Ashton’s sweaty clothes still strewn across the floor. A half-open bottle of spaghetti sauce. When I saw that, for the first time it made me want to cry.
I decided I needed to leave. Ashton knew I had already planned to leave Orlando on the 14th, a week later. But I needed to leave now. I couldn’t stay in that place anymore.
I didn’t hate Ashton. I didn’t blame him. Everything that I experienced, that I felt, and that I did fell squarely on my shoulders.
That afternoon, I started packing my things.
Everything that happened over those two days made me question a lot of things about my life and myself. I made the drive from Florida to Austin over three days, stopping only to eat, sleep, and write. Ultimately, like Ursula said, I need to understand what this tells me about who I really am. And then I need to be able to forgive myself for what I did.
I’d never lived with other poker players before. I’ve always been something of an outsider to the poker world—almost an interpreter you might say. I’d always been surrounded by normal people living their ordinary lives. Living with these guys has taught me a lot about myself, about who I want to really be, and how I want to live my life.
Something that I’ve come to think about is that perhaps there’s something about the world of poker players that’s fundamentally unhealthy. This generation of online poker players and its culture has existed for less than ten years, yet I’ve always had some assumption lodged deep in my psyche that if I’m not finding happiness through poker that it’s just something wrong with me. And yet, there are so many people at every level of poker who are so deeply unhappy. It leaves me wondering.
And perhaps that’s what really is the most difficult challenge for this generation of poker players. To infiltrate a world that is at its root, deeply unhealthy and imbalanced. To grab this bull called poker by its horns and to try to tame it for as long as we can. We hold on, and the bull bucks and tries to throw us into the droves of insanity around us. Some hold on, some don’t. And maybe some are being dragged along the ground by this bull, and think they’re still okay because they haven’t let go. I remember writing over a year ago that as much as we learn about the game of poker, nobody really teaches us how to live as poker players. Nobody teaches us when we’re supposed to let go of the bull.
In the end, I don’t know the answers to any of these questions really. I’ve thought about a lot of things over the last few days and my mind is still scattered.
Losing 300k is painful. It will make me a little more anxious about money, but ultimately I’ll be ok. I know that I need to put my mind and resolve back together so I can step back into the bullring. I’ll have a lot of work to do to get back to the top of the game. My challenge now is to get myself back onto the head of this bull. And though I know it’ll throw me off again someday, I know I have to ride it.
It’s part of the process of my life.
As I was in the process of packing up my computer, to my surprise Ashton came through the door. He had already come back home the next day. I asked him how he was feeling, and he said he was feeling alright. His knees were hurting, but he was alright. He said he needed a shower. There was a Super Bowl party he wanted to go to that night.
“We should talk,” I told him. He nodded and went to have a shower.
I went outside and waited.
When he came outside, I was leaning against the car when he came up to me.
“This whole thing was really screwed up,” he told me. “I didn’t expect things to get out of hand like that.”
“I know. But it is what it is, and what’s happened has happened.” I looked at him carefully. He was looking off in the distance. It was windy. “I didn’t expect things to turn out the way they did either,” I told him, “but ultimately I need to take responsibility for what I did. You could’ve seriously have gotten hurt, and I don’t know how I would’ve lived with myself if that had happened.”
He told me that he knew his body; that he knew he wouldn’t get hurt. He wasn’t so stupid that he’d agree to something if he thought he could get hurt. “That may be true,” I told him, “and you may have totally believed that. But we didn’t. And that’s what matters.”
He considered this a moment, and nodded.
“It was stupid to make this bet with you,” Ashton said. “I just hope it doesn’t affect things between us.”
“Well, in the end nobody really won man. I felt like shit, Doug felt like shit, your parents felt like shit, and ultimately I know you feel like shit too, even after winning.” He nodded. “I need to figure out some things about myself and my life,” I told him.
“Are you leaving?”
He looked off in the distance again.
“Before I go man,” I told him, “I need to tell you something. You’re still my friend Ashton. Everything that happened was really fucked up, but everything that I’m feeling right now is on me. I still care about you, okay? And I don’t hate you. Even though I need to leave, it’s because of shit that I need to deal with on my own. And if you ever need any help man, you can call me any time. You got that?”
He nodded. He reached out his hand to shake mine. I hugged him. “It was good living with you,” I told him.
He had to go. He asked me if I’d be here when he got back later tonight. I told him I wouldn’t. I was glad that I spoke to him before I left. After he drove away, I went back inside and looked around at the house. I realized that I was almost sad to see it for the last time. I knew that it was the end of an important episode in my life.
I finished packing my car, took with me a couple of the power bars that Ashton had left uneaten, and started the drive home. They tasted awful.
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