The Bookie Chronicles

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This is a blog series called The Book Chronicles where I share reader emails about gambling.

I figure enough time's passed from being regulated that we can harmlessly revisit some old, unpublished submissions from late 2019/early 2020. If you want to contribute your own, email me carl@barstoolsports.com

Some pregame notes: 

- These are your stories

- They're anonymous

- Gamble responsibly 

- The emphasis is nostalgia for the time before sports gambling went mainstream. Before all this fancy technology and synchronization and small talk. A time when having a vice meant something. That's the sweetspot.

- Gamble responsibly 

If you have a legit gambling problem and need to talk it out then you can also email me and I'll help you as much as I can scout's honor. Some of this stuff can get pretty fuckin serious and while there's a lot of funny things about that process, you don't need to let it control you. If no one else is, I'll be your guy carl@barstoolsports.com. 

And let me emphasize that point again real quick. One of these stories is dramatically fucked up and I'm including it because it can help someone else. It should give you some perspective on how bad and personally embarrassing things can get if you're reckless. And please trust that I hate to be debbie downer off that bat, but it's worth me being explicitly clear. The last story is not funny. It's a reference point for rock bottom. 

With that, here's a fresh batch of dumb shit: 

I'm Juan Burgundy?

What's up Carl, love TBC should make it a daily column not weekly.

So my buddy and I were sophomores in college betting with a good friend of ours from high school. He was a local bookie backed by some bigger guys, but we never knew the what the real story was. In college, my friend and I, let's call him Rodger, thought we were sharps, and gambling was our main source of income. Usually we'd go up/down about 100/200 a week and we would always settle up on Mondays. 

One week me and my friend were both down about 275 each. Keep in mind that we are more drinking/drug degenerates than gambling degens, and we spend about 90% of our money on alcohol and drugs, so in college 300 was a fortune. Since the bookie, let's call him Juan, was our good friend, we figured whatever we'll pay him eventually when we can, and we were putting it off until his higher up guys started texting us saying we need to pay. We found out these "higher up" guys were just his friends phones he would text us from to scare us a bit. 

Fast forward to New Year's Eve. Me and Rodger are out at a bar, and we see Juan. We make a few jokes about owing him money and he says "you gotta get me the money ASAP", but we know he's not gonna send a guy to break our legs or anything. Juan then asks if we want shots, of course we say yes. We get wasted, and Juan invites us back to a party with his friends from a different college. We agree and head to the party with him. 

At the party he continues to feed us vodka until my friend blacks out and we get kicked out of the party. We all uber to a deli to grab some food and Rodger passes out in the backseat sitting next to Juan (I'm in the front seat). Bookie Juan reaches into Rodgers pocket and checks his wallet to collect his debt. Coincidentally, Rodger had $300 sitting in his wallet. 

The next morning Rodger says "Fuck. I have no clue how i spent $300 last night what the fuck did I do" and i told him i had no idea, not knowing that Juan had robbed him (to be fair it wasn't really a robbery because it was technically his money but still). 

A few months later, after I was kicked off the book, I paid off my debt I was chilling with Juan, when he told me that he cleaned Rodger's wallet to collect the debt. Rodger still doesn't know til this day, and ALWAYS brags about how he stiffed the bookie.

Even when you think you won, you still lose.

Juan is still a thief. I think that's important. One illegal activity does not then authorize or enable a counter illegal activity. So I'm a little soft on lifting the cash, although it sounds like Juan had no choice. Faking a chain of command via text message was very much his last card to play, which brings me to this. 

Juan must be a huge pussy or (at best) the most nonthreatening bookie of all time. At least from the sounds of it. You guys are laughing in this guy's face on New Years Eve. He has no control over the situation. Poor Juan. 

And at the same time, you guys suck more. Not paying up is bullshit. That's the only reason bookies exist in the 1st place. We pay each other. We agree to a sanctimonious relationship that precedes the written word. I owe you, I pay you. You owe me, you pay me. One hand washes the other, we both wash the face. Make sense? 

Hopefully.

And hopefully you guys don't find that too amusing. 

Horse Racing Expert

This past May I woke up on a crisp Saturday morning to multiple texts from my buddy. He was going on about how he had just stumbled upon a horse racing sharp on Twitter named Marco who was selling his picks for the Kentucky Derby that evening. His bio stated that he had been involved in and gambling on horse racing for over 40 years. And get this - If you had placed $400 on his package of picks from last years Derby you would have made $8,300. 

Within a matter of 30 minutes my friend convinced me to split the purchase of picks with him ($40) and I was on the way to an ATM. I pick him up and we head to the local casino where we both ended up placing $400 each on the picks that we purchased. I had gambled on horse racing before as our local casino has a track but never more than $5 to $10 on a single race. Placing that large of a wager on a single race was an absolute rush and the picks came from a sharp so they were guaranteed winners right?

My buddy and I saddle up at a bar near the casino as we wanted to be close by so we could cash our winnings right after the race. After a few beers and a long couple of hours waiting for the Derby to start, our talks about what we were going to do with our winnings subside and we start having some post betting remorse. We both start to feel pretty stupid trusting picks from a random guy on Twitter we knew nothing about.

The race starts and I truly thought I was going to have a heart attack. Afterwards we took a look at our bet slips and SURPRISE we hadn't hit big for $8,300 like the picks did last year. We hadn't even won our $400 back. All 13 of the bets lost and we were left with $0. 

There is absolutely no worse feeling than losing that amount of money in the span of 2 minutes. I was only a year out of college and had no business gambling that much that day so for the next few months every time I checked my back account I would add $400 to my balance and think about how much I would have if I hadn't bet that day. We laugh about it now and chalk it up as a "funny expensive story" but I will never forgive myself for getting talked into buying picks from a random guy on Twitter.

(Picture attached is the guy we bought them from. This guy 100% looks like a horse racing expert, right?)

Yes. That's a man who can read the ass chalk and understands track composition variables as they pertain to each gait and stride length. Reader glasses and a lucky goatee. Salt n pepper side burns. The cold confident stare of a man with inside information. Everything about this man says horse racing expert. 

And while I'm typically skeptical about the handicapping industry, I would easily put horse racing as the most likely sport for me to buy picks. In other words, I'm on this journey with you vicariously. We made these bets and lost our money together. 

Sometimes that happens. And the comforting thing is you have no basis to outperform this guy than sheer luck. So maybe you could've broken even picking your ex girlfriends birthday numbers or boxing a heavily favorited exacta. That's not why you went to the track in the 1st place, but it's an alternate reality. You can consider that. 

But also consider that you wanted $8,000 at the end of the day and that means buying the information. That means having a plan and committing the budget with full faith. You even partnered with a buddy in the process. So to me, you've got the right formula just need a couple more responsible repetitions and that big day should be coming. 

I Would East Stu Feiner's Ass

Sorry for the poor grammar.

Before NFL season started I decide I’m going to open a bovada account. I start betting  20-30$ a game pretty much breaking even for the first 5 weeks. I then show my dad how easy it is to bet on my account. So he starts saying give me 50$ on whoever. He gets to about 300$ on my account and hasn’t had to give me a penny because he just hadn’t lost. So I’m watching barstool sports advisors and stu Feiner offered a free pick on Sunday’s via his email. I then proceeded to bet 300$ 4 weeks in a row and Stu went 4-0 on all those picks. I gave my dad the 300$ He originally won and pocketed the rest.

I like a short quick hitter and we like that. 

Question, kinda unrelated. When he says "sorry for the poor grammar" is he talking about how to use a $ sign correctly? I'm so confused. Is that a Canadian thing or am I on Mars right now. 

Either way, shoutout Stu Feiner for catching a heater for this kid. The tone and tempo of the story suggested this was going south but alas Stu's free picks were red hot. Nobody catches fire like Stu in the same way nobody eats ass like the guy. He's elite. 

That said, I also play the house for my dad on big games. This past weekend we maxed out Army because Captain Cons converted us to Army guys. That's a different blog. But point is we watched the game in his garage and he asked me for a 50% piece of a max bet. It was awesome to share that moment with him and I'm lucky he's not texting me 2nd half Bulls action. Just when we're together hanging out having a couple, smoking Binny's cigars around his propane space heater. That too is good living. Shoutout to good Dads. 

Asian Women's Tennis

I am a pretty broke college student, and I decided to start betting on my friends book 4 weeks ago. I was thinking I would make a half dozen $10 bets a week. Fast forward 4 weeks to today, and this morning i placed 67 live bets on mid-level professional Asian women’s tennis, betting game-by-game on these matches. I was throwing 20, 30 bucks on a single game. By 1:00, I was up $223 off of my 67 bets thinking I had found a way to break the book. 3 hours and 80 bets later my account was at -40. Asian women’s tennis was my online blackjack. Never again

This is a funny downward slope. Losing $40 on 67 bets isn't nearly as bad as making 67 bets. That's not borderline psychotic as much as it's full blown looney toones insanity. Like lock yourself and throw away the key or maybe find a different hobby. May I suggest woodworking. It requires the same amount of mental focus given the inherent physical danger of maneuvering raw materials around machine powered saws. You'll get the same stimulation from building a balanced end table as you will from live betting midnight Chinese table tennis. 

Anyways that's just my two cents, and personally I've followed some WTA from Stuckey back in the day when nobody else was talking about it. That 2012 run was special if you were there. Lucky to reflect with some success although my bigger sentiment is that I was a pathetic 25 year-old trying to pay credit card debt off free twitter picks. It didn't work in the long-run. A mutual fund would've made more sense but I had to learn the hard way.

This Story Is So Fucked Up That I'm Uncomfortable Posting It Without A Full Disclaimer That This Guy Is An Unmitigated Moron And Complete Scumbag

Sup Carl,

Got into gambling my junior year of high school thru my friend's college brother who was an agent for an offshore book and got me and my buddies our own accounts. Started off slow placing a few $10 bets a week, and go up $30-50 each of the first five weeks or so. All my friends were losing and I felt like a fucking god. I should also mention I was a fiend and was stealing money from my parents and older siblings wallets to buy all the weed and xanax a kid could want. They started to notice the money going missing so had to stop with the stealing, but luckily I now had what I thought was gonna be a constant flow of money coming from gambling. My cocky ass decided to up my unit to $50 and start betting on every NBA game every night, thinking I was about to put my friend's brother out of business. Well…ended up down around $350 after 2 nights. For some reason we were trusted enough with $1000 credit each week, so there was plenty more to play with. It was only wednesday and book settled every monday so I knew I had time to win it back. But…I couldn't handle the stress of it all anymore, so I went and bought 20 bars with the last of my previous winnings. I put three or four $50 bets down and took three of the xanax. 

Woke up the next morning in a deep haze, checked my account, balance was somehow at -$800+. Next thing I remember is waking up in the hospital next to my parents, who were as pissed off as I've ever seen them. They tell me that I was so fucked up in one of my classes that I could barely walk or talk, so the school called an ambulance who took me to the hospital to get my stomach pumped. They show me the bag of xans that they found in my backpack, and I see 5 pills in it. There were 20(!!!) of those bastards to begin with. I must've just taken a handful and swallowed them down like a dumbass. I slowly begin to remember how fucked I am and ask for my phone. My parents told me that one of my friends found it at school and was holding onto it for me. I had gone from thinking I am a gambling god to crying like a baby in a hospital bed telling my parents how much money I had lost in a matter of days.

I lucked out because losing $800 is apparently not a big deal compared to almost killing yourself, so they said they'd give me the money as long as I stopped betting and that was that. The hospital put me in a damn psych ward for like 8 days, so I had no access to the internet or the outside world in general. I finally get out and go straight to the computer when I get home (still didn't have my phone) to check the final balance and what stupid ass bets I had placed to get down so much. I go to the "history" tab and will never forget what I saw next. I had ended up +$1900 after putting my last ~$200 of credit on a 3-leg parlay on wednesday (the day I went to the hospital). The three bets of the parlay? Two NBA unders and a +300 ML. I had bet nothing but spreads up to that point, so I must have just clicked three random lines in my barred out state as my final stand. My parents ended up paying me $800, so I came out up +$2700 when it was all said and done.

I was am still in awe from this wild ride 5 years later. It still did not fail to completely fuck me up mentally to the point that I changed my ways and have been clean and sober since. Well…mostly changed my ways because I still am gambling everyday but now do so responsibly. 

Moral of the story: Don’t do drugs.

I've read a lot of dumb shit. Done a lot of dumb shit. Seen a lot it and so on. Certainly enough to scatterplot and categorize it into different buckets which is good context for me to say this guy really sucks. And I want to be nice and understanding. This story is 4 years old and there's a good chance he's moved on, or so I hope. 

But I have to work within the sandbox of the story right now and that sandbox is infuriating. 

Smoke all the weed you want, bros. You're probably not bothering me.

Cold beers and some vino with the old lady? That's called good living. 

Hard booze, much more circumstantial. You know the time and place for right and wrong. 

Xanax (and benzos generally) is where you really have to start drawing lines. There ain't nothing recreational about that stuff. Just plain old fashioned selfish use, and while a lot of you quickthumbs are about to rag me, let me beat you to the punch with a sad truth. I watched a very close friend completely unravel firsthand in our late 20's/early 30's from mismanaging prescriptions, which is about the nicest way you can put it. And that's one of many friends, which is an extremely shitty reality of our generation. Not really the time to expound but I want to be open and honest about how sad this makes me.

Showing up to class over the legal limit after a long night of bar crawling is part of college culture. Although it's a douchebag move, that's going to happen. 

Elsewhere, this sequence of events is categorically indefensible

Not paying Mom & Dad back instantly, trash 

Going to the computer after 8 days in a psych ward, trash 

Blacking out in class, trash

Deep throating 60mg of xanax, trash

I respect a good time as much as the next guy but please get your shit together so I can celebrate the next great parlay. Nothing beats a late night miracle but in this case, my joy is in reserve. 

Please be responsible in all respects. That's my best advice. 

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That's it for this edition of Bookie Chronicles. If you have a story to share or just need to vent through your own mistakes, please email me carl@barstoolsports.com. I will help the best I can.