The Bookie Chronicles Reprised Part 2

I used to run a blog series on Barstool Sports called The Bookie Chronicles. It was a series that shared degenerative-gambling personal stories from the Barstool community and it was very funny. Mostly because it covered just disgusting behavior that a lot of us find relatable.

In that spirit, I wanted to reprise some of the stories because they were ultimately deleted during the Penn integration. Something about regulators evaluating Barstool as a risk and finding my blog series as evidence of poor behavior or improper standards. Some bullshit like that and then one day they were all deleted.

Unsatisfied with that result, I made the decision to archive every Bookie Chronicle submission for a later usage such as right now.

You can find last week’s blog right here.

As usual, all of these are submitted by you guys. So feel free to send more in to Carl@CarlsBlogs.com.

Let’s get to this week’s submission.

I Suck

Hey Carl, been a gambler for quite sometime now but never really in the big leagues. I’m a small time guy, you know go up a few hundred, down a couple hundred. I had a great start to the year, coming off of the superbowl winning a little over $2,500 and I thought it was the start of things finally starting to look up for me in the gambling world.

I was most definitely wrong.

For a while I using the same bookie, but he only paid out and I only needed to pay when I was up or down a couple hundred bucks. Sounds great, right? Well, come along baseball season i find myself losing every week because I suck.

I eventually go down a little over $200 with this guy and come up with a brilliant idea: If I just keep betting with this guy, I’m either going to go down even more or I’ll just slowly creep out of the hole I am already in.

What do I do?

Well anything the right degenerate would do, let’s find another book to pay the other book! I end up going down a few hundred with this guy, so now I’m down with two seperate bookies and neither guy has gotten paid yet. Welp, let’s do it again!

I get ANOTHER bookie and boom, I’m down with this guy just as quick as I was with the other guys. I finally sack up and pay all of them because I’m not that much of a scumbag and I don’t want to lose my accounts.

Moral of the story is I went through 3 bookies trying to pay the original book, and ended up going down over $700 between all of them. I’m 100% convinced I’m the fucking mush now, I’ll bet overs, unders, favorites and underdogs and no matter what I lock in I lose. The thought of a winning bet before putting it in, but then never locking it ALWAYS wins.

I’m taking a break now from the gambling world to think about my degenerate life. Fading myself won’t work but I think I have no choice to try.

Good luck to all. 

So let me get this straight.

You really thought the solution to losing money was to simply make more wagers? Am I reading that correctly? Because that’s the single dumbest fucking thing I’ve ever read in my entire life. And I’ve got a decade+ around some of the dumbest motherfuckers known to mankind. Yet somehow you’ve found a way to break new ground on an already broken frontier. That – in and of itself – is truly remarkable.

If one bookie doesn’t work, I can assure you the next will have the same fate. And if the first two go down, the 3rd is a lock to follow. Those are but a few guarantees anyone can make in the sports gambling world.

But let’s be even more specific… because it’s not just sports gambling we’re talking about… but the underworld of bookie relationships and the inner-workings of our repeated failures.

These feelings don’t really exist on DraftKings or FanDuel. It’s so much different when you’re losing money that’s already been deposited.

For example: if I’m betting on a credit line, I can get my little tits smoked in the morning and still bounce back that afternoon. You don’t see gambling as a series of individual bets, but rather an entire day on the book with credit. So when you lose, you automatically assume it’s going to get made back in a future bet on credit, which of course only leads to MUCH bigger losses.

Ultimately, the bookie relationship is a much more reckless environment. Although that often creates better moments.

Example: You get crushed to start a big ten football day, but then hit an SEC afternoon parlay to break even after 8 wagers. Life is good and then it’s awful: you get smoked in primetime then double down on the wrong side of the 10pm Hawaii game

All of this happens on credit mind you. No cash is actually moving from one account to other so there’s really no immediate pain.

But then you wake up with a red $1,800 in the top right corner of unclemicksports.com and you want to eat a bullet.

There’s some good moments along the way but it’s just not worth the stress and anxiety and losing all of your disposable income. That’s a hard lesson I had to learn for nearly a decade and it’s kinda embarrassing to think about in hindsight. No matter how you spin it, just a really stupid part of my life.

But again it was also really fun because there’s so much hope and promise that hasn’t been ripped from your hands and heart. You actually think that you can be a big winner and your life will improve because of sports gambling. You still don’t hate yourself. And more specifically, you don’t know that you’re a pathetic loser who will never win money.

So try to enjoy that part of life because there’s no going back once it’s over.

Trust me.

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