Barstool Golf x THE PLAYERS Championship Collection | SHOP NOW

The Bookie Chronicles

Shutterstock Images.

This is a blog series called The Book Chronicles where I share reader emails about gambling. I ran the series a couple years back but stopped when Penn acquired us because these stories are bad for that kind of business. Last thing I wanted was a state gaming commission penalizing the brand because I celebrated some decades-old story of a man's quest to recover his dead bookie's life insurance policy to fulfill a delayed child support payment. Or something like that.

I figure enough time's passed that we can harmlessly revisit some old, unpublished submissions from late 2019/early 2020 provided we agree on the following:

- 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 

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

My Coworker, The Degenerate


A coworker of mine is an absolute degenerate in every sense of the word. He's easily lost over a hundred thousand dollars in his lifetime gambling on sports. This year when football season started he found out he’s been cut off by every bookie in town. He’s in his 60’s so online books are out of the question for him. He knows I use an online site so he asks me about placing bets through me. 

I've heard him tell a million stories about how much money he’s lost, so I figure I’ll tell him I’m placing the bets without actually placing them. I say yeah no problem, but if you use credit they lock the account once you go down $500 (totally untrue if you aren’t familiar) in order to make sure he doesn’t go down more than he can pay, and so that he can’t dig himself a massive hole.

Every single Saturday he’s gone up $300-$1,500, and every single week by Tuesday he’s down $500. Every single week. 
Once he hits +$500 the bets just get bigger and bigger until he loses it all on one game. It’s the stupidest things I have ever seen. It’s literally impossible to cash out gambling like that. I’ve got $5,000 of his money in a shoebox to cover it if he ever does decide to cash out while he’s ahead but I don’t believe he ever will.

The lesson here is to ALWAYS gamble with discipline. I’ve always heard it but when you’re on the other side of it you truly see how impossible it is to win gambling recklessly.

This is everything I want from you guys and more. You know your colleague is a degenerate but you still want to help out. Like the Cool Parents that lets their teenage kids booze in the basement because you know they're boozing anyways. That's the same level of relationship here: allowing utterly destructive behavior to occur on the principle that it's under your control. Only difference is that you're not responsible for the legal repercussions of your 60 year old cubicle mate the same way you are that stupid 16 year old. 

In any event, the support here is critical. Having a guy help you find a book was an elite feeling. I remember my first like yesterday. The introduction was so valuable. 

My friend's dad gave me a phone number to call and leave a voicemail. The message greeting would say "Good morning, good afternoon and evening sports fans. Today is November 29th and these are the numbers. Giants 3, 44. Bears, 6 and 37. Vikings 2.5 and 45…" and on it went in rapid fire. 

He'd have every major line every day at 10am. NHL, NBA, NFL, MLB. You'd have to call a couple times to write the numbers down because he talked so fast. When you were ready, you left a voicemail starting with your username (Carl number 7, Carl number 7) and then you had to state your balance before placing your bets. Everything he said was priced -110. 

"Carl number 7, Carl number 7, minus 660, minus 660."

I got absolutely fucking destroyed over the next couple years but it was awesome. Customer service was unbelievable. One year I got a box of skirt steaks delivered for Christmas made out to Carl #7. 

Anyways. Getting off track here.

Point is this story warms my heart. Two generations coming together to bridge a technology gap with a personal touch to mitigate losses with the complete understanding that your coworker is NEVER going to win. That's such a strong bond and it pains me to recognize it's a fading presence in today's society. 

Shoutout to anyone helping anyone find a guy out there. Your efforts will always be valued.

8-Team Rebound For A Complete Moron

Hey Carl. You posted a story of mine earlier this year. You called it cute and innocent that I was mad enough about a $10 parlay to write an email. Just thought I would give you a not-so-innocent update.

I was exploring my website the other day and made the stupid decision to click the casino tab. I did this despite a personal promise to limit my monthly losses to $100. Nothing crazy.

I play a few games, had some ups and downs early on but then got hot playing blackjack.

I turned my $100 into $350 in a matter of 20 minutes.  

As a college freshman, thats a fuckload of money. That's like 3 workdays. Anyways, I close out of the website up $250 feeling like the biggest badass of all time. 

The next morning I lost everything. Reload money, lose. Reload more, lose. New website, lose more. I was down $500 by lunch. In a matter of two weeks, I had lost about two weeks worth of work money. Saturday comes and I remembered that earlier in the week I placed an eight-team parlay risking my last $2.50 to win $437.

1. Florida -25.5

2. U of I +14.5 (no brainer)

3. Ohio St. -42.5

4. Notre Dame -8

5. Purdue +1

6. USC +1.5

7. Baylor -2.5

8. Iowa/Wisconsin over 38

If you remember anything from those games, you can probably tell I was shitting my pants throughout the day. U of I with the late comeback, Purdue with the last second comeback, USC with a defensive stop to win, Baylor barely winning in overtime, and Iowa/Wisconsin hitting the over late in the 4th with a field goal. 

Well, I won back most of my casino debt with that 8 team miracle parlay. Of course, I went on to lose another $100 to the online blackjack but I have sworn to myself (again) to steer clear. Not so much of a happy ending but I'll make sure to tell you first when I win big in blackjack.

You're never going to win big in blackjack. You never emailed me back and I never want to hear another word from another person who seriously thinks online blackjack is anything better than the absolute worst thing on earth. 

With that in mind, I think almost all of us can relate to the different phases of emotions here. Step 1: you start gambling on sports. Step 2: there's no sports on but you want to gamble. Step 3: you find the online casino. Step 4: you personally recognize the absurd risk while simultaneously budgeting for monthly losses. Step 5: you win money. Step 6: you immediately lose said winnings. 7: you lose the initial bankroll. Step 8: lose another round of funding. 9: LOSE MORE. Step 10: get the parlay calculator out and start saying your prayers to Our Lady of Guadalupe.

If you have personal experience with that cycle then get in line with the rest of us. 

New Website = New Life

How the hell are we Carl?

Last year I graduated college, landed a decent job, and finally had a steady stream of income to inevitably lose on my online book. 

I usually stick to college hoops, NBA, NFL, but never really bet on NHL. I remember coming into work one day around the time of NHL playoffs and talking to a buddy of mine. He followed the league and was telling me about how the Tampa Bay Lightning were heavily favored to win the cup, apparently they were having some sort of super season. 

All I heard was, "lock, lock, lock, lock" Bet on the fucking lightning, it's a lock. So I did just that. Right before the Blue Jackets - Lightning series I put in a bet, it was something like -300 for the Lightning to just win the series. I was SO confident after my buddy gassed them up, I put 500 dollars on it.

As you may know, the Lightning got their shit stomped 4-0 to the BLUE JACKETS.

It was 3-0 in the series, I was slowly realizing I was going to have to pay out my bookie soon. Then, I got the text. The most glorious text message I have ever received in my life.

Bookie: "Yo, my boss told me we are moving books, here's your new login…."

Me: "What about my open bets, will those transfer over? I got a Capitals future thats gonna cash out"

Bookie: "Nah man, sorry about that.."

Of course I lied and said I had a future that was looking good, not about to tell him about the lightning bet. 

What are the fucking chances. 1 game away from losing 500 and we switch books and bets don't carry over? Best text I have ever gotten. 

There is nothing and I mean NOTHING that compares to the revelation that you had a new website and new login. Especially if you were carrying a negative balance but not enough to hit the payout threshold. Say you're -750 with a $1,000 threshold, then it just disappears because the Ukrainian servers got wiped overnight. No records are left. No evidence there was even a website in the 1st place. is closed for business folks.

That's called a clean slate and it's fucking awesome. Granted, $500 on a -300 future might be the single dumbest thing I've ever heard. So dumb you actually deserve nothing but mercy for exercising a functional life in spite of an abject neurological disorder. 

In other words you're my guy. 

Rookie Virgin

Hey Carl,

Rookie Gambler here

This after this past weekend, I was up 339 after betting a crap ton on Notre Dame covering the spread against duke and a risky NFL parlay (Vikings and Steelers money line, packers cover the spread). Anyways I was pumped to be up this much after being down 81 after last week (a lot for college kid which I am). Since I was up 339, I decided to go crazy this week. I bet a 4 game NBA parlay Monday night for 10 bucks that was 3 for 4 (of course), then decided to bet 180 that the bruins cover the -.5 spread against the Panthers. B's up 4-0 going into the third and of course the Panthers rally back to make it 4-3 late in the third. I wasn't in full panic mode, but then of course the Panthers Score to make it 4-4. My heart sunk. Would've been up 479 which is INCREDIBLE to me. Being down 190 this week absolutely sucks despite being up all time, and is a lot of pain to process for a rookie gambler in college. 

I know this is a mild story but I'm fuckin DYING at how specific this guy is. Up 339I bet 180… would've been plus 479… down 190. 

I don't say to shame. It's more to celebrate that specific phase in life where you're tracking everything in an excel spreadsheet where your unit is $1 and the future is ever bright. You think, confidently: this will be a good use of my time

Believe me. It's not. 

You're just enabling and empowering negative self talk about all the bets you could have/should have/would have won but for __ (insert routine sports occurrence). It's not unique, just depressing. And nobody will ever feel bad for you.

This Is Exactly What A True Degenerate Sounds Like


Dubbing this the 11/11 Make a Wish Monday Miracle, feel good story to give hope to those in the trenches:

Carry over Seattle Parlay Sounders -.5, Seahawks +6 because was throwing feelers Sunday.  (Shitting my pants riding the Browns -2.5, Jets ML all day). Sounders hit the first leg proceed to double down calling 49ers frauds all day. 

Typically dick around on Monday’s throw a few bets out there Monday, nothing too serious trying to pad the account for football later in the week. 

Feeler parlay Celtics -3, Rockets/Pelicans U 246.5, Memphis +11.5, Raptors +10. (Side note buddy has a beat in Grizz 1H ATS 9-1 to date ride that shit). 

1st 3 ^ above drill pretty easily and I go to hedge by hitting the Clip Show to come out with money no matter what. (Did the same thing last week EMU/Cincy +24 or some shit and they almost won outright, was depressed). Got Clippers -9.5. Won by 10. Pushed the third leg of the parlay and hit the hedge for max ROI. 

Seattle parlay hit too. 

11/11…where dreams come true


I did not add that VIVA. 

In fact, I added nothing to this entry. It exists in it's purest form without editorial combing for presentation. That's to best capture the full scope and depth of your fellow degenerates. Hit the hedge for max ROI couldn't be scripted for fiction without eliciting a gross collective eye roll. 

Nice thing is you can't fake this mindset. It's authentic and real and this guy exists. He's probably got an open 5-teamer with a Champions League group stage future to close. Just needs Antwerp to score at least one 2nd half road goal to push on an alternate cumulative total for the extra gravy. 

You have to be careful with these guys in a group text setting because they'll light you up around the clock. But otherwise they're good people to keep close. That's how it is with most of us. 


Thanks for reading. 


email to share your story