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The Bookie Chronicles

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This is a blog series called the Bookie Chronicles where I share stories from you guys about gambling. You can email me your stories at carl@barstoolsports.com. 

This edition features an interesting mix of bad weather, bad parlays, pony machines and a 50/50 hail mary for the ages. I am so delighted to share these with you, starting with this fuckin guy

NHL Snowstorm

It was a normal winter night with 5 NHL games on the card. I had such a great feeling on the games, so I decided to do a 5-team parlay, throwing $100 down on +1350 odds. I’m sitting home by the fire place watching the games as there is a blizzard outside in the northeast and all 4 7pm games hit with ease. Its now 10:00 and the 9pm game looks like a lock, which is the red-hot Sharks at the league’s worst Senators finish the first period with Sharks up 2-1. 

Boom. Power goes out, no TV, no WIFI, no service anywhere. Here I am 4 out of the 5 games looking like wins and the 5th game looking good so far. As time passes, I start freaking out so what do I do? I take my old worn-down Honda civic for a little ride in the snow looking for service. Oh boy was this a bad idea. 

I try and follow the plowed roads as much as possible until I find myself in the local YMCA parking lot. Finally I get to check the score and San Jose is now up 4-1 in the 2nd. I hang out for a little as I wanted to at least feel comfortable enough with a decent lead before locking in the parlay and drive back home. End of the 2nd, its 5-2 Sharks and everything looks great.

So I decided to leave back to my powerless home and I decide to take the shortcut through my old high school parking lot. I somehow get up the small hill and make a right on an unplowed road. My tires start revving and I get stuck. Throw it in reverse and let’s try again. Same result. I wait a couple minutes hoping for a plow truck but no luck. Try a couple more times and nothing, all I can do is go backwards. 

So I back up about 300 feet back down the icy hill and finally get to turn around. Now that I am going back towards the YMCA, I decided to check the score of the game one more time. 

Terrible idea. 

All of a sudden its 5-3 and I decided to watch the game again. 

Boom! Ottawa decides to score 2 goals in under 2 minutes, tying the game. I sit there with my heart beating out of my chest as overtime begins. SEVEN FUCKING SECONDS into OVERTIME the fucking Senators take a slapshot from the blue line and snipe bar down. Unbelievable, 4 straight goals to lose the final game of a 5 team parlay and miss out on over 1300 bucks.

Lets just say swerving my car into a mailbox on my drive home wasn’t the worst part of my night.

Maybe not the sexiest or craziest story. No one got injured. You didn't nuke the wager. Nobody wins parlays anyways. Blah blah blah. 

Really though this one hits home because it's about the length you're willing to go to watch a game. We can all relate to this. I've put so much malware on apple devices over the last 15 years in pursuit of free live streams, trying to find the right sequencing to close out pop up windows to stop the buffering. Meanwhile you're at a nephew's 2nd birthday party, mom's holding the baby, Aunt Nancy's asking about your next career move and all you want to know is if the Jazz are covering the 1st quarter alternate spread. 

Those moments where you have to grind out the environment to get a good solid taste of your action… those are the moments that define your degeneracy just as much as your unit. 

Elio is the king of this. Sitting courtside, watching puck, chewing threw yet another classic XL Hanes. 

That's what brings me to this guy gliding his used Honda Civic into a snow bank just to see the Sharks lose. The second you left the house that bet was dead on arrival. Anyone with experience knows this. 

This Parlay Sucks

Hey Carl - Fairly new to betting (got started at the beginning of football season) but already hooked. Have been up and down these first few months but mostly down. Well it's the day before Thanksgiving, work is slow and I'm counting down the hours until I can leave. Decide to jump on my book and only have about $60 left so decide to put in a few NHL/NBA parlays in hopes of building a bankroll for the long football weekend. Total potential winnings is about $600.

Going through the night, catching up with family but really just refreshing Gamecast following my picks, and the winners start piling up. On one I've hit 5 of 6 and just need the Bulls to beat the terrible 3-win Warriors. The other I've hit 7 of 8 and only have the Islanders ML against the Kings remaining.

Past midnight and everyone has gone to bed and I'm just up following these two West Coast games alone on my phone. You know what happens next… Islanders give up 4 unanswered goals and lose 4-1 while the Bulls can’t hit a shot in the fourth quarter and lose by 14.

Payday is Friday but now have to sit through the Thursday games without any action and probably watching the Lions lose as usual on Thanksgiving. FML…

I know this email is from 2019 but FML is dead. That's 1. 

2. Rudimentary math says you should NOT be betting. If you need a payday to cover a balance deposit, maybe wait a couple paydays. 

3. Burning your balance on a couple parlays to build a bankroll for a long football weekend is exactly what I describe it to be. Burning your balance. 

Guys. Just be smarter than a complete moron and you'll be A-Okay. 

The Machines Are Coming

My degenerate gambling buddy introduced me to the ponies about 15 years ago. He tried to teach me to handicap races, but I would always just bet the 2-4-7 trifecta box. 

Fast forward to a few years ago. I started handicapping races. We were at the track and I spent a full 30 minutes analyzing the next race. Lo and behold, I hit the exacta and WPS for about $350.

I cash in the ticket and decided that I'm a genius and should bet heavy on the next race. After about 15 minutes of drinking and handicapping, I go back to the machine and bet about $150 on the next race.

I grab a hot dog and a beer on the way back to our table, thinking I'm now the world's greatest handicapper. I sit down with my friend and show him my tickets for the next race. Guaranteed winners.

The only problem is…I forgot to press the cash out button. I left about $200 in the machine.

I go to customer service, they look up the ticket based on my open bets. "That ticket was cashed out upstairs 4 minutes ago. Nothing we can do".

Lost all of my bets on the next race, and obviously the $200 I left in the machine. From the penthouse to the outhouse in about 10 minutes.

I always just bet the 2-4-7 trifecta box warms my heart. Not even fuckin trying. Just throwing Smash-Y Corner in Madden every single play. That's how you move the ball down field. That's how you bet the ponies. 

That said. 

I audibly sighed with a textbook UGHHHHHHHH when he said he left the $200 in the machine. 

That's an unreasonably high fear of mine given that I rarely go to the track and almost never machine-gamble. But alas, still a fear that I miss a jackpot or leave a ticket. 

Anyways. 

That fuckin blows for you dude. 

Sorry.

SPLIT THE POT/SPLIT THE POT

Carl - In the summer of 2018, myself and a few buddies fly from Detroit for Game 5 of the Stanley Cup Finals between the Capitals and Golden Knights. We decide to get there the afternoon before the game and leave the morning after to try and minimize the risk of staying in Vegas too long.

Well less than 24 hours in and trouble managed to find me or I found it you could say. At one point I lost 17 straight hands in blackjack across three different tables. As I head to the game, I’m down just shy of a Dave Portnoy unit. My plan now is to just enjoy the game since after I’m locking myself in my room like solitary confinement until it’s time to catch my flight home.

The puck is about to drop and I notice a girl selling 50/50 tickets. I ask my buddy if he wants to go in as partners but he says no equating it to be “rigged” since neither of us had ever heard of a person winning or even coming close. I look in my money clip and I’m down to my last $100. If I’m going down I mine as well go out firing so I get the max of 300 numbers for $100.

It’s mid 3rd period and I’m up on the concourse due to breaking the seal way too early. I hear the numbers get called and reach for my ticket so I can throw away the losing CVS receipt looking ticket I’ve had to sit on all game. I’m looking down at my ticket and back up at the video board like a bobblehead. Suddenly, it turns into the keno scene from Vegas Vacation as I become Mr. Ellis doing my best “I won. I won. I won the money” impression in a state of shock.

No cash was paid out on the spot, probably for the best, but instead they gave me a Happy Gilmore sized check for $68,340. I let ushers take pictures with it in exchange for getting me nearly on the bench for the raising of the cup. That night we had our own Ovechkin-eque victory celebration with the winnings covering the tab. After taxes, covering my losses, and a hell of a night I turned my last $100 into nearly $35,000 from the biggest bailout of all-time.

I told myself I wasn’t go back to Vegas for a while because nothing would ever come close to that. Well I ended up back in the desert 7 separate times over the next three months using every excuse and justification you can think of. Once again, another plan where Vegas seemed to get the best of me. From that day on, my buddy has asked me to be partners on every 50/50 raffle we’ve ever come across at games, golf outings, charity dinners, wherever. We haven’t come close once. 

Dudes rock. 50/50 rocks. Everything about this is amazing down to the half-a-dozen round trips to blow the remaining balance. What an animal. Probably from Detroit or somewhere slimy. 

And I think 2024 is a guarantee to bring at least one of us another split the pot jackpot. I can feel it in my cherries. For all the ragging on parlays and online blackjack and dumb decisions. None of that matters if it's a raffle ticket with proceeds headed to charity. That's the trade off with 50/50. There's no such thing as TOO MUCH GIVING. 

Any other split the pot winners? I'd love to hear about it. 

Carl@barstoolsports.com