Best Betting Stories

Whats up Monkeys. I woke up this morning and checked to see if anyone has made a post about ridiculous betting stories, and saw no one has. Even though the days of Gutfreund and Liar's Poker at over, finance still attracts the type of personality that enjoys making big and sometimes ridiculous bets. Last night I saw one of my buddies lose a few hundred bucks over a game of Madden, nothing huge but it made me curious. So, what is your craziest betting story? Really looking forward to hearing your responses.

73 Comments
 

Betting 10k on Madden and letting the computer simulate the game.

I'm talking about liquid. Rich enough to have your own jet. Rich enough not to waste time. Fifty, a hundred million dollars, buddy. A player. Or nothing. See my Blog & AMA
 

Wasn't my bet luckily. No clue who won or how that is an exciting bet

I'm talking about liquid. Rich enough to have your own jet. Rich enough not to waste time. Fifty, a hundred million dollars, buddy. A player. Or nothing. See my Blog & AMA
 

I'm addicted to everything but gambling. Never gambled in my life. Don't see the appeal

heister: Look at all these wannabe richies hating on an expensive salad. https://arthuxtable.com/
 

No way. Not with my personality. I like my life. I would like to learn to play poker some day.

heister: Look at all these wannabe richies hating on an expensive salad. https://arthuxtable.com/
 

I bet 1 set for $1K in tennis and lost...

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

I was down almost a grand sports betting one week back in 2015... As a college student this was basically everything in my bank account. That saturday night I put 1.5k on McGregor winning the Aldo fight almost 30 seconds before the fight started. If I lost I would have at least a grand down in debt, but a minute and one Mcgregor KO later, I was the happiest college sophomore on the planet. Since then, I've never put anything more than $20 on one bet, luckily learned my lesson without losing money like I've seen so many others my age do

 

Not bad. Are you puttin $20 on McGregor again?

I'm talking about liquid. Rich enough to have your own jet. Rich enough not to waste time. Fifty, a hundred million dollars, buddy. A player. Or nothing. See my Blog & AMA
 

My university roommates pooled their cash and bet $20,000 that UConn would beat George Mason (You don't understand basketball surferdude! It's a LOCK!)...

They also pooled their rage and did an extra $20,000 worth of damage to the house that night.

 

One of my roommates who was loaded bookie put 100k on UNC beating Duke a few years ago when UNC was a clear favorite. UNC Lost... Kid wouldn't come out of his room for a week

 

My thinking was there was a bubble of sell outs and politically correct politicians who didn't get anything done. So Obama winning twice pumped up the bubble to it's max and when Americans turned on the TV and it didn't represent what was going on we weren't happy. We saw higher taxes, a weaker military, and a growth in non-substantial jobs. He wasn't the best candidate, but he was what America needed to pop the bubble and correct the political atmosphere. It is pendulum theory.

 
"Paul Allen's Business Card" I bet $600 before the primaries that Trump would win.

What site do people use now? It used to be InTrade....

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

5 team MLB parlay when I was ~12 in vegas, my brother placed the bet for me, $5 won me ~$125, happiest kid ever watching those games, plus back then i could get away with watching the games in the sports book

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The about four people who bet that Leicester would win the Premier League last year. That's the one time you bet with your heart thinking it will never happen and you put down like 10 bucks and at the end of the season, you have 50 grand in your pocket and to top it off your team that wasn't even top 10 last year has magically made history.

 

I know an older guy who won $750k in blackjack in Vegas in less than 1 hour. Sounds sexy until you start to wonder how much he's lost over the years...

 
"three.commas" I know an older guy who won $750k in blackjack in Vegas in less than 1 hour. Sounds sexy until you start to wonder how much he's lost over the years...

Yeah blackjack has too low win percentage for me.

Expert card counters get something like 54% win rate....

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

My first bet: Went to the Royal Ascot horse races and thoroughly studied the info pamphlet to select which horse I wanted to bet on. Placed my bet on a horse that seemed to have great potential based on its racing history but still offered a good payout if it won as it wasn't the clear favorite. Race starts and I cheer on my horse, which appeared to be doing quite well and was approaching the lead. Then it tripped and fell and was severely injured. They had to set up a tent around it and shoot it dead on the spot. I felt so horrible about it and still feel somewhat responsible for killing the horse that I rarely if ever bet anymore. I worry that I will cause harm to anything I bet on.

 

You know, the best part of the best drug in the world isn't the high. It's the moment just before you take it. The dice are dancing on the table. Between now and the time they stop, that's the greatest high in the world.

Get your facts first, then you can distort them as you please.
 

I had a family member liquidate his entire 401(k) and concentrate it in one stock, which I protested fervently. The stock doubled over the next two years and he exited his position.

The company went bankrupt about 4 years later, lol.

 

Knew a guy who bet something close to $3k on 2016 election. He had multiple bets with different people. Chose Clinton and lost it all.

 

Technically this wasn't "betting" because I didn't put any of my own money on the line at the time, but the best ROI for me was entering a ~50-60 person free roll holdem tourney hosted by a card room and winning $1100 for coming in third place. You got a pretty small roll of chips for the free entry, but were allowed to buy 2 or 3 extra stacks for $100 a piece at the beginning of the tourney. I made the decision to not put any extra money on the table and just see what happened.

The starting stack was so small that you would basically get eaten alive by blinds within the first couple rotations of the button, so you needed to make a move early to build a stack. It was definitely designed to encourage the purchasing of extra chips (I think roughly 80% of the players bought extra--most the max amount you could buy). I played tight for a few hands, then raised heavy with a decent hand in late position. Ended up all-in quickly against a couple other players and won big. Did this a few more times and somehow found myself at the final table. I was a student at the time, so I was so pumped to finish in the money at 3rd. Good times.

 

Don't call PETA - in high school we organized a huge beta fish tournament ring. Met in the park and your buy in was your fish +$10, the bracketology behind that was great.

More recent - had a friend give me 20:1 on $100 that Spieth would blow the Master's at the turn on Sunday. Hated seeing him implode but I bought his AP2s with the $2k I won. :)

 

Friend of mine gambles a lot - won like $20k or something one day - deposited it all into his bank account at the ATM for the company he works for. Something like 20 transactions in a row of $1k each. Ended up almost getting fired and having administrative leave for a few days. Used admin leave to go gamble more and won even more - showed up at the last admin meeting with a bunch of $1k chips.

 

I bought BAC at ~$3/sh and GS at ~$49/sh back in the early part of the financial shitstorm that was 2007-2010.

Both have paid off quite well.

 

Draftkings golf, especially in non-majors, is easy $. Just go overweight on a few guys that are poised to do well and you'll end up in the black more than not. I average ~12% a week

 

Can't give you a good answer...have only really used Draftkings and Bovada. DFS golf is solid because there are websites out there to help you project player ownership, and it turns into a bit of game theory. I take shares on players I don't really like because of low ownership. For example. Bubba is like 2% owned this week.

If you do decide to try it out (next week is the PGA), I suggest using fantasy national golf club. Free online model & lineup generator...takes a lot of human error out.

 

I have a good one:

I went to a casino with my granny because she likes to play the slots. Please keep in mind my grandma is a thug who likes to smoke cigars and drink whiskey (I couldn't say no). She played with the nickles and I finally hit up the blackjack table. I ended up losing about $800 and shitting my pants. Then I made $1000 and walked out. Worst and best day of my life. I learned that casinos are nothing like the movies. That shit is addictive and real, but I like to play poker with my friends.

 

This post has evoked some nasty flashbacks. I actually feel a bit sick

Absolute truths don't exist... celebrated opinions do.
 

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