Best Betting Stories

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

AMD. I had bought shares last June despite criticisms of the company. Sold my shares off a few weeks ago, easiest money ever made.

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

Had falcons ML in super bowl, got greedy took them again live at halftime for even more

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

Frank: Ten says he shorts it. Livingston: No bet.

• Ocean's 11 (2001)

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

We had a pretty huge gambling scene in high school with around 60+ students playing across the campus.

We once played a game of maybe 9 players and everyone pushed all-in. Total pot was around $750 and I won on pocket Kings. Good day.

I bet $600 before the primaries that Trump would win.

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

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...

Not crazy especially considering how little the lump sum was, but i took my savings allocated for the entire summer (under 5k, im still in school) and threw it into ethereum at $60 a share. Within 3 months it hit 400 a share. Wish I could say I sold at the top.... held on for longer but still sold it all above 300.

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.

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Bought weekly super far out the money calls on $NVDA prior to their last earnings report just for the hell of it. Turned $1.8k into ~$20k.

A friend of mine did bet on Leicester City, the EPL club, they had odds of 5000-1. He bet 2 pounds on them after he got drunk and they went on the win the the tournament

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.

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.

Took a flyer on Brooks Koepka winning the US Open. won $1,000. You wont find a bigger Koepka fan than me now.

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.

All I know is every time I end up the craps table I black out. But man is it an adrenaline rush.

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

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.

If you haven't been to the Kentucky Derby, I would recommend it. Even if you know nothing about horse racing/betting, Churchill Downs is an awesome place and horse betting is an amazing rush.

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