What's the most money you ever won from a bet?

I've profited about $2500 this year in sports wagering since it went legal in NC, but almost all of that was off of free introductory bets.

I am pretty good at baseball parlays. (Player props).

I did make about $500 on on parlay for a Lightning game when I bet on several guys to have assists/goals and they all hit.

 

For the past 14 years, I only bet $25 once a year for the Kentucky Derby. Never won until this year with Mystik Dan at 18-1. Because of that win, I played $25 for Seize the Grey at the Preakness at 15-1 that won. Finally, I bet $50 on Dornoch at Belmont at 17-1.
Not all on one bet, but since they are connected (triple crown), I'll count them as a combined net of $1575 won this year on the ponies. Now that I've bragged on myself, I'll probably go back to losing $25 on the Derby every year from here on out.

 

I won $300ish in the early days of DFF on draft kings. I didn't enter the $20, million dollar with this lineup, if I had it would of paid out $23k or so. My best friend reminds me at least once a year, I laugh in public and punch drywall in private.

 

Wow, I have a story, also in Puerto Rico, was staying at a Ramada in San Juan, took $50.00 to the Casino. DOWN to my last $4.00, played a 3 dollar coin bet , won $300.00.

Kept playing and left that night with about $800.00. Only dang time I ever walked out of any Casino my entire life a winner. Not that I gamble much but I have been to Reno, Vegas and lived in NOLA, never ever came out ahead anywhere else!

 

I apologize, in 06, I placed a $70.00 Bet in Vegas at my hotel on the Gators before I drove to Glendale, got back early that following morning and collected $245.00.

 

My father was the gambler, kind of a whale of sorts at several Vegas casinos. When I was 14 I got to go on one of his trips with a few of his gambling buddies. While sitting in the casino bar during the afternoon a friend gets the idea to give me $300 and wanted my father to do the same. Bartender kicked in another $50. My job was to take the $650 to the closest roulette table and put it all on red or black. I reach over a players shoulder to plunk it down on black and I certainly get looks since i am 14. Pit boss ok’s the bet and I win. Pick up $1300 and return to bar. They gave me $175 in tips for that but I had to do it again with my money. I went down again plunked my $175 down. Same reaction of looks. Pit boss ok’s the bet. Black again, win again and take MY $350 back to the bar. I am 66 now and remember that like it was yesterday. I never really gambled much again.

 

$6.37 in a penny poker game in a basement in Jersey. I was the mysterious out of town guest with my ex-brother in law’s friends. Later I divorced his sister and married my current wife in Vegas. I feel like I won there too, but it’s cost me a fortune!

 

Won about $8,000 on this past Super Bowl. KC ML and the under. That pass to Mecole in OT was glorious

 

since the stock market is like gambling, I bet on Bitcoin (proxy stock MSTR) midyear and I'm up quite nice.

 

I know a guy that won around $50,000 off of a $5 fantasy football entry

 

Walked into a casino with $200 and got two $100 chips. Went to the roulette wheel and played red or black with hundred dollar bets. Weirdly, I correctly guessed red or black three nights in a row at about what seemed like 80% of the time. I know it doesn't make sense, but the tree with the winning numbers followed a pattern and I'd bet in the middle.

Red
black
black
black <-- bet
black
black
red
black
black
black <-- bet
black
black
red

I spent more time looking at that tree than anything else, betting one $100 chip at a time. Again, it doesn't make sense, but whatevs. After the first night I went from $200 to $1,000. The second night I was up to $2000, and on the third night, I decided to bet out into the playing field for the first time. I put a $100 chip on black and a $100 chip on the intersection of 4 numbers. When the ball stopped, I had hit the bet on black (1 to 1) and one of the 4 numbers (8 to 1). After sitting in the same chair at the same table for 3 nights in a row staring at the tree, when the dealer pushed me my $900 in winning chips plus my original $200 dollar bet back, the pit boss came over and told me that I had to leave. They said that they felt like I had too much to drink, even though I know I hadn't. Anywho, I was up to $4,000 at that point. I asked if I could keep the money, they said yes, so I asked where the cashiers were located. I wanted to feel like I really hit it big, so I had them cash out my $4k in chips in 10-dollar bills, lol.

The part that I still lol at is that as I was walking out with $2,000 worth of ten dollar bills in each front pocket, clearly sticking out of the tops of the pockets, the guy at the door said that I might want to take a taxi. I told him that I was good, I was just walking to the hotel next door. He looked down at my pockets and asked me if I was sure about that.. We were in a nice part of town, but it was Chicago. On second thought, I would get a taxi. So, I get in the taxi, he asks where to, I tell him the hotel next door, so he drives out of the casino, takes the very next left into the hotel parking lot and up to the lobby. I peel off a fresh 10-dollar bill since I was flush with them (Dumb and Dumber style) and head up to my room. Shortest taxi ride, ever.

tl/dr - basically $3,800.

 

Most I ever won at once was the pot and $20,000 for drawing a Royal Flush at a poker house where you automatically get 20k if you draw a royal, 10k for a straight flush and 1k for a 4 of a kind.

They took the total taxes from me there so cap gains on the spot so minus that.

At once anyway.

 

What?!?! With all respect, something is missing here.

I believe the run happened. I believe your whole story but your inference that they threw you out is almost unbelievable because they didn’t want you betting any more. They would have wanted to keep you betting because doing what you were doing is almost a guarantee that you were gonna lose your money back.

If that happened and you weren’t actually just too drunk (a phrase I’ve never heard from a casino, that’s why they give you free drinks), and you’re not even betting much at all. So little that it would have flown below any pit bosses “we need to watch” radar.

If you were doing that betting 10s of thousands they MIGHT come and offer you a free room to make sure you stayed there long enough to lose your money.

it’s almost impossible to cheat at roulette.

Now regardless of how much money you were betting if you were breaking the statistics at a BJ table they might not care about the low 100 dollar bets and the how is he winning over and over on crazy things like standing on a face card when the dealer is showing 6 but there is nothing in roulette that sounds warnings unless you’re betting a ton on crazy pays:

THE only thing that would get you thrown out of a casino in the above situation is if in fact you were too drunk and acting so or perhaps you weren’t tipping? But trust me (and I was a Vegas assistant pit boss for a couple years) they would never have thrown you out for that. Something missing here.

As I was reading your story play out, I was waiting for the part where you lost all your money.

They like when people feel invincible on all the table games because they bet more and statistical anomalies can happen but it’s a mathematical fact that eventually on Roulette you WILL lose. Roulette is for a play or two.

Say you lost 11,000 playing games and you want to get your money back, put it all on black or red and be done with the win or the loss. Yes you were getting lucky but that won’t keep up. And the reason the black/ red isn’t 50/50 is simply because of the two greens. Things like the two greens make billions.

When you start parlaying, it’s practically asking them to take your money and they would in no way kick you out over thousands. On big money tables, thousands can happen in a single bet. Even 100s of thousands. Something missing, but I’m not saying you’re lying, to be clear. But I can say FOR SURE, they didn’t stop you from playing for 4K. They wouldn’t even comp you for that. 30 years ago maybe but they wouldn’t waste time playing with mortgage money.

Sorry if you feel I’m coming down and calling you a liar and far be it from me to insinuate you made this up but I can GUARANTEE with this info you were not thrown out for sitting at same table, looking at tree, or for anything else here.

They would have tried to keep you there. I think maybe you were just plastered and someone complained? Maybe?

Look, I’m just saying if you tell this story to someone that is a high roller this is what they will think so, brotherly help. All love.

Glad you had the fun run. It’s always fun to feel like you have the claravoince to see the cards. I like poker (because you don’t play the house) you play other players but it’s fun when you win either way. Congrats.

Also; do you have a photographic memory because how in God’s name did you remember every black, black, red etc order! If you have photographic memory you should go reek havoc on the poker tables and watch for tells or maybe even single deck Bj but they will kick you off there and it’s easy to see signs of counting.

 

general rule of thumb is don’t bet on your teams because of emotional variables like we can beat Georgia with our 18th string QB. But if you know we have a walk on that will actually be playing and he’s pretty good, maybe take the money and bet. Stuff like that. Especially in small market college teams there is still good iq bets by checking local papers on what’s going on. The moves on those type of games are highly volatile and I made a killing betting on small market teams. One of my favs was old school TCU for some reason. TCU before they were the modern TCU once made me more money in a year personally than my job.

If it wasn’t for the stigma of saying I’m a pro gambler and the eyes it makes roll; I probably would have done it with sports and poker (the main two games where you play people instead of the house so you can win), and I was in the 42% range and if you bet right, that’s pro level. But it’s higghhh stress.

 

Hey man, if that’s the worst part of your marriage, may God keep on blessing you with a lovely wife and life.

 

Nearly $300 from an office pool. We were allowed 2 entries and that year is the year we won March Madness for the 1st time. Both of my brackets had us winning it all so both of my entries won. I wasn't allowed to enter a bracket ever again after that.

 

Bro... lol.

I do not have a photographic memory. That was not the exact order, just similar to what happened, ffs.

 

There was a FM and a hold on them too

 

I don't really gamble but I won $450 on super bowl squares once. I had the correct numbers the next year but the teams were reversed.

 

Just won $500 on the win tonight! Had bet Gators win > 4.5 regular season games. Was very much in doubt when Lagway was carted off in the Georgia game.