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.

 

Prices are rising, which makes everyone look for ways to save money. Sometimes, I want to drop everything and go on a trip with all my savings. It is essential to find ways to distract yourself and save money. It won't solve the inflation problem but it will help relieve stress. Such entertainment is precious during challenging times when every penny counts.

 

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.