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.