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

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.

 

$600 on Super Bowl squares

 

Probably $35 playing knock

 

Same, also had the over 4.5 wins! Only won $200 though, kudos to you for believing in this team more than I did.

 

In High School, I stuck my head in a Chick-Fil-A used peanut oil bin (room temp) and won 3 cases of Moosehead from 3 friends that bet me I would not do it. The ride home was kind of nasty especially since I had to stop and get gas.

 

I have never been one to gamble as I always felt I worked to hard for my money(with the exception of a $2 Nassau in golf no automatic presses

 

I’m not gonna give the specific amount, but many thousands when I placed a pretty sizable bet before opening week on the 2006-2007 Gators to win it all.

 

$600 on a four team $50 parlay.

 

$250,000. Bought a Mustang and a double wide! Lost it all on meth and hookers!

 

Straight up dollar for dollar. $1,000.
Dude thought because he's a neurosurgeon that he couldn't be wrong. He went straight to Google. Upon learning he's lost immediately started with the "oh I got things mixed up."

Sure did. That's why he lost.