Have an interesting story... was done in St. Maarten about 25 years ago - when I was still a youngster, with my girlfriend. She hated gambling, but I was already into betting sports - and it wasn't as easy to get bets down back then. So I had to have action every day.
Went into the local casino in town, the only one with a Sportbook back then. Checked the lines, and saw that Northwestern was a 15 point favorite at Ohio State (hoops). Back then, NW was terrible. I talked to the bookmaker there and told him flat out that his line was wrong - it was reversed. He said "no way - I get them straight from Vegas". I insisted that it was wrong and that he would get pounded on this game. He stood firm. Since he did, I asked him how much I could put down on the game - and he told me $1,500.
Well, now he had me second guessing myself. Back then, there was no internet (except in Al Gore's mind). The only way I could confirm if I was right or not was to find a USA today (where we all used to get the odds each day on games - on the last page). Only place on the island that had the USA today was the airport - and they didn't get the current day's paper until 4:00 eastern (game started at 7:00 eastern). So I went to the airport where I had to buy the paper - they wouldn't let me look for free - which cost $2.50 for a paper that sold for $0.50 back then. I wasn't real happy about that, but they flew it in from the States, so I guess it was fair.
Anyway, I got the paper, and sure enough, Ohio State was a -15 favorite. So, I went back to the casino and asked the bookmaker again about the game - telling him that I saw it in the USA today and saw it was wrong (I forgot to bring the paper with me - we had to stop back at the hotel for umm... well, it only took a few minutes). The bookmaker stood firm on the line. I asked him if I could take a credit card cash advance to play the game. He sent me over to the cashier's cage.
Now this was a small casino. I was able to get a cash advance of $1,500 - which was primarily $10's and $20's. So I had this huge wad of cash, in small bills, which I put on the game. My girlfriend was pissed - thought I was crazy to "waste" this much money. I told her that the Bookmaker was being an idiot and that this was a sure thing. So I took Ohio State + 15 for $1,500. No, I didn't feel guilty, as I pointed out the line mistake over and over again to the BM - and he refused to change the line.
So, we are out at a different casino - no sports book - later that night. Again, there was no internet, nor TV's there, other than a small 19" TV that was showing Headline News. For you older members, you'll remember the days when you would sit glued to the ticker on Headline News, on the bottom of the screen, waiting for your score to scroll by - which seemed to take forever. Well, I didn't even check the score until when I thought it was late in the game - and Ohio State was up by 20. They ended up winning by 17.
So, the next day I go back to the casino to collect my winnings. The BM was a complete dick to me. "How could you bet the game when you knew the line was wrong?". Of course I told him that I told him I thought it was wrong multiple times, but he was convinced that it was correct.
He did pay me - ONLY because Ohio State covered the -15 "correct" line. He said otherwise he wouldn't have paid me, and would have kept my money. I'm sure glad that didn't happen, because down there, I'm sure I would have had no recourse and have been screwed.
The BM paid me, then made me feel very guilty for winning and demanded that I put that money back in play that evening. I ended up playing 4 games @ $250 each - and split, losing $50 in juice. Didn't go back - was happy to be up $1,450.
Of course, my girlfriend was now excited and said "she believed in me the whole time", which lead to another stop at the hotel for a few minutes. Needless to say, the rest of the trip was a lot of fun.
Sorry this was such a long read - but I thought it was an interesting story, so I thought I'd share. That was my biggest gambling win to date, although I've won probably 20 different fantasy baseball/football/basketball contests over the years that have paid $10,000 or more. And I've taken down a number of "bigger" contests in FanDuel the last couple of years.
But the St. Maarten bet was the coolest!
