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What’s the craziest parlay you’ve ever hit?
Posted on 8/16/25 at 9:03 pm
Posted on 8/16/25 at 9:03 pm
Football season is right around the corner and with it degenerate gambling. What are the best bets you’ve ever hit (by legs, size of winnings, or long odds)?
Posted on 8/16/25 at 9:07 pm to Decisions
I’d prefer hear about biggest losses.
Posted on 8/16/25 at 9:11 pm to CollegeFBRules
I've only done sports betting at bachelor's parties. One of them was like a 5 team parlay for the first college football Saturday. $50 bet would have paid like $400. I thought I had that in the bag because they all seemed like huge miss-matches.
House had my money before the 3pm games started.
House had my money before the 3pm games started.
Posted on 8/16/25 at 9:16 pm to Decisions
watched a friend of a friend win 100k on the rams super bowl 2000. he was from st louis and bet preseason for them to win it. I believe it was $500 at 200:1. Maybe $200 at 500:1. watched it with a crowd at the tahoe biltmore
not that 100k isn't good money, but this was when we were all mid 20s. the whole place was watching and went nuts when he won

not that 100k isn't good money, but this was when we were all mid 20s. the whole place was watching and went nuts when he won
Posted on 8/16/25 at 9:37 pm to Decisions
Getting laid off with severance and bonus 2 hours before receiving an offer letter with my resignation notice sitting in my drafts folder ready to send 
Posted on 8/16/25 at 9:41 pm to PikesPeak
quote:
Getting laid off with severance and bonus 2 hours before receiving an offer letter with my resignation notice sitting in my drafts folder ready to send
Did you buy a lotto or powerball ticket after?
Posted on 8/16/25 at 9:42 pm to Boss13
quote:
I've only done sports betting at bachelor's parties. One of them was like a 5 team parlay for the first college football Saturday. $50 bet would have paid like $400. I thought I had that in the bag because they all seemed like huge miss-matches. House had my money before the 3pm games started
I had a friend on a bachelor trip lose a 10-game parlay, albeit mostly ML on heavy favorites, by one leg. That leg being the Miami/GT game in 2023 where they fumbled late because they didn’t kneel.
Posted on 8/16/25 at 9:43 pm to Sunnyvale
$100 to 27k
10 team ncaab mens basketball opening day 3 years ago. Home team, top 25 ats
10 team ncaab mens basketball opening day 3 years ago. Home team, top 25 ats
Posted on 8/16/25 at 9:53 pm to Decisions
I don’t gamble much but did hit a 6 team parlay on Labor Day weekend at Caesars. I don’t remember every team but one was FSU with Winston. $300 barely covered the drinks that day lol. I had another parlay that would’ve done real good. Hit 7 out of 8. If CC wasn’t a choke job against Boston I would’ve ate lobster that night.
Posted on 8/16/25 at 10:07 pm to Decisions
Longest play I ever hit was +23000 2002 NCAAB Finals Kansas vs UNC exact score 69-72.
I was balls deep back then and had pre game bet my account down to $1.00
I threw that dart, it hit and couldnt sleep that night. Won $230 but jesus christ the "what if" kept me up for days
Also hit both sides of the spread live plus some props.
I was balls deep back then and had pre game bet my account down to $1.00
I threw that dart, it hit and couldnt sleep that night. Won $230 but jesus christ the "what if" kept me up for days
Also hit both sides of the spread live plus some props.
Posted on 8/16/25 at 10:10 pm to Decisions
Went to the Golden Nugget in Biloxi 2 or 3 years ago and won 3,600 on a slot machine on a 68 cent bet on a Sunday morning.
I had just gotten there and won it on Free Play.
I had just gotten there and won it on Free Play.
Posted on 8/16/25 at 10:12 pm to Decisions
"Parlay" is French for "I have a gambling problem "
Posted on 8/16/25 at 11:23 pm to East Coast Band
Won roughly $1,500 on a $10 NFL 10 game parlay (which included a 100% boost).
Lost those winnings with a month or two.
Lost those winnings with a month or two.
Posted on 8/16/25 at 11:33 pm to Decisions
Football season before last, week 16. I had just signed up for 2 different sportsbook apps and had a total of $565 in free bets. I placed a 15 leg parlay of heavy favorites with a $365 bonus bet, then placed another similar 14 leg parlay with a $200 bonus bet. They both ended up hitting for about $4k without spending a single dollar.
Posted on 8/17/25 at 12:05 am to Decisions
Best was a 9 team for 1600. Had some good weekends but never hit a 9 game parlay. I did it because I hate uneven numbers
Posted on 8/17/25 at 12:14 am to Decisions
I hit a 6/6 ML way back in the early internet days ~1995. No real time updates. I had to wait until about 2am to see if Arizona St. hung on to win. It was $10 for $400. That seemed like all the money in the world to me back then.
Posted on 8/17/25 at 6:23 am to Decisions
quote:
What are the best bets you’ve ever hit (by legs

Posted on 8/17/25 at 6:49 am to CollegeFBRules
quote:
I’d prefer hear about biggest losses.
A guy at my office was about to win $500 on a Super Bowl pool. Had the 1-1 square.
Tampa had a pick six on the final* play. Oof.
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