What’s the Most You’ve Ever Won/Lost Gambling?

Screen-Shot-Oceans II poker gameThe closest I’ll ever get to real gambling is reading the beginning of Daniel DerondaOther people in my family have an intrepid streak, though. For a while there my father was hooked on playing the stock market. Once, he told me, in quick succession, he made $50,000 and then lost 30K of it, so he went home and told my mom, “Hey, we made $20,000!” Another family member who shall remain nameless got hooked on internet poker back in the day and had to wean himself off in part by putting his salary in the care of someone else.

For some people, clearly, the excitement is worth the risk. This intense Vanity Fair [<- FIXED] piece about a cocktail waitress making bank by running a private poker party for the beautiful folks of Hollywood, Inside the Viper Room — an excerpt from the upcoming memoir of Molly Bloom (no relation) — captures some of the reasons why. It also contains some discomfiting details about Tobey Maguire, who brings his own vegan snack food to the game.

It was all incredibly surreal. I was standing in the corner of the Viper Room counting ONE HUNDRED THOUSAND DOLLARS IN CASH! I was in the company of movie stars, important directors, and powerful business tycoons. I felt like Alice tumbling down the rabbit hole. As the players filed out, they thanked me, some kissed my cheek, but they all pressed bills into my hand. I smiled warmly and thanked them in return, trying not to let my hands shake. When they were all gone, I sat down in a daze, and with trembling hands I counted $3,000.

Not a bad way to make $7,500 in a night.


23 Comments / Post A Comment

ATF (#4,229)

I think the most I’ve ever won is $100 but I’m not a fan of gambling. I don’t get enjoyment out of something I know I can’t win. Like, if slot machines were a game I could get better at, I’d be all about it.

My brother once won $3000 on a lark. My parents live in Las Vegas (they teach high school; it’s a looooong story) and we usually spend the holidays out there. Because it’s Christmas time, there’s not always actually time to go gambling, which had largely been the case on this particular trip. It was our last night and we were out to dinner at one of the local Henderson casinos. We’d eaten and my brother wanted to spend the money he’d brought along to gamble with. I forget why but we didn’t have a lot a time for him to do this, so he sat himself at a Lord of the Rings slot machine and kept hitting max bet – thinking it would be the quickest way to lose his money and/or make a bit. On like his fourth spin, he hit some crazy bonus and the end result was $3000 in winnings.

chic noir (#713)

@ATF wow was it a penny machine? A post by your brother on his big win would be so neat.

bgprincipessa (#699)

Like… maybe $10.

$15000 on a $5 slot machine in the Borgata. They gave me a 1099-MISC on the spot!

Lily Rowan (#70)

@forget it i quit That is awesome! I can’t imagine playing a $5 slot — I get uptight enough playing 50 cents a go on penny slots….

madrassoup (#929)

@forget it i quit Did you take a helicopter home? That’s always my fantasy when I walk into Port Authority on my way to AC. I’m like, “screw you plebs, I’m using my winnings to ride back in style.” I always say the same thing on my way back to Port Authority, too. (I guess that’s my answer to the question in the post.)

@Lily Rowan It was completely a lark! I was just waiting for a taxi to the airport and put in the remains of my winnings for the weekend. The security person who paid it out and gave me the 1099 was kinda peeved at me for not having a comp card.

@madrassoup I seriously thought about extending the trip and renting a Ferrari but if I won in AC, I’d definitely go the helicopter route!

Lily Rowan (#70)

@forget it i quit AHHH! So good.

Worgchef (#6,838)

@forget it i quit You know, I always thought 1099-G was the gambling one. A quick google shows that it is for “Certain Government Payments.”

This reflects my relative interest in both gambling and taxes (almost none vs unhealthily fascinated).

I found a $20 on the floor of the Bellagio, took it straight to a blackjack table and wagered it all. I got a 20, the dealer got 21. Easy come, easy go.

Lily Rowan (#70)

I’ve never won or lost anything crazy, but I do love to gamble! The best was in Vegas a few years ago, I was down several hundred dollars playing blackjack over the course of a weekend, and won it all back in my last few hours before getting on the plane. That was exciting, but, again, less than $500 either way.

Lily Rowan (#70)

Now I just want to talk about gambling a lot, and also how Tobey Maguire is an enormous dick.

pinches (#3,520)

I bought a $2 scratch lottery ticket to celebrate my 18th birthday and won $5. That’s as much gambling as I’ll do…

madrassoup (#929)

It was Vanity Fair, not Vogue. It’s right there in the link!

I read that piece last night/this morning and found it fascinating in terms of how much money she made in tips (like one night she brought in $50k) and was curious to know what that changed in terms of her lifestyle since she was always worried about being fired thanks to crazy-eyed Tobey Maguire. But I don’t find her writing style compelling enough to read the whole book, especially since, if the article is any indication, she recreates the most banal conversations. Never has the act of winning and losing so much money in so little time come off as so boring.

@madrassoup true! fixed.

Lily Rowan (#70)

@madrassoup Agreed. Also, I thought being coy about who people were was weird.

Allison (#4,509)

My “gambling” has been confined almost entirely to football or March Madness pools. (Uncle organizes, mom usually covers my buy in so what little I win ends up going back to her.) I think when I was studying in Australia I took advantage of being old enough to go into a casino to try a slot machine, but was sad by how digital it all is.

skyisfalling (#3,769)

I won $200 on a $2 scratch ticket once, but that’s pretty much it. It was right before Christmas, so a couple of people got extra-nice presents.

RiffRandell (#4,774)

Probably $20 on various failed racing bets. Thus, several thousand fewer dollars than my boyfriend has lost gambling.

NoName (#3,509)

I’m not sure how much I’ve won total, but I usually win on the unusual occasions I’ve gone gambling. I think people who are serious gamblers have cultivated enormous mental discipline which intrigues me.

Lila Lapine (#6,382)

Won: $25
Lost: $0
When I was 9 or 10 years old my family went on a trip to Nevada, and my dad gave me a quarter to play the slot machine at our hotel. $25 in quarters came tumbling out! Then the angry casino manager came and was like, why is there a child playing the slot machine? My dad let me keep the money, and I haven’t gambled since. I figured I should quit while I was ahead.

Heather F G (#6,074)

$96, when I drew Fusaichi Pegasus from a hat for Derby 2000. I was twelve. We start early in Kentucky.

chic noir (#713)

Lost 150 in Vegas, I had a free room for three nights. Won 500 on a two dollar scratch off.

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