Today’s the five-year anniversary of one of my most secretly amazing nights, and I figure that’s a good enough excuse to end the secret. I think I’ve told this story to fewer than twenty people, which for me is a VERY low number.
So I’d come into possession of a “gift certificate” offering two free nights in a decent Vegas hotel in exchange for sitting through a timeshare sales pitch. Timeshares are a scam, but the free hotel stay felt like scamming the scammers. I booked it in February 2019 and invited my friend Yichao to make the drive from LA and spend a guys’ weekend together.
Yichao picked me up at the airport and we made the most of Vegas for 48 hours (the correct duration for any Vegas trip; no more, no less). We wandered the Strip, went to Drag Brunch, got confused by slot machines, and ate an alarming number of calories. (Did you know there’s a $100 all-you-can-eat buffet? Now you do.) Oh yes, and I dutifully sat through the two-hour timeshare sales pitch and repeatedly told the guy that I was not his target market before finally being released.
On our second and final night, we walked across the highway to the Rio Casino to see Penn & Teller (great show). As we filed out of the theater, I suggested to Yichao that we dodge the crowd vying for taxis and Ubers by having one last round of blackjack before we headed back to the hotel.
A nice call on my part; I went on a hot streak, turning my $200 or so into almost $500 in less than an hour. As is common, our blackjack table had an optional side bet: for $5 you can bet whether any of the three cards in play—your two cards or the dealer’s up-card—would be a 7. If one of them is a 7, you win $10; two out of three, it’s $100; three out of three, it’s $1,000.
You shouldn’t need long with a calculator and a deck of cards to realize this side bet is for absolute suckers (even more so than gambling in the first place). But I think of gambling as entertainment, not investment, so I tossed a $5 chip into the side bet circle as the mood struck me, just for the tiny dopamine hit.
You see where this story is going, so I’ll tell it as abruptly as it happened: shortly after midnight, I placed a fateful side bet. I was dealt a 7. And then the dealer got another 7. And then I got a third 7.
Yichao and I leapt to our feet, yelling and high-fiving and generally causing a scene. Moments later, though, I realized something was wrong; the pit boss was interrogating the dealer in a serious tone, and the third player at the table was waving us back to the table. Maybe I hadn’t won after all?
Nope. In all the excitement, I hadn’t noticed something: it wasn’t just three 7s. It was 7s of the same suit. Which meant I’d won the jackpot. Which stood just north of $32,000.
Should I say something profound here? My life is so stupidly privileged that it beggars belief. I didn’t deserve this lucky hand more than any other idiot at the tables.
As you’d expect, there’s some paperwork involved in winning jackpots. We sat buzzing for an hour or more at the table, sharing the story with passers-by and sipping free drinks (generously tipped) while casino management scoured the video footage for any shenanigans and had me complete a tax form (W2-G, if you’re curious). Yichao said he was just as happy as if he’d won himself; I’m sure I’d feel the same way if it were reversed.
At last, the floor manager decided the necessary boxes had been checked and instructed the dealer to pay me out. An interesting ritual: he counted out the full jackpot in chips from his tray, then immediately separated $7,000 of it into a separate tray for tax purposes, which the pit boss whisked off to the back room for the accountants to play with.1 The remaining $25,137 was pushed in a big pile over to me, just like in the movies.
Apart from the millions of little butterfly-effect coincidences that conspired to enable this win, there’s one incredibly large sliding door: I hadn’t been placing side bets on every hand. There’s an extremely plausible multiverse where I *don’t* drop a $5 chip in the circle, the exact same cards are dealt, and I watch my jackpot float by unclaimed.
The point here is NOT to obsessively place sucker side bets! The point is that I got very, very lucky.
Even after everything was settled, we still hadn’t actually played the blackjack hand! I foolishly said “hit me” (Always split 7s against a dealer 7!) and busted out. I left the dealer with a generous tip, scooped the pile of chips into my wool hat, and nervously walked the 20 steps from the table to the cage. It was another half-hour wait for them to tick more boxes and print me up a certified check2, during which I called Kiki with the news. Finally they handed it over, and just like that I had a flimsy piece of paper making me $25,137 richer.
Well past 2am, we taxied back to the hotel. I said good night to Yichao, telling him not to worry about paying for his end of the Penn & Teller tickets or anything else he owed me. Though I’d already warned myself against extravagant spending, I did splurge on a first-class ticket back to Austin—Spirit Airlines just didn’t seem right.3 At the airport the next morning, I made video calls to immediate family to share the news, and checked approximately ten times per hour to be sure the check was still okay.
The Aftermath
Back in Austin I deposited the money with my credit union. The exchange with the bank teller was funny; neither of us wanted to be the first to comment on how big a check it was. I soon made a category in my Quicken app called “Holy Crap,” which proved to be genuinely helpful.
About 25% of the winnings went to pay the remaining balance on my FEMA loan for my 2016 house flood. Another 10% paid for fun stuff: tickets to see Hamilton when I met Kiki in New York the following month, my flight to Amsterdam a couple of months later, and some toys for around the house. (And yes, I made multiple charity donations.)
A month or two later, all of the rest went towards my Chevy Volt, which belatedly offered me some close contact with my winnings. I figured out that Chevy Volt prices were $1,000 cheaper up in Dallas than in tech-happy Austin—well worth the road trip. Since my credit union didn’t have a branch in Dallas, literally the only way for me to have money on hand was to withdraw it in cash. So I did, and for 24 hours I got to spend some quality time with my winnings before handing it off to a Dallas Chevy dealer.
So that’s my casino story, which (now that the money’s gone) I don’t mind sharing publicly. It wasn’t life-changing on the scale of winning the lottery—if I’d only gotten two 7s instead of three, I’d be writing you on the same MacBook from the same Amsterdam couch.
But man, am I glad I placed that side bet.