Note: this post is raw and unedited. I typed it at the airport and on the plane, and posted it as soon as I landed. Please excuse any typos/autocorrect errors/lack of formatting/math that doesn’t add up.


After an insane heater to start the year, including my first ever hand-pay ($1202) and a second $2160 handpay two months later, I am feeling invincible.

Halfway through the year, I have already managed to set my yearly Vegas trip record at 7.

I feel like I can’t lose.

A couple times, I dig myself an early hole, but after tapping into my reserves — which are flush with newly-won cash — I pull off a miracle to make it a winner; Jesus turned water into wine, and I turned losses into wins.

My bankroll, full of accumulated winnings, exceeds $5000 for the first time ever, so I make the decision to invest the remainder into a vacation fund; just like the restaurant at the Strat, I’m on top of the world.

Let me walk you through some of the lessons I learned on my winning streak.

February 2023. International waters on a Carnival cruise. I have a free room thanks to a casino match offer. I bring a few hundred to bet, and on my first night and first time playing Buffalo Ascension, hit a $1202 stampede in free spins for my first handpay. Having won, I reinvest a bit and hit a $500 major on a firecracker machine and a regular at the blackjack table. I go home with the cruise paid for, future VIP offers for free rooms with $500 of free play secured, and $800 more than I brought. Lesson learned: highly volatile slots will eventually pay out big.

March 2023. Fremont Las Vegas. I’m gambling my ass off and treading water all trip after seeing Taylor Swift in concert (my coworker and I both got them at face value, and traded tickets… like I said, I couldn’t lose). I call my shot and say I will get a tattoo if I can run up my TITO to $200. My friend says I should cash out once I dip below my floor of $100, but a few spins below $90 I hit a $140 bonus round to lock in my card shark tattoo. Lesson learned: going below your floor pays off.

April 2023. Mirage Las Vegas. I’m down $600 on the trip, and I hit a $1000 quarter Royal Flush on a bartop machine (next to my mom, who has been there for all 3 of my quarter Royals) to instantly turn a losing trip into a winner. Lesson learned: the cards are eventually due for a big hit.

May 2023. Ameristar Black Hawk. I come up after a concert at Red Rocks for a free night, and low roll knowing I have work the next day. I quickly double up $100 on craps after nailing a yo for my first bet. I plan to go home with this, but decide to throw a bit in Ascension before driving back the next day. I lose $300, but am not content to leave the maxed out machine, so I hit the ATM for more ammo. I’m impatiently smashing the button knowing that I need to leave for work soon, but that the machine is primed. A Buffalo runs at me, I hit a gold stampede, and my $1 bet turns into a $2160 handpay (and an unexpected stop in our Denver office to take a call I couldn’t get home to Colorado Springs in time for). Lesson learned: don’t quit chasing until you get a big payout.

June 2023. Wildwood (now Golden Nugget) Cripple Creek. My cousin is visiting, so we stop by the casinos. I bring $300, but hit the ATM for $200 more after rapidly burning through my money. I go full tilt and Hail Mary my last $100 on 3 line quarter Double Double Bonus poker. On my final $30, I’m dealt four 4s with an Ace kicker, for a cool $600. Lesson learned: up your denomination when you’re losing so you can win it back.

I’ve been applying all of these lessons since, yet I haven’t logged a winning trip since June.

In fact, I’ve lost about $2800, or a month’s worth of my take home pay, in the past 3 months. My gambling bankroll has receded from a high water mark of $5,000 to $1,600.


My opening vignettes are fun, but they don’t include some of the losing sessions I’ve had.

May 2023. Off the coast of Ensenada, on the Carnival Dream. I’m gambling for 6+ hours each day, and have run over $15,000 through the machines based on point accrual. I’ve barely seen the ocean I’ve been so busy chasing a Buffalo stampede or firecracker ignition in the casino. I even find myself skipping shows or getting impatient at lounge music acts wanting to get back to gambling. I’ve already blown through my $500 budget I brought, so I’m charging the room to get slot credit. I see that Buffalo Link is up to 1492 gold buffalo on the 2¢ denomination. Knowing it will hit by 1800, I justify bumping my bet to the minimum $2/spin, reasoning that it will dig me out of my hole when I hit a big hit. I burn through $20, $40, $100, and $200 without hitting the bonus. I’m in too deep to quit, and am almost nauseous as I smash the spin button in a daze. A crew member tells me the casino will be closing in 30 minutes, which only accelerates my sense of urgency and desperation. I finally hit the bonus, and it isn’t enough to dig me out of my hole fully, but I’m grateful that the damage isn’t too bad. I hyperventilate in the room and tell my friend that I’m worried that I find myself continuing to chase, but I’m still back in the casino the next day. After a 5 day rollercoaster, I end the trip down $500, which feels like a blessing given how bad it could’ve been. I vow not to chase any more, take a breather when losing, and to stay within my comfortable limits.

July 2023. Grand Z Central City. I meet my friend for a night of gambling. I bring $300, which I promptly blow through (including a particularly brutal run, where I burned through $100 on single line quarter DDB in the time it took the burger I ordered to cook). At the bartop, I borrow $60 from my friend, hit a quad, and bump up to 50¢. I hit three quads, including two premium ones, within a span of 5 minutes. I am now at $500, and up $100 on the night. I plan to cash out at $400, but miss the cutoff and get greedy. I continue going down like a lead balloon, and bump up to dollars hoping for a few decent hits to get back to $400.

Then $300.

Then $200.

Then $100.

Then $0.

I borrow $60 (in $20 increments) from my friend to chase on Huff N More Puff in a last stand effort, but blow it all on minimum bet without hitting a single feature. I end the night down $560. I vow not to lose more than $200 in a local again.

August 2023. Bally’s Black Hawk. I meet my friend for a quick post-concert gambling session. I bring $300. I start off strong, running up my bankroll at $5 craps before the table turns cold. I buy three numbers when I’m shooting and take full odds (you gotta believe in yourself, right?) only to PSO. Down $100, I go to blackjack, where I proceed to lose my remaining $200. I hit the ATM at Ameristar and proceed to blow $100 more on slots, playing like a zombie and not even enjoying the game, until I snap out of my daze at 4am and decide to go to bed down $400 on the night. I vow not to play if I’m not enjoying it, and to stay out of the locals until my Vegas trip.

August 2023. Black Hawk Ameristar. Okay, you caught me red handed. I know I said I wouldn’t gamble at the locals, but I get an offer I couldn’t refuse: a free NCL cruise certificate that requires I swipe my card at the kiosk. “What’s the harm in risking $100?” I ask myself, noting that I’m already there. I am planning to pick up a last minute ticket to the Ed Sheeran concert in Denver that night, so I plan to swipe my card, get my cruise, get a free Starbucks with my comp, and go for a hit and run. I tell myself that if I double up, or win enough to cover my ticket, I will cash out. I hit quickly on Buffalo, and have enough to cover my $42 ticket. I could have ran with my free ticket, but instead I decide to play down my remaining money on Super Times Pay 3 play dimes, which quickly turns to 5 play dimes as I chase and tap into my winnings. I end up leaving down $100, having lost all I brought and $60 of winnings. I curse myself all the way to Denver for the $200 swing, since I could’ve been up $20 and seen a concert. I vow to stick to my floors and cash out.


Enter September 2023.

With all of my bad habits in full force, and none of my lessons learned, I head to Las Vegas for my cousin’s bachelor party. I bring $900, not knowing how much they would gamble and not wanting to be held back, and reasoning that it’s really two trips in one since I’ve got the bachelor party at the Flamingo Wednesday/Thursday, and a solo night at Four Queens Sunday into Monday.

The trip is exactly what you’d expect; you don’t need to be a sharp oddsmaker to know that the chances of me losing money are -10000. But since I’m a Minnesota sports fan, I’m a glutton for punishment and enjoy rehashing pain and what-ifs.

I blow $500 the first night. It starts out slow, and I’m up and down. I throw in a few $20s to chase on a Chronos machine in the Bellagio cause the bachelor crew is putting me up to it. I break even, but my cousin urges me to keep going. I proceed to lose that $40, plus an additional $60. During this chase-a-thon, the bachelor party moves on and I promise I’ll catch up.

Spoiler alert: I don’t catch up. To the crew, or in gambling. I proceed to blow $100 on Regal Riches, finally hitting a weak minor for $58.

The crew is at Caesars Palace, and I am still in the Bellagio alone. I put my TITO, and an additional $100 into Dancing Drums, without a good hit. I get three different free spins, and the random selection twice gives me the lowest amount of spins (3) and the least amount of reels (5), so it’s not surprising I don’t win.

I walk back to Flamingo with no cash left, and the crew is already in bed. I go to my room and advance $100 cash from the next day’s budget. I’m planning to meet Pennys4Vegas, but don’t make it out of the casino before losing that $100 on the Koi Dragon Tiger machine. I head back up to the room for another $100, which I put back into the same machine. I finally hit the bonus, and head to meet Mark with $60 of ammo. I blow all of that on 3 line quarter poker at the Bellagio sportsbook bar as Mark tells me “nobody does Vegas like you do.”

I walk back to my room at the dirty bird at 3:00am with an empty wallet, broke, and $500 in the hole.

I proceed to blow another $200 with the crew. We head downtown and I hit two quarter Bonus Poker Deluxe quads at Circa to cash out $200. I would have given this back too, but the bachelor got too drunk and needed to go back to the hotel. Even in my degen fugue, I wanted to save on my Uber, so I went back with him (but not before blowing $40 in 5 minutes of Pai Gow play at the Four Queens). I blew $20 in Huff N More Puff as a post-In N Out nightcap and went to bed down $700 on the trip.

The next day, I blow $100 while waiting for the rental car. I hit four 4s in my first hand of nickel triple play DDB at Chandelier Bar, but instead of cashing out my instant triple up, I proceed to give it back and lose another $40.

I chase on Pompeii without hitting anything, and would’ve tapped into the $200 I stowed away had it not been in my backpack that was checked at the bell desk. I seriously consider hitting the ATM, and the only thing that stops me is the fear of judgment from the group. Ironically, one of the groomsmen jokingly asks “has anyone ever told you that you have a gambling problem?”

Utah is a welcome reprieve from the gambling, and I head back to Fremont Street ready to watch the kickoff of football season and gamble.

I throw $20 into Ascension and run it up to $45. I tell my friend that I’ll cash out to buy a Vikings hat if I hit $50, but I hit $0 and am in for $40 more before I walk. The Vikings lose, which puts me in a bit of tilt.

I play some $3 video BJ with him and run my $40 into $95 before ultimately cashing out at $60. I borrow him $100, which he Venmos me for.

With only $60 in cash and knowing yhat I will likely hit the ATM to withdraw the $100 from my original budget as well as some karma donations, I don’t have high hopes.

I hit on a few games at Golden Nugget, running up my $60 into $300. I’m on a run, and hit 3 different machines for a $100 hit. I resolve to keep this til after lunch.

I then go to Circa to use my comp at 8East. I start playing 3 line nickel DSTP DDB at the overhang bar. I hit early, and then go down. A 4OAK gets me +$50, but in my hunger, I stupidly decide to bump up to 5 line. I lose $100 and put in another large, the only thing I have in my wallet.

Halfway through my second hundred, I bump up to quarter 3 line hoping for my 4OAK that’s due. It never comes, but the third hundred comes out of my wallet.

Hangry and on full tilt, I proceed to lose all $300 that I had worked so hard to build in a matter of minutes.

I walk to a sketchy 7 Eleven for a free ATM and take $400 out of my gambling account, having to do it in two separate transactions to get around the withdrawal limit. I hope to do $200 Sunday and $200 Monday, getting in some table game play at the El Cortez, using my Match Play at the D, and checking out the Carousel Bar at Plaza.

I don’t make it out of the El Cortez without losing all $400. Chasing on Buffalo Platinum, which I put a $198 voucher into, does me in. I have multiple points where I could exit even, down $100, or down $200, but I keep going until I have nothing.

I hit an ATM at a souvenir shop having learned from my 7-Eleven jaunt but wanting money to use my match play. I pull $200.

I win my first match play, but lose the second. I decide to bet one more hand at $25 hoping to double my profit or break even; I break even when the dealer flips a blackjack in my last wager of the night.

I go back to my room just before 1am, shellshocked, dejected, and numb. I grab a “When the Fun Stops” pamphlet on the way up to the room.


I obviously have a lot to process and work through before I gamble again (likely at When We Were Young in October). Writing this was cathartic and helped me unpack how I adopted some of my toxic gambling mindsets. But this is just the first step.

I needed to experience the pain of this brutal loss to fully wake up to the reality that my gambling was not sustainable, and that it was heading down a slippery slope. The path forward is simple, but not easy; I need to (and will) unlearn my bad habits, recalibrate my expectations, rehone my discipline, reset my tolerance, and do a lot more introspection so that I can enjoy gambling in a sustainable and healthy way.

I decided to quit drinking and haven’t touched booze in over 18 months, so I know that I can do hard things when I put my mind to it. I am confident that I will come out of this stronger, and with the skills to better control my bankroll and enjoy even more time in the casino.

In fact, I’d bet on it.

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