Around 20 years ago, I was a freshman in a private college in Ohio majoring in Chemical Engineering, a nerd who loved to play video games, and about as introverted as a person could be. After a couple months of avoiding every major party in town, not leaving my room on the weekends unless I was going to grab some food, and playing way too many Warcraft II matches with people online I didn’t even know, a friend from one my chemistry classes asked if I wanted to drive up to Canada (Windsor specifically), and continued to explain to me how drinking and gambling were legal at age 19. At the time, I had no proclivity for gambling. I grew in a very god-fearing home of baptists, I never played poker with friends, never bought a lottery ticket before, and I didn’t have my first drink until I turned 18 (and it wasn’t my favorite thing in the world). That being said, being the shy person I was and hoping to develop some deeper friendships, I told my friend Matt (not his name), that I would go up with him for the weekend.

Being effectively broke college students, Matt went online for us and started seeking out the cheapest hotel room he could find for us. We ended up finding a Comfort Suites available at a nice rate and a few minutes later, we were confirmed and ready to go for the weekend. It was mid-December, cold as hell already back at home, and we hopped into my 1998 Honda Accord and started driving north for the border. After a reasonably short six hour drive up I-75, we ended up passing through Detroit and reaching the Ambassador Bridge crossing into Canada. A few questions from a border patrol officer later and we arrived quickly at our hotel and got settled in. Windsor is a very small town…nothing was more than a five minute car ride away. We dropped our bags off around 7pm, plugged the address into our GPS, and off to the casino we went.

After parking our car in the garage, we walked in, passed through security confirming our legality as a patron, and ventured onto the casino floor. The one thing I hadn’t really thought about before arriving was the most important part… cash. I think at the time, I might have had $800-900 in my bank account. Although that would have been a more than generous bankroll for a first trip, I started seeing the signs for cash advances from my credit card. After 5 minutes of debating it within my mind, I determined this was by far the smartest play as I could pay it off over time if I lost it, and even better, I had access to a lot more money than in my bank account (dumb…). I proceeded to the cash advance terminal and withdrew $1,500 USD to fund my weekend of debauchery, but I had forgotten the best part. This was a Canadian casino, which mean’t I needed Canadian Dollars! At the time, the exchange rate from CAD to USD was around 1.35:1, meaning my $1,500 in USD netted me over $2,000 from the nice cashier at the cage. After we both had some cash, we proceeded to the first table we saw with open seats.

Other than a vague understanding of the games on the floor, we were no experts. To say we were seeking out the best games on the floor would be a complete fabrication. After a couple laps around the casino floor, we ended up sitting down together at a Spanish 21 table. To be perfectly clear, we had no idea that Spanish 21 was a completely different game than traditional blackjack. Hell, I think it took 30 minutes to realize there were no 10s in the deck. With a lot of help from another player that joined us at the table, we played shoe after shoe, $15 on the main hand and $5 on the Match The Dealer side bet. We learned all the intricacies of the game like being able to double any number of cards, or rescuing your original bet after a bad double. After roughly two hours of play (and 3-4 drinks), the worst thing that could possibly have happened was occurring. I was winning… and big.After way too many times splitting faces, horrible doubles, poor strategy choices, and a chaotic betting philosophy, I had turned my $2,000 into almost $9,000 and I couldn’t lose. At some point in the night, I had reached a point of inebriation that I just couldn’t function any more, so my friend (who had lost his $500 buy-in) dragged me away from the table, back into our car, and drove us back to the hotel to pass out on the floor not even making it to the bed.

Waking up the next day, my head was pounding, stomach was killing me, smelt like shit and was ready to take a 2 hour shower with a beer. After getting up the energy to pick myself up the floor, take a shower and get myself dressed (in the same clothes as the night before), I was shocked to reach in my pocket and find $8,500 worth of casino chips. I was almost in disbelief, as my memory had wiped the nights events from my mind for the time being. I got with Matt and asked him if any of the chips were his, but he quickly told me that they were unfortunately all mine and he had gone broke early the night before. He started asking me if we should just head back to the US since he had no money left to gamble with and was kind of in a poor mood. I told him I was ok with that, but just needed to exchange these chips for cash before we left the country. A quick trip over to the casino, little time at the cashier, and the realization that you have to actually convert the money back to USDs and that exchange rate wasn’t as fun, and we were back in the car heading towards the border with about $6,000 in my pocket. Other than being freaked out in my mind passing through customs at the border with that much cash and drug dogs sniffing every car, we had a very pleasant drive back to our house.

A few days passed, and I just couldn’t shake the desire to want to get back up to Windsor as quickly as I possibly could. I texted Matt and asked if he wanted to go back up the next weekend, even offering to pay for the hotel room if he wanted to join. He said he couldn’t afford it, but wished me good luck. Being undeterred by the lack of a partner in crime, I made the trip back to Canada the following weekend and even splurged to stay at the Casino Hotel so I didn’t have to worry about driving back to the hotel after drinking. It was a beautiful property, nicer than anything I had stayed in up to that point in my life. Beautiful room, terrific food options… it was just a wonderful place to spend time. I walked up to a Spanish 21 table again with $2,000 CAD in hand and was not the same person as the week before. I was confident, bold and ready to attack. Although I still didn’t have basic strategy mastered for the game, I felt like an expert and never second guessed my choices. A few hours, and re-buys, later and I had lost all $6000 I won the weekend before, and another $500 USD I took out of the ATM. I was miserable, mad at myself, and didn’t even spend the night. I immediately got in my car after walking away from the table, heading home (all while forgetting to even grab my backpack out of my hotel room). I had gone from boom to bust in a week’s span.

I think for most people, at this time, it would have been such a humbling experience that they would likely have been scared away from the casino for a long time. I had no money to pay off my credit card bill, had no access to anything further on my credit card cash advance line, and honestly… I had little desire to go back for a while. However, the world changed when I received an email promotional mailer from the casino offering me $100 in free play, a free room, and a free buffet. You would have thought I received a hand written invitation from the Canadian Prime Minister with the level of awe in my eyes. The casino valued me so much that they were willing to pay for a $200 hotel room, give me their own money to gamble, and even pay for my food. I started brain storming ways to get enough cash to make a weekend trip work, and eventually had devised my master plan. I went online, applied for another credit card, and after begging a customer service agent on the phone repeatedly for help, was able to convince them to overnight me my new credit card so I had it for the weekend. This card had a $2,500 cash advance limit which seemed perfect for my big gambling weekend. Long story short, I took that $2,500 and turned it into a whopping $300, and ended up blowing that at the local strip club. Side note: Canadian strip clubs are significantly nicer than their US equivalent, and I highly recommend everyone swing by one before they die.

Here I was, 19 years old, with credit card debt of over $4,000 (and no good way to repay it), but I thought I was someone special in the eyes of the casino and gathered a taste of what it felt to be wanted by a casino. I had no idea how to handle the desire to play, the debt that had been accrued, the lies I was telling my friends, or the funds needed for future visits, but I knew I wanted and needed more. Stay tuned for Part 2 coming soon to discuss what changed over the next chapters of my life, my time employed as a dealer by that same casino, my growth as a gambler, what I have learned over the years, and how I got to where I am today. Thank you so much for reading.

To contact the National Problem Gambling Hotline, please call 1800-522-4700 or visit ncpgambling.org/chat

To read part 2 of my gambling addiction journey, Click Here.