Enjoy our best (and worst) gambling stories

Earlier this week, the Supreme Court paved the way for legal sports betting when they ruled, 7-2, that the ban on sports betting at the state level was unconstitutional. The decision doesn’t make gambling legal right away, but states will be able to legalize it on their own if they so choose.

Or at least make it more legal, if you know what we mean. Gambling on sports exists now, and not just in Las Vegas. If you’ve ever watched one of a few choice announcers calling an otherwise uneventful game and heard them get very excited all of a sudden for seemingly no reason, you know what I’m talking about.

So this will just make gambling easier for everyone, and maybe allow some of those enthusiast announcers to be a little more explicit about a backdoor cover or a bad beat. Since this isn’t the dawn of sports gambling, some SB Nation writers have entertaining personal experiences from past sports betting that more people may get the chance to replicate (or, sometimes, hopefully not) moving forward.

My dad went to Vegas one time and put a couple hundred dollars on the Penguins winning the Stanley Cup in 2017, many months before they actually did. We agreed we were going to share the bet. I never paid him my share, but I asked for half the winnings anyway. My overture was swatted away like a floater in the direction of Dikembe Mutombo. — Alex Kirshner

The summer after college I moved home and catered for a few months. One of the chefs (an awesome Italian guy) and I were close and were on the same crew that worked together a lot and were a well-oiled machine. One day, he saw me with my BlackBerry during staff dinner and asked if it got internet. I said yes, and he asked for a baseball score. So I obliged.

A few weddings later he asked me for another baseball score — except neither of the teams playing were the same as the first two teams he had asked about. I asked him which team he was a fan of since he was asking about so many, which is when he took out a tiny book and jotted the score down and said, “Asking you during our shift saves me so much time looking online later. I don’t have a phone with internet.” That book happened to have a whole lot of odds, lines, and names in it, which is when I realized that “fun Italian catering chef” wasn’t his only job.

So all that summer, after the weddings were over and we were waiting for straggling guests to leave, we’d split leftover bottles of wine and go over scores and sometimes he would throw me a few dollars. When he realized the ESPN app also provided odds he’d ask about those if he got a mid-shift call. Which is how I came to be a bookie’s assistant for a summer. — Whitney McIntosh

When Roy Hodgson was the manager at Fulham, my favorite soccer team, he kept his team very organized defensively. They wouldn’t attack all that much, and they’d sit back and defend well. Thus, a lot of their games ended in ties, especially away from home. So I started betting on that.

I, a college student in New Orleans at the time, opened an account at a gambling website, and for every Fulham away game, I would bet on a tie. At the time it seemed normal and smart, and I did make a little bit of money. But one morning I woke up at 6:30 a.m. to watch that week’s game and, sitting there by myself in my living room, the sun not quite up, I was struck by a horrifying realization.

Nate, I thought to myself, you are a college student in New Orleans, in the prime of your life, living in the greatest city on Earth. And every Saturday you are waking up early in the morning to sit by yourself and watch a soccer game played thousands of miles away, rooting for your favorite team in the world to tie.

That was it. I wised up and stopped. Don’t live like me. — Nate Scott

At an arcade in Japan, right around the time I was of legal Japanese drinking age and definitely not slightly under it, I was way into money matches. I played people for around five U.S. dollars per game in things like Street Fighter II, NFL Blitz 2001, Mr. Driller, Tetris, and quite a few others.

Eventually, I got on a pretty good winning streak on Blitz and was getting arrogant with my bets. I had around $200 in cash on me, and one person, whom I had absolutely destroyed in Street Fighter earlier, offered to play me for everything I had in Blitz. I was invincible. I could not lose. So I went for it, and I lost bad. Like extremely bad. Like 49ers beating the Broncos 55-10 in Super Bowl XXIV bad. Dejected, I left the arcade and realized it was the middle of the night, I had no money for a cab or a bus or anything like that and, furthermore, the trains in the area were not even running.

I wound up in a bar, where I managed to convey my situation to both the person tending bar and a few people around me. Or at least I thought I did. The person behind the bar, seemingly understanding of my plight and sympathetic, put a drink in front of me. I drank it. They put another drink in front of me. I drank it. This happened a few times, and when it was extremely late (or extremely early, I guess), I stood up to leave. Apparently, the person behind the bar did not quite understand, or perhaps I did not quite understand, but they became very irate once they realized I was not paying for what was ... seven or eight alcoholic beverages.

They called the police, who were very quick to show up, pick me up, take me to a station, and talk to me in, thankfully, English, about why I decided to order a bunch of drinks when I had no money. I was drunk, but managed to explain myself by the end of it, and also managed to explain that I had money at my hotel, which I needed help finding, and that it was all a misunderstanding. The police took me to the hotel, and the next day they returned, picked me up, took me back to the bar, and I paid my tab.

I think I am still allowed in Japan. — James Brady

I’m not much of a gambler (I mean, other than my unhealthy lifestyle and betting I won’t just die from a heart attack anytime soon), but I’m the kind of person who likes to show how much he believes in an athlete’s ability to overcome staggering odds that I make bold statements.

Like at a wrestling tournament when I turned to my 16-year-old daughter, who is a varsity wrestler at her high school, and I said to her that I thought her boyfriend at the time, Cooper, could beat the defending district champion (who was really, really, really good). She said he couldn’t. I said he could. We played that little game until I said that I bet $20 Cooper would win.

Without hesitation and to my surprise, my daughter shook my hand and then smiled. I chided her a bit for not having faith in her boyfriend’s ability — the week prior, after all, he won a match he shouldn’t have to bring home the victory that won the team district tournament. It turns out that my daughter was right however, and Cooper was destroyed in less than 20 seconds. I watched $1 per second melt out of my pocket and into her greedy, greedy hands. I won’t make the mistake of betting against her again. — Sam Eggleston

I had a fake I.D. from the age of 15. My mom still doesn’t know I had one. It was relatively easy with the drinking age being 18, so I obtained an “international student I.D.” card from a travel agency and all I needed for proof of age was my principal’s signature, and she was old and didn’t pay attention — but I digress.

Some friends and I went to a RSL Club, which is an Australian catchall institution of drinking, cheap food and gambling, with proceeds going to veterans. After several screwdrivers, I rocked up to a slot machine that had a cup of 20 cent coins sitting on it. Probably about $3 worth or so. I thought it was my lucky day — not only was I drinking cheap drinks, but I had some free coins to gamble with.

15-year-old James didn’t know the etiquette of gambling, or that this cup was being used as a marker to hold the machine — so he hit the slot a few times before it paid out the jackpot, which was at $210 at the time. James was ecstatic, the 80-something year old veteran who had been on the machine all night and returned from the bathroom to find a kid using his machine and hitting the jackpot was decidedly less enthusiastic.

It was that night I learned that old people used swear words too. It was also that night that I learned that elderly war veterans can still throw a punch. It was the next morning I learned how to explain a mysterious black eye to my mom. At least I had $210 in my pocket.
— James Dator

Do you have your own gambling story you’d like to share? Let us know in the comments.