How Not to Lose Your Shirt Gambling on Sports

Photo: Charles Krupa/AP/Shutterstock

So: If you live in New York, you can gamble on sports now! Suddenly, you can take out your phone and bet money — a lot of money — on any sporting event in the world. (If you live in New Jersey or a few other states, this is already old news.) Want to wager next week’s paycheck on handball? Your 401k on a table-tennis tournament in Russia? Your kid’s college fund on snooker? You can do it right now. You can do it so easily. 

In a very funny, very trenchant piece for Defector last week, writer Lauren Theisen details just how terrifyingly easy it is to lose everything quickly:

The frictionless way that I was able to give away my savings on there felt extraordinarily dangerous. Once the money was in my account, I could put up hundreds of dollars in less time than I’ve ever ordered a pizza, or even pulled up a movie to stream. In my very first time ever using the app, it took me six minutes to place four bets, and that was with a bit of strategic consideration on my part. I literally cannot think of a faster way for the average person to spend large sums of money, and now it’s just a few taps away for Americans with a smart phone in a growing number of states.

And Theisen is right. Sports gambling has gone from “taboo” to “illegal” to “legal” to “supported by sports leagues” to “a major part of those sports leagues’ revenue models” to “just a normal part of everyday life” so quickly it’s reasonable to feel, like Theisen, that your head is spinning. When the Supreme Court struck down a federal ban on sports betting in 2018, every league immediately got on board, partnering up financially with sports books so swiftly that many fans don’t realize just how much of the vig is going to Roger Goodell and Rob Manfred. Some teams, like the NBA’s Washington Wizards, are even installing sports books inside their arenas right next to the beer cart.

Whether this is a good thing is far from a settled question. You should know I personally think the legalization of sports betting is ultimately going to lead to a massive scandal, and probably several. But on a more human level, sports gambling can be personally destructive in a way that, say, weed or other recently legalized traditional vices are not. As NBA writer Ethan Strauss recently wrote, when the U.K. loosened gambling restrictions, a whole new class of serious problem gamblers emerged — and they’re still growing in number. We can argue that moral panics about gambling and other vices are overblown, but it’s undeniable that the number of Americans in this category will balloon along with the “destitution, divorces, and suicides” that, as Strauss noted, accompany them. And the leagues themselves will be a party to this suffering. For the first time I can remember, leagues aren’t just indifferent to their fans; they’re actively rooting for them to lose.

But there I go again, wagging my finger when I should be trying to help. This weekend, millions of sports fans were just trying to watch some historically great playoff football in peace, but after seeing 400 Caesars Sportsbook commercials featuring J.B. Smoove and Patton Oswalt, some portion of them were inspired to place a bet for the first time.

So here are some tips for first-time gamblers, the curious, the newbies … the suckers.

Know the rules. Do nothing unless you know the rules.

This may seem obvious, but if you open up the app and don’t know what the numbers in front of you mean, immediately close the app and do not open it again until you do. (Here’s a good primer.) It is hard enough to win at sports gambling when you know what you’re doing. Again, this may sound obvious, but it’s not like those J.B. Smoove ads are going to spend a lot of time explaining how things work to you. Remember the fundamental rule of sports betting: They rely upon you losing. Don’t make it any easier for them.

Don’t bet money you don’t have. Set limits.

The biggest mistake you can make as a sports gambler is to bet presumed future earnings before you have said future earnings. (Another way to put it: Don’t bet money you haven’t won yet.) Doing so is some serious Howard Ratner business. You’re not a shark. The app may try to make you think you are; that’s the whole business plan. Also: There’s no limit on the Caesars app to stop you from taking as much money out of your bank account as possible, so, uh, you better make one. Don’t talk yourself into making one … more … bet. Figure out a hard limit on how much you’re willing to lose. And then lose no more than that.

Do not pay anyone for advice. Ever.

The game is already stacked against you, and any earnings you take home will be the result of slow, incremental victories (see “grinding,” below) or making a big, huge, risky bet that happens to pay off (in which case, you’re just as likely to blow all that the next time you make a similarly risky bet; again, see Ratner, Howard). The idea of cutting into your already tenuous winnings by giving money to something named VegasWorm or GriecotheGreek is insanity of the highest sort. These are services that claim to have “inside” information if you’re just willing to pay for it. They don’t. You need to watch every penny to be a smart bettor. The last thing you need to do is to give those pennies who, despite their charming advertisements, are just guessing like the rest of us.

Don’t bet on your favorite team. Leave emotions out of it. 

Imagine if you were just a huge fan of the seven of diamonds in poker. Maybe it was a useful card to play in any given situation, and maybe it wasn’t. But its utility didn’t really matter, because you just loved that card, you grew up cheering for it, and you own a whole bunch of shirts with the seven of diamonds on the front of it.

You see where this is going. Betting on your favorite team, or betting with any emotion at all, is one of the quickest ways to lose. That doing it also serves as a way to commodify something as wonderful and eternal and ineffable as sports fandom — to turn something inherently personal and specific into something cold and desperate — is another reason to avoid it.

Grinding is the only way to win.

There are in fact people who make money from sports gambling. But they are, like John Turturro in Rounders, grinders. Strauss talked to a professional sports gambler named Rick who is able to make money, but it requires “time and resources” — which is to say more than just tapping away on your phone from the sports bar. The whole idea of “grinding” is to win small portions on the margins that add up to enough in the long run to make a living. You can’t win big. But you can win small if you space it out enough. Even the best professional sports gamblers are lucky to win 53 to 55 percent of the time. And you, I’m sorry to say, are not the best professional sports gambler no matter how much Jamie Foxx tells you otherwise. And even if you are …

The system is set up for everyone — even the top guys — to lose.

Rick explains to Strauss that “most of my time isn’t spent on getting an edge; it’s spent on figuring out ways to get a bet down.” Rick is known as a big winner, which makes him persona non grata at major casinos, many of which have smaller margins than the betting apps. So even if you end up being really, really good at this — and you won’t — you’ll hit a ceiling. It’s possible to make money at sports gambling. But it requires incredible discipline and focus and expertise … and the apps are set up precisely to evade anyone who has those three things. Remember this always: The game is set up for you to lose. That’s why every league wants to be a part of it! They all think you’re a sucker. And they’re right!

Don’t do it. Now you can’t say nobody ever told you so.

Look, I know I’m Cassandra here. I think gambling is bad for the world, bad for individuals, and bad for sports. I don’t necessarily think that means it should be illegal; I’m not the moral police here, and there’s something to be said for Adam Silver being slightly less likely to break your legs if you owe him money than the people you might have been betting with in the past. But this is a game you cannot win.

This does not mean the game cannot be fun. If you just find this enjoyable and are willing to lose small amounts and occasionally win big, you might have a blast. But know what you are doing going in because things can get out of hand in a hurry. You know how easy it is to order DoorDash? This is easier but more expensive, and you don’t even get any food out of it. Gambling is suddenly a part of everyone’s daily lives. You can do it, like, right now. But you shouldn’t. Please don’t. If it’s all fallen apart for you one day, come back and read this column. You cannot say you were not warned.

How Not to Lose Your Shirt Gambling on Sports