Sports Jillustrated

The Upside Of Sports Betting

Has the dissemination of online sportsbooks made it possible for anyone to hack the system? Let's assess.

By Jill Condon

Art by Malika Favre


My first experience using an online sports book was what one might consider “dangerous.” It was January 30, 2022. The Kansas City Chiefs were playing the Cincinnati Bengals in the AFC championship. Naturally, my eyes were drawn to the available bets with the highest odds. I’d decided to put down $1 on a couple of different exact scores (the odds on these ranged between +10000 and +30000). That season, Bengals kicker Evan McPherson was hands down the best in the league, so I selected a few scores with a 3-point difference in favor of the Bengals. Both QBs were pretty evenly matched going into the game. I figured the difference would lie in the hands (or feet, rather) of McPherson. I was right. Like magic, my $1 bet turned into a $225 payout. After I finished screaming, my emotional pendulum began to swing between, “Lucky me! I’m going to cash out and buy something cute for my room!” and “Oh my god. I never have to work again.”

Prior to this, the largest bet I’d ever won was $50 on the 2021 Super Bowl against my then-good friend-now boyfriend, who sent me my winnings on vemo with the message: “To the biggest slut in New York.”

Of course, this success was short-lived. Sure, bets would hit from time to time, but most of my bets were more like donations. Even so, there’s nothing more intoxicating than turning $2 into $20 whilst doing something you love (sitting on the couch watching tv).

“After I finished screaming, my emotional pendulum began to swing between, 'Lucky me! I’m going to cash out and buy something cute for my room!' and 'Oh my god. I never have to work again.'”

I am guilty of betting with my heart. On more than one occasion, I’ve placed bets fueled by the assumption that a player is going to “show out” because it was his mom’s birthday. Or because I knew his sister’s volleyball team was in the stands. Sometimes you wake up and just have a feeling. I have lost a good amount of money on the baseless conclusion that a certain player is “hungry.” I would say my betting philosophy is 70% logic, 30% emotion (sometimes the breakdown is closer to 55/45 depending on where I am in my menstrual cycle).

Curious about others’ endeavors in sports betting ahead of the upcoming NFL season, I spoke to three individuals of varying backgrounds about their experiences putting money on the line and whether or not they feel bettors can ever truly hack the system.

Player 1: Male, Early 30s, Average bet amount between $50-$100

If you can recall, what was the first bet you ever placed and what motivated you to place it?

I think it was when I was like 8 or 9, I was watching Ohio State on TV in my godfather’s barn and my dad let me bet like $5 on [Ohio State] to win. He and all his friends are degenerate gamblers so they were betting constantly, and I thought it was awesome that they got really excited when they won.

Did you continue on from there or did you stop and pick back up once you were older and understood the game more?

I got into it in my late 20s during the pandemic when I moved home. Watched football every day basically, and betting on it seemed logical since I felt like I knew a lot (I didn’t. I lost like $600).

What was your biggest hit and what was your biggest loss?

Biggest hit: $125 on a parlay last season, David Mills under 150 passing yards and AJ Brown touchdown. Biggest loss: $300 on the under on Raiders vs. Chargers in 2020 (lost on last play in overtime).

Gotta love AJ Brown. Have you ever fallen victim to betting with your heart/betting based on a gut feeling or do you primarily keep it pretty clinical?

I have a rule where I never mix the head and the heart. I refuse to bet on any team I want to win because I believe in jinxes. I try to be as clinical as possible generally.

Have you ever walked away from a win feeling as though you’ve “hacked the system”? If so, how long did that feeling last? When it comes to sports betting, do you think it’s possible for anyone to truly hack it?

Vegas always wins! There’s no hacking the system. Anytime I’ve won, it’s always been too close for comfort and always fleeting. The lines are set so well since Vegas is quite sophisticated by this point. The average person isn’t smart enough (much less has a big enough bankroll) to beat Vegas consistently. Doesn't make it not fun. It is weirdly cathartic and enjoyable to lose a bet, especially if it’s really close.

Player 2: Male, Mid-20s, Average betting amount between $1000 and $5000

What is your betting platform of choice?

Typically Stake but I use local sportsbooks as well (like a bookie). Bookies offer the best spreads. Large US sportsbooks ban/limit sharp action quickly. Basically – if you make money, you get banned

Do you typically stick with the same bookies or do you jump around?

The same. They have very good limits for me.

Are you saying that building a relationship with a bookie gets you better odds?

No, they're just more risky than corpo bookies.

“This isn’t going to have any background on me, right? Like this is fully anon, yeah?”

Are you saying that building a relationship with a bookie gets you better odds?

No, they're just more risky than corpo bookies.

I see. Can you tell me a little bit about your betting origins?

This isn’t going to have any background on me, right? Like this is fully anon, yeah?

Fully anon.

Can we talk about this another time?

Player 2 then declined to comment further on his betting practices. Is this because he wasn’t hesitant to elaborate on losses or because he didn’t want to share his hacks? The Betting Man works in mysterious ways (kind of).

Player 3: Female, mid-50s, Average bet amount under $10

Hi mom!

Hi honey! Wait, Kyle and dad are here, let me put you on speaker. Can you believe what happened to Aaron Rodgers?

We proceeded to talk about NFL week 1 and Aaron Rodgers’ failed pre-game manifestation tactics. I then told her the purpose of my call and we got down to brass tacks.

What got you into betting?

So, I got started because I never paid attention to commercials, and then one day I started paying attention to the commercials. I saw one for Fanduel and it looked like fun. Also, I love to win things. They don't have to be big things. I just love to win.

Does betting make games more engaging for you? Or is it kind of just something happening in the background?

The latter

Do you believe it’s possible for a bettor to ever “hack the system” or do you think it’s a lost cause?

I think it's reasonable to believe that someone could come out ahead. Last I checked I was breaking even. I bet emotionally but I think if someone really bet with the numbers I think they could. I always pick a Philadelphia team to win. Sometimes, if they're playing a really good team, I’ll bet for them to win but pick a realistic spread in case they lose.

What would you say to betting “puritans” who find it wrong to bet on your own team?

I like betting on what I know. It’s what I’m interested in. I think if I started expanding on other teams it would be too much. These are the teams I know the best so I will place bets on them because I really like to win. I would start getting very frustrated if I had to keep up with so many teams.

Will you be betting this NFL season?

Already have! So far I have one win and one loss.

Will we, the laypeople, ever truly find a way to hack into the world of sports betting? Probably not. Not financially speaking, anyway. The closest we can get to hacking the system is by not letting it ruin the integrity of the game. If you are able to lose a few bucks without muddying the waters that carry you away from everyday life, you’ve already hacked it.

More Articles: