11.24.2021

For the Boys: How Sports Gambling and Barstool Sports are Impacting a Generation

For many years, I’ve seen my students playing video games, messaging, and watching videos in school; but in the last year, I’ve noticed these pursuits have transformed from entertainment and socialization to that of side hustle. The apps have changed, the communities have changed, and so too have the negative externalities. Now when I catch my male students off task, I see them checking the balance of their favorite dopamine-inducing, risk-taking trading or gambling app (e.g. Robinhood or DraftKings). In a previous post, I wrote about the group of boys enamored with Robinhood, cryptocurrency, meme stocks, and the corresponding social media communities that impact them. This post is about the group of our boys that--thanks to legalized sports betting, a pandemic, and stimulus checks--have developed a side hustle in sports gambling.

These boys download gamified betting apps like DraftKings, FanDuel, and Caesar’s, cash in on their promotional offers, and then simmer in toxic social media networks led by powerful and incivil influencers like Barstool Sports. These actions and this network have turned our boys away from the knowledge and values we hope to impart as educators and parents. And while investing and gambling poses a risk to our young men, the far greater risk is the habits and actions that are inspired by communities of like-minded risk takers.

Sportsbooks 

In 2018, the Supreme Court legalized sports betting. Since that time, 26 states have enacted laws allowing the practice. As a burgeoning industry, sportsbooks (sports betting applications), compete to build their user base. The promotions they offer range from ludicrously simple bets (bet $1 and win $100 if your team hits a three pointer) and free bets (if you lose the bet you get reimbursed), to giving away money (match deposits up to $1,000). Two of the most popular fantasy football platforms-turned-sportsbooks, FanDuel and DraftKings, lose money every quarter despite steady growth because of how much they spend on sales and marketing. It’s a race to the bottom for these competing apps, leading some users to sign up for multiple books to cash in on these juicy promotions.

The entire business model of a sportsbook is to keep a user betting. In addition to entry promos, sportsbooks find unique ways to nudge users to get them online and betting. For example, sportsbooks use microtargeting to send advertisements and promotions to users that follow certain accounts on social media. If you follow a number of athletes from a certain sport, or a number of teams from a certain city, the sportsbooks will know which ads to show you and when to show them to you. And if a user stops betting, the promotions reappear in your social media feeds and inbox.

Sportsbooks are also paying to get their brands and offers in front of sports viewers on television. In less than two years of legalized online gambling, advertising has gone from $10.7 million to $154 million on local TV spots according to Nielson. They’re reaching national audiences too; it was disorienting tuning in to the World Series and hearing Joe Buck--a man who has been calling the World Series for over 20 years--reading promotions for gambling and encouraging betting. Sportsbook executives have painted their logos in stadiums, rinks, and ballparks around the country, and they’ve also placed their logos side-by-side with major sports franchises like the NFL, MLB and NBA as “official partners.” This exposure on social feeds, in stadiums, and on television makes users more likely to visit their sportsbook and place a bet. And it makes these brands palatable to young men, erasing some of the stigma associated with gambling.

Barstool Sports 

For our young men, watching sports and betting on sports are just two legs of the stool. The third is talking about sports, and no brand is reaching more of our young men than Barstool Sports. Whereas ESPN represents the business of watching sports, Barstool exists to amplify locker room chatter and frat house basement shenanigans. Frequently criticized for its sexism and bigotry, Barstool content could never be posted by any other national sports brand like ESPN, the MLB or Nike, and that’s what makes it resonate so much with the young, male fans. An apt microcosm for the raw and edgy nature of Barstool Sports is the expression it popularized, “Saturdays are For the Boys,” which encourages young men to engage in risky behavior to impress their friends (and other barstool fanatics) at the detriment of others (mostly women).

The CEO of Barstool Sports, Dave Portnoy, whips up an army of loyal supporters, called “stoolies,” against societal and ethical norms. Portnoy’s outsized megaphone amplifies his strong cocktail of racism and misogyny and creates space for others to join his reactionary worldview. In 2015, he embraced Trump for president writing, “I am voting for Donald Trump. I don’t care if he’s a joke. I don’t care if he’s racist. I don’t care if he’s sexist… I love the fact that he is making other politicians squirm. I love the fact he says s*** nobody else will say, regardless of how ridiculous it is.” Like Trump, Portnoy is currently embroiled in several sexual assault scandals. And central to his appeal is his refusal to apologize or admit mistakes. Instead, he fights back, steering his army of stoolies--including a man he hired to wage harassment campaigns for him--at anyone who critiques him or Barstool.

Last year, Barstool Sports launched a gambling site, Barstool Sportsbook, to parlay its success attracting young, male sports fans to their brand. Whether our boys gamble with Barstool or not, the Barstool feed has emerged as a key soundtrack to sports gambling for a generation of our young men.

Impact on our Young Men

For young men, sports are meant to be fun--a way to exercise and connect with friends--but nowadays (thanks in large part to sportsbooks and Barstool) sports have become a side-hustle. When you feel like your money and your identity are on the line, you act in ways that change your character and that can negatively impact your community. I’ve written previously about how our boys participate in sports for their own stats, highlights, and college signing rather than for camaraderie, community, and character building. The same thing is happening to watching sports. Our young men research players, stats, and games to place a bet, rather than to cheer on a team or be part of a great game. The same thing is happening when talking about sports. This generation watches sports with a second screen in hand (e.g. TV and Phone), which means that periodically throughout a game, one can place a new bet or hunt for off-the-field content that will enhance the watching experience.

What unites the changes described above is a powerful psychological trick exploited by gambling and social media companies alike called variable rewards. Psychologists discovered that when subjects receive intermittent rewards, they find it extremely challenging to disrupt a behavior. Whether pursuing promos in a gambling app, placing a bet, pulling to refresh your social media, or posting on social media and awaiting the likes, these actions release dopamine in the brain, signaling to your brain that something awesome might happen. The way our boys are participating in sports currently demands a tightening of the dopamine-infused feedback loops. Instead of betting on an NFL game, they bet on every single drive (more dopamine and more variable rewards). Instead of consuming Barstool content, they try to make their own (more chances for likes, comments, and shares). The slow and steady stream of sports betting invites riskier decision-making. Of course, the escalation of risk-taking behavior extends beyond the individual into our communities.

These changes to our boys’ behavior include a shifting of values. For example, when our boys get together over sports, their interests remain selfish as everyone has his own bet (his own side hustle). Even if your (or a friend’s) team lost, as long as you win the bet you declare victory. At the same time, there’s an agreement that groups of boys are bound together (For the Boys), and that they should feel empowered to make mistakes as young men, including harassment, peer pressure, bullying, and bigotry. Our boys call it anti-PC (political correctness), society calls it toxic masculinity. Egged on by Barstool and its CEO, young men resist acknowledging others’ feelings and refuse to make any apologies. Stoolies dox, they brigade, and they never apologize for acting how they’ve been told by Barstool that men should act.

Status and Side Hustle 

In sports and in life, this generation of boys seek to optimize their time and knowledge. If you’re going to be researching sports, watching sports, and playing sports, you might as well turn that knowledge into some cash. The same can be said for boys that are tuned into the conversations about which fan did something outrageous, which athlete has a beautiful girlfriend, or which broadcaster shared his politics. Being in on the joke, and being able to provide your “take” on what you consumed on social media bestows a similar kind of status. And if there’s an easy bet or a hilarious post that you miss, FOMO is a powerful motivator; you’ll be sure to be in on the next one as it reflects your identity and status.

When you bet on a game, friends ask for your “take” (in person and on social media). If you win your bet, friends view you as knowledgeable about sports, and a savvy side hustler. Many leverage their status to create personal brands by sharing their takes online or selling merchandise to follow in the footsteps of their favorite influencers. Those boys who can turn an interest into a side hustle gain status and respect. This status can get to one’s head. In a recent Insider piece that lays out the assault allegations against Portnoy, one 19-year old college student who was a victim of Portnoy’s advances attributed his predatory behavior to the fact that he felt emboldened by his status. Status changes behavior. As adults and mentors, we need to keep an eye on it.

Community & Values 

Not all of our boys who like sports are “stoolies” loyally following Barstool; many of them check in and out for the pizza reviews and the memes. But if you play sports in high school or college, you know someone who has “For the Boys” souvenirs, and you’ve heard someone deploy the misogynistic slogan to justify engaging in risky behavior and/or treating someone else poorly. Over time, the lines between social media and sports gambling become blurred. In the same way friends, FOMO, and the drive to optimize one’s time can convince young men to place a bet, edgelords and sh*tposters that populate social media feeds with Barstool-like content slowly make an impact (see Irony Poisoning).


Blurring the lines between online sports life and reality, Barstool uses its influence to normalize all the gut-level behaviors associated with being a manly man and a sports fan. They make it okay to objectify women, to make bigoted comments, and to peer pressure friends. For example, Portnoy and stoolies are infamous for the sexual harassment of female sports analysts. There’s not a lot of research or editing in their posts because the strongest push of the Barstool brand is to create content. To this end, Barstool, Portnoy, and stoolies are a responsive community, seeking to take and share content from their audience. They create numerous smaller brands including those that encompass different colleges and even college conferences (e.g. Barstool NESCAC), which inspires stoolies to try to do something on brand for Barstool that will get them featured on their local Barstool handle.

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What scares me most about the sportsbook--Barstool Sports tandem is that despite one’s most egregious gambling decisions, and despite one’s most egregious behavior, there’s always someone to validate that person’s decision-making as long as it’s “For the Boys.” And there’s always someone who has done worse--just check the Barstool feed. In the same way that the sportsbooks are in a race to the bottom to hook users, our young men are in a race to the bottom to align themselves the most with the Barstool brand.

As an educator, I wonder about the opportunity cost associated with sports gambling. What else could our young men research assiduously? From what other communities could they network and learn? And as an educator, I worry about the impact on surrounding constituencies. I worry our young men’s dopamine-fueled, risk-taking is leading to unhealthy relationships and unhealthy decision-making, which disproportionately affects our young women.

I recently caught up with a former student--now in college--who caught himself gambling on European basketball on a Tuesday at 9 AM in his religion class. To his credit, he quit. Unfortunately for him, it’s still in front of his face all the time. I recount this story to implore readers to reach out to the young men in their life. Ask questions, listen without judgment, and be a mentor.